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Holiday Rentals in Healdsburg, CA

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    ₹ 42,233 Average
    ₹ 67,000+
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    Travellers to Healdsburg are booking October dates now. Secure your holiday home today, and have the perfect trip.
    1 / 43
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 19
    5 of 5 stars (17) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 28
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • Central Heating
    • Grill
    • Patio
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    • Pet-friendly
    • Child-friendly
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    • Smoking allowed
    • x
    About this property
    Luxurious 500sft Contemporary Cottage with French Doors opening onto the landscaped garden with sitting area, Kitchenette, sky-lighted stone shower, Living Room& Pilates Studio 3 blocks from the Plaza perfect home away from home. Makes this your personal sanctuary whether you are staying for the... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 8
    5 of 5 stars (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    • Satellite TV
    • Shared Outdoor Pool...
    • Hot Tub
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    • Mountain Views
    • Air Conditioning
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    DEAR POTENTIAL GUEST: PLEASE CHECK CALENDAR BEFORE INQUIRING ABOUT AVAILABILITY - IT IS ALWAYS CURRENT. THANK YOU!!<BR><BR>Since its opening in 2008, guest reviews confirm Dry Creek Villa to be a truly exceptional, idyllic retreat! We consistently rate 5/5 stars from prior guests. Among the... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 1 August 2014
    My wife and I were looking for a quite, secluded retreat to totally unwind, we have found it. A modern, contemporary villa, on top of a ridge, with views in every direction. Only...
    5 of 5 stars Reviewed 25 April 2012
    This place was completely procured by my friend, Andrew, with the smallest of input from the other members of the party. We were all very impressed with the property, both in...
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    1 / 24
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor...
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    • Pet-friendly
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    • x
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    About this property
    This Mediterranean home has casual elegance with expansive decks, patios, spa and a SOLAR HEATED SWIMMING POOL surrounded by flagstone and plenty of outdoor seating. The 4 bedrooms are all Kings, quite secluded both from each other and the common living spaces. All suites have private full... View all property information
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    Healdsburg, Sonoma County
    1 / 20
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
    • Patio
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    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our apt. is nestled in the heart of the gorgeous Dry Creek Valley wine country, 10 minutes away from Healdsburg and its many wineries, acclaimed restaurants, and shops galore. the apt. is 1150 Sq ft with 2 bedrooms, kitchen/great room, and deck/BBQ. We have 8 acres with organic gardens, raised... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 3 August 2016
    We were two couples that stayed in the barn on a Saturday night whilst passing through Healdsburg. The accommodation was a large kitchen, lounge, outside deck, bathroom and 2...
    5 of 5 stars Reviewed 24 June 2016
    Our stay in Healdsburg was so lovely, and the Stromberg B&B was a wonderful part of it! Beautiful pool, lovely grounds, a tennis court and basketball hoop - even a 3-hole golf...
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    1 / 37
    5 of 5 stars (2) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Housekeeping...
    • DVD Player
    • Mountain Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Inspired by the Villa Gallici in Aix-en-Provence, Villa Aix Vineyards combines traditional, French cottage warmth with fresh, contemporary farmhouse flair.Nestled on a serene 20-acre vineyard in the Alexander Valley appellation of Sonoma's gorgeous rolling hills, this private estate offers all the... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 11 April 2016
    We rented this house for my girlfriend's bachelorette weekend and it was absolutely beautiful! We were a large group but never left crowded as the house was very spacious, giving...
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    1 / 28
    5 of 5 stars (16) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Mountain Views
    • Central Heating
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our cottage is one of the best priced rentals right on the river with a big spa. It is priced the same or lower than other rentals across the street or up Fitch Mountain. There is a big difference being on the river, the large deck and dinning room have river views and lots of natural lights. The... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 2 weeks ago
    Spent our anniversary in this lovely home and it had everything we needed!!! Loved coming back here after a long day of wine tasting. Either sitting on the deck taking in the...
    5 of 5 stars Reviewed 21 July 2016
    Great place to spend time and enjoy the river. The cottage overlooks the Russian River and has everything you need to relax, cook up a meal or play in the water. Back deck is...
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    1 / 28
    5 of 5 stars (5) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Waterfront
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Patio
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Nestled in a picturesque redwood grove on the banks of the Russian River, only 3 miles from historic Healdsburg Plaza, Redwood Tree House is one of the most enchanting vacation rental homes in all California Wine Country. The charming Main House and romantic "La Casita" guest cottage provide a... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 13 September 2013
    I don't think I can say enough about how wonderful our trip to the Redwood Treehouse was! My husband and I were travelling with friends of ours, another couple, and this house was...
