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Holiday Rentals nearby Chalk Hill Winery

10300 Chalk Hill Rd, Healdsburg, California 95448-9558
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    All 33 Rentals in Healdsburg
    7.1 kilometres from Chalk Hill Winery
    Studio, 3 Bathrooms, Sleeps 10 Quick View
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    Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)1 / 29
    (4)Very good
    4.4 kilometres from Chalk Hill Winery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    7.1 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    5.8 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2016
    the house is fabulous and the location is perfect.minutes to town and lots of wineriespeaceful setting and cool clean house
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    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,...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    7.9 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Balcony
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    7.8 kilometres from Chalk Hill Winery
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Healdsburg, Sonoma County
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    7.7 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Mountain Views
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to heavenly Healdsburg and Hilltop's Vista Villa! This gated 2-bedroom, 2-bath luxury Tuscan inspired villa is located only 3 miles from the historic Healdsburg plaza on one hillside acre near the top of the east side of Fitch mountain and is the only home this close to