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    1 / 10
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Grill
    • DVD Player
    • Satellite TV
    • Porch
    • Central Heating
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Very conveniently located at the beginning of Dry Creek Road and minutes from downtown Healdsburg. Children welcome and pets considered. The house is a newly updated 1950's ranch house that has been tastefully and simply decorated. As you walk up the redwood porch and into the house, you enter... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 19 December 2014
    This house is tucked away on a tree lined street within Dry Creek Valley. It is a stone's throw from both Healdsburg and the Valley's Wineries which is a valuable asset as a...
    5 of 5 stars Reviewed 18 September 2014
    We are 5 women who meet several times a year for Wine Tasting Weekends, where cooking, relaxing and wine tasting are the focus. This is our 5th house rental in this area and is...
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    1 / 17
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Balcony
    • Mountain Views
    • Patio
    • Grill
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The pristine Chalk Hill valley here in Healdsburg is where this lovely attached studio is located and only 12-14 minutes drive to downtown Healdsburg, and 5-7 minutes to downtown Windsor featuring: Separate entrance with deck and views, gas bbq Queen size bed, fully equipped kitchen, private... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 9 December 2015
    Great place in Chalk Hill area. We were within 45 minutes of Armstrong Redwoods and within 20 minutes of any Sonoma winery we wanted to see. Took ten minutes or so to get to...
    5 of 5 stars Reviewed 9 January 2015
    We had a very nice stay with Tony and Julie. It's a lovely studio with all the amenities you need. It's convenient to many wineries, Windsor and Healdsburg. The owners were...
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    1 / 30
    5 of 5 stars (10) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • Mountain Views
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    'Mona, a name given to house by our daughter when she could not say 'Sonoma,' is a four bedroom/four bath, completely remodeled home including a one bedroom/one bath guest house in the heart of Dry Creek Valley in Healdsburg, California. Our vacation home sits on one acre nestled among the vines... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 14 September 2015
    Mona was just as warm & welcoming as the photos showcased. Celebrating our Mother's 90th, it was the perfect location to enjoy time together as family- plenty of games to enjoy...
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    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Patio
    • Private Outdoor...
    • Washer
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This remarkable 3-bedroom, 2.5-bathroom house is well-equipped to give you the getaway of a lifetime in the Alexander Valley area. With room for 6, an exquisite backyard oasis, and easy access to attractions, this home leaves nothing to be desired. As soon as you arrive at this abode, you’ll know... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 28
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This restored country home sits in the Alexander Valley near the famous Jimtown store, and looks across to and around vineyards. Just 7 minutes from Central Healdsburg, many wineries are nearby such as Fieldstone, White Oak, Sausal and Hanna, and Calistoga is within a 20 minute drive. As you drive... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 16 July 2013
    We stayed at the Jimtown House for a girls getaway. It was absolutely wonderful! The house is stunning, beautifully furnished, well stocked and on the most magnificent grounds...
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    1 / 29
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Washer
    • Satellite TV
    • Mountain Views
    • Children's Pool
    • Patio
    • Wi-Fi
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Situated on 2.5 acres, just minutes from the quaint downtown of Windsor and about 10 minutes from the Healdsburg square, Woody Creek Retreat is at the pinnacle of convenience while offering the serenity of a quiet country luxury farmhouse. Ideal for families, couples, or friends wanting a to... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 33
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
    • Hot Tub
    • Balcony
    • Central Heating
    • Grill
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Drive down a tree-lined road. Vineyard is on left, beautiful gardens and bocce court in front, and garden area to the right in which to sit or stroll. Walk into a dramatic entry, and you'll see formal living room and dining rooms on the right, with a half bath across the hallway. To your left,... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Air Conditioning
    • Washer
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Sauna
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This distinctive and luxurious vacation home, with views and a private beach, offers 3 King Bedrooms, plus Queen guestrooms. The prime riverfront location in Healdsburg lies in the heart of Sonoma Wine Country, near the point where the Russian River flows through three world class wine growing... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 23
    4.5 of 5 stars (2) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Mountain Views
    • Internet Access
    • Satellite TV
    • Sauna
    • Central Heating
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Firefly Lodge is one of 4 luxurious riverfront vacation homes owned by Wine Country Lodges, located in beautiful natural settings in Sonoma Wine Country. (For information on all four visit the WineCountryLodges website.) Firefly Lodge is a warm and welcoming retreat, enjoying peaceful and... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 1 October 2014
    We had 8 people staying for a wedding in September in the Alexander Valley. The Firefly lodge was a perfect place to stay. It has a wonderful view of the Russion River. More...
    4 of 5 stars Reviewed 3 January 2013
    Wonderful place. I would suggest going when the weather is warmer so you can take advantage of the kayaks, hot tub and sauna. Beautiful home on the Russian River. Be prepared to...
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    1 / 21
    5 of 5 stars (25) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Central Heating
    • Washer
    • Balcony
    • Satellite TV
    • Patio
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Affordable Wine Country Home (up to 6 guests) and Country Cottage( for two guests) surrounded by 15 acres of vineyards. Both vacation homes are in private locations on one 15 acre gated estate. Location is everything! In Healdsburg everyone wants to be near the Plaza--we are just 1 & 1/2 miles... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 19 August 2014
    We enjoyed our stay in the farm house. It was a beautiful spot, we were surrounded by vineyards. The picture is a bit misleading, it was taken from a spot on top of a hill so...
    4 of 5 stars Reviewed 29 July 2014
    We can't say enough about the beautiful location of the house, just spectacular! The house was clean and everything you needed was provided, so from that standpoint, 10 out of 10...
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    1 / 37
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Patio
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    All of the living at West Dry Creek View is at the back side of this beautiful modern minimalist country property. Three private acres offer a large in ground 22' x 60' swimming pool and large concrete hot tub amid gardens, emerald green lawn, and vineyard views galore, all less than ten minutes to... View all property information
    Location Information
    Healdsburg, Sonoma County
    4 of 5 stars Reviewed 15 March 2015
    Beautiful location on west dry creek road making it convenient to get to many wineries and downtown Healdsburg but also secluded enough to get away from the hustle and bustle...
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    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy the beauty of Healdsburg from the middle of a 12-acre vineyard at this three-bedroom vacation cottage, where you'll have your very own scenic deck and enclosed yard! Gorgeously situated just three miles from central Healdsburg in the heart of California wine country, this bright and... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 14
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Hot Tub
    • Outdoor Dining Area
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    River View Lodge appeals to guests with its spectacular riverfront setting, spacious river view deck, charming décor, exceptionally comfortable beds and linens, outstanding cleanliness, and quality amenities. River View features private river access, and includes kayaks, paddles and life jackets.... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 25 August 2015
    We loved staying at the Northwoods Lodge and would like to return again sometime. The property was very clean and well maintained, and the location, view, and river access are...
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    1 / 14
    3.5 of 5 stars (7) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • Air Conditioning
    • Mountain Views
    • Satellite TV
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    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This lovely little cottage is really a unique and hard to find category for a few guests or 2 couples. Furnished smartly, and priced right, this cottage offers big amenities for the vacation home traveler. Set on one acre, there is off street parking through gates, a hobby vineyard, and outdoor... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 26 May 2015
    Communication with owners was quick and easy. The place is close enough to town to walk. If you want to wake up and see vines, you won't be disappointed. Beads were super comfy...
    3 of 5 stars Reviewed 11 June 2013
    Yes, this cottage is comfortable and well furnished. Full kitchen, great hot tub, comfortable beds, lovely setting in a real vineyard. BUT: it is located off a fairly busy road...
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    1 / 29
    4 of 5 stars (2) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Outdoor Dining Area
    • Internet Access
    • Waterfront
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This 3 story, 3+ bedroom classic river retreat has beautiful river views, and it's own dock. It is only a mile from Healdsburg and guests can take an easy and enjoyable walk to the Plaza, around which all the excitement and activity revolve in this picturesque, world class wine growing region.... View all property information
    Location Information
    Healdsburg, Sonoma County
    4 of 5 stars Reviewed 22 August 2015
    The house (Old River Lodge) is beautiful and comfortable, but the parking is a bit tricky. The only real problem was major construction going on next door. The loud hammering...
    4 of 5 stars Reviewed 14 July 2014
    Spent a week at the Old River Lodge with both daughters and their husbands and had a most enjoyable time. The lodge is a three story home on the bank of the Russian River, with...
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Internet Access
    • Secure Parking
    • Satellite TV
    • Washer
    • DVD Player
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Spend your vacation in the heart of Healdsburg, CA at the Moorish-inspired Cypress House. Beautiful tiles, an interior courtyard, and an incredible view of downtown and beyond from the top floor terrace make this property unique to wine country. Located at the edge of a small shopping center, it... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 13
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
    • Washer
    • Grill
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Patio
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Cute, fully furnished, 3 bedroom/2 bath farm house in the city of Healdsburg. 10-15 minute walk/ 5 minute bike ride / 3 minute drive to Downtown Healdsburg. Few miles away from over 100 wineries! 30 DAY MINIMUM per Healdsburg Zoning Laws but we require longer stays based on seasonality THERE ARE... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Air Conditioning
    • Patio
    • Internet Access
    • Parking
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Experience the best of California wine country at this two-bedroom Healdsburg home, where you'll enjoy a private outdoor hot tub, two patios and a deck, and an ideal location close to restaurants and tasting rooms. This dog-friendly retreat sits on a tree-lined property two miles north of central... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Sauna
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Patio
    • Parking
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Nestled between the Russian River, Alexander Valley, and Dry Creek Valley. Wine regions, the hotel is just minutes away from over 150 world renowned wineries, dining, arts, culture and outdoor activities. Attractions nearby a lso include the Healdsburg Center for the Arts, River Rock Casino,... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 30
    5 of 5 stars (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
    • DVD Player
    • Outdoor Dining Area
    • Mountain Views
    • Grill
    • Parking
    • Satellite TV
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Isabelle's Maison Guests: " Please read for full pricing"$ Zinscape’s Private Cottage and Garden Room are set among the Dry Creek Valley , with over 60 wineries and vineyards in the heart of the wine country. You pull down driveway to the doors of both seperate rooms which are adjacent to each... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 23 July 2016
    Loved the 4 days here in such a beautiful area of Ca nestled in the vineyards of Healdsburg Ca. The owners were super friendly and gave us hints on where to visit, eat and see...
    5 of 5 stars Reviewed 19 September 2015
    We rented the cottage and our friends stayed in the garden room. Both rooms were quite lovely and all that we expected. The location was convenient yet very private and quiet...
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    1 / 44
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Wi-Fi
    • Central Heating
    • Balcony
    • Mountain Views
    • Grill
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    2nd floor: 11 foot ceilings. Beautiful, gourmet kitchen with stunning views. Kitchen is equipped with a Thermador 6 burner (and grill) gas stove top and double electric oven. Butcher block counter tops. Dishwasher, Professional quality knives and cookware. Large microwave. Spacious walk-in pantry.... View all property information
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    Healdsburg, Sonoma County
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Washer
    • Central Heating
    • Mountain Views
    • Patio
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This 3 acre property is located in world famous Alexander Valley, has fantastic views of the vineyards/mountains and has its own hillside vineyard (our guests will be able to enjoy a bottle of cabernet sauvignon grown from the hillside vineyard during their stay). The house is a great combination... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 11
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Wi-Fi
    • Private Garden
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Riverstone Ranch is truely a multi-family property. A location which caters to several generations with traditional main house, or modern 2BR/2BA "coup" or "Oak Tree House", each offers something a little different, all against gorgeous Russian River views and less than 5 minutes to downtown... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 10
    4 Bedrooms, 7 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Private Garden
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Stunning Modern Villa on eight acres, Located in exclusive Shiloh Estates, only minutes to down town Healdsburg and world class Wineries.<BR>Extremely private, Triple gated in a natural setting next to famed Mayacama Gold Course. <BR>Fully furnished, high end high thread count linens. <BR>4th... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 18
    3.5 of 5 stars (3) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    ENJOY...a fabulous vacation with old man river, at the RiverHouse, where the Redwoods meet the Russian River. With direct river access and its own private beach, this very special riverfront home is located just minutes from downtown Healdsburg, yet a world away, nestled on a wooded knoll on North... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 22
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This beautiful Healdsburg Estate home, located 3.5 miles southeast of the Downtown Plaza is a 3800 sq. ft. two-story custom home with central heat/AC, 4 bedrooms and a private sunroom with a convertible queen sofa making the 5th bedroom (combining to sleep 10), 3 beautiful full baths and 1 half... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 23
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Air Conditioning
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Very well located in Healdsburg, the ‘crown jewel’ of Sonoma County’s Wine Country, and under 2 miles from the historic Plaza, this 2000 sq. ft. vintage main house and 640 sq. ft. pool house, originally built in 1898 has many beautiful upgrades including central heat/AC, and combines the beautiful... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 9 October 2015
    Our group included three couples....perfect place to stay! The pool is great, very comfortable and clean throughout.
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    1 / 21
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Very well located on a ½ an acre with the back fence on the edge of Dry Creek Valley’s West Wines Vineyards, this beautiful ‘home away from home’ awaits you and your guests! First, be welcomed by a lovely landscaped yard out front with mature plantings and a small lawn which you can enjoy while... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 9 August 2016
    This place was very spacious and very clean. The kitchen had all the amenities and appliances we was not expecting to necessarily see (blender, kitchen-aide mixer, salad...
    5 of 5 stars Reviewed 22 June 2016
    We absolutely loved our stay at Maison de Soleil! The home was gorgeous and provided us with all the comforts and amenities of home. The location was perfect for easy access to...
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    1 / 24
    4 of 5 stars (4) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool...
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Nestled on 10 acres in the prestigious Chalk Hill appellation of the Alexander Valley, this rustic, beautifully renovated and newly furnished, 5br/3.5ba, 3200 sq. ft., two-story lovely home with central heat/AC, sits on a wooded knoll just above the vineyards. There is a separate pool house on the... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 31 July 2016
    I loved it and I'd love to come back again. I love Sonoma County.The rooms were very comfortable. I just adored the pool. The weather was perfect. I can't wait til next year.
    4 of 5 stars Reviewed 11 July 2016
    This is a wonderful house for groups. The common space offers many seats. The hot tub is large enough for 7 people. There is a BBQ and lots of outdoor seating for families to...
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    1 / 20
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Location, location location! Perfectly situated only 3 miles (a 5-7 minute drive) from the charming and historic Healdsburg Plaza, this fabulous, custom three-bedroom home abounds with special eco-friendly features. You will be wowed by this modern home’s beautiful open-beamed cathedral ceiling,... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 31
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Private Outdoor...
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Hot Tub
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ideally located on 7 hillside acres, in the famed Dry Creek Valley, this absolutely stunning, new, Modern Wine Country Home is a spectacular retreat nestled in Mother Nature’s paradise, with forever easterly views of the Dry Creek Valley. This magnificent architectural marvel was designed by John... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 21
    5 of 5 stars (19) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Patio
    • Washer
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Tertulia at Amber Ridge – where good friends and family gather in stunningly beautiful, peaceful surroundings to enjoy each other’s company over great food and wine. Deep relaxation, pleasant conversation, laughter and joy ensue! Tertulia is a fabulous two-acre Wine Country sanctuary surrounded on... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 23 August 2016
    We loved this house for so many reasons I can hardly list them all. We love to cook and the kitchen was fantastic for just that. We had six adults and five children (also...
    5 of 5 stars Reviewed 7 April 2016
    We recently spent a long weekend at Tertulia with a group of friends and had an absolutely fabulous time. The house is great...spacious, warm and inviting. The kitchen/dining...
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    1 / 20
    5 of 5 stars (11) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Spectacular Two-Story Tuscan Villa Estate Home - 4br/3ba (2-8+ guests) w/ Spa, Decks & Views, on 5 Gated, Secluded Vineyard Acres. At the end of a private tree lined country lane, ‘under the Tuscan sun’, vacation in your ‘own private villa’. Nestled in charming, upscale, and historic... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 15 February 2016
    We had a group of 6 and everyone was very pleased with our stay. The location is away from downtown, so it's a good place to stay if you want total, complete privacy and a...
    5 of 5 stars Reviewed 17 October 2015
    We loved our vacation in this luxury Tuscan villa. We chose this property for two reasons: we had three couples travelling and wanted three bedrooms/bathrooms that were comparable...
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    1 / 19
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Newly Renovated Healdsburg VineHaven - 3br/2ba (up to 8 guests, children welcome, small lapdogs considered) w/ Spa, Gardens, & Spectacular Vineyard Views Very well located at the north end of Healdsburg and the beginning of the famed Dry Creek Valley and vineyards, this newly renovated 50’s... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 13 August 2014
    Location could not have been better. The house and property were well done and very clean. Had everything we needed and more. Only one little thing we didn't like was the...
    4 of 5 stars Reviewed 21 June 2012
    We just returned from a long weekend trip to Russian River Valley for a wine tasting trip & 50th birthday celebration. I found VineHaven online while looking for a house rental...
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    1 / 22
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8+ guests, children welcome, small lapdogs considered), in the vineyards. Shaded by a 100-year-old oak tree, this very special home ‘lives’ on 30 vineyard acres and is off Dry Creek Road, just one mile west of the north end of charming, upscale,... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    With a spectacular location on 12 beautifully landscaped and maintained acres, in the foothills between Santa Rosa and Healdsburg, Montebello Heights Estate is a newer Tuscan-themed, 4200 sq. ft. 4br/3.5ba, two-story home, with central heat and AC, and many custom features and special amenities,... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 16
    4.5 of 5 stars (5) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Parking
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the best of two worlds, the peace and tranquility of ‘country living’ among the vineyards and wineries of the Russian River Valley, and the convenience of being only five minutes from the historic Healdsburg’s Plaza. Bella Terra Healdsburg is an upscale, and modern appointed three bedroom,... View all property information
    Location Information
    Healdsburg, Sonoma County
    5 of 5 stars Reviewed 23 August 2016
    I rented this house with a group of 7 and it was PERFECT! The property is secluded, the pool is amazing and the beds are comfortable. The location is removed from Santa Rosa, but...
    3 of 5 stars Reviewed 11 September 2014
    I was staying at Bella Gia with my husband and a few friends. We were in Healdsburg for our friends' wedding. The house is in an extremely convenient location to downtown...
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    1 / 20
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Ideally located on 6 acres with a 2-acre Zinfandel vineyard, overlooking the West Dry Creek, this gated Estate sits atop a small hill with incredible panoramic views of the W. Dry Creek Valley and Mount St. Helena. This lovely ‘lady among the vines’ is spacious at 2500 sq. ft. with central... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautifully located, perched just above the Russian River, on S. Fitch Mountain, this Vintage 1927 river home has been beautifully renovated and modernized with central heat/AC, new dual-paned windows, high open-beamed ceilings, and all the modern conveniences while still maintaining its vintage... View all property information
    Location Information
    Healdsburg, Sonoma County
    1 / 21
    5 of 5 stars (3) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Satellite TV
    • Washer
    • Grill
    • Hot Tub
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Only 3.5 miles northeast of Healdsburg’s historic plaza, this stunning, nearly new, custom 3br + bonus room / 2.5 bath “castle” is a 4 acre vineyard estate property that is perched on a knoll and surrounded by vineyards with a beautiful view of the foothills of the Alexander Valley wine growing... View all property information
    Location Information
    Healdsburg, Sonoma County
    Healdsburg Vacation Rentals

    Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.

    Healdsburg a Slice of Paradise

    Small town charm, beautiful landscapes and outstanding weather are just a few of the trademark qualities that make Healdsburg so popular. Healdsburg combines five-star cuisine, rolling hills and world-acclaimed wine growing appellations for an experience you will never forget. When it’s time to relax at the end of the day, why stay in a cramped hotel when you can enjoy the comforts of home in one of our rental cottages, houses or cabins?

    Lots of Activities

    If you love the vibrant outdoors and colorful festivals, you will love Healdsburg. In April, you can help harvest roses and distill them into fragrant rose oil and rosewater as part of the Classic Perfume Rose Harvest & Distillation Tours. An annual sea food dinner at the Healdsburg Fire Department is also in April. From February to June, enjoy the "Russian River Good Old Days" exhibit at the Healdsburg Museum. And on the first Friday of the month, Williamson Wines sponsors an Epicurean Dinner at the Dry Creek Kitchen at Hotel Healdsburg.

    Food, Wine and Fun

    Speaking of eating, you won’t want to miss the chance to dine at Healdsburg’s amazing restaurants, including Affronti, Agave Mexican Restaurant &Tequila Bar, Thai Orchid Cuisine, Willi's Seafood & Raw Bar and Zin Restaurant & Wine Bar. And don’t forget to visit the beautiful wine country all around you, featuring names like Alexander Valley, Chalk Hill, Dry Creek Valley, and Russian River Valley. We’re here to help you make the most of your visit to Healdsburg. Let us help you find the perfect cozy cottage, cabin or house to make your stay in Healdsburg one you will always remember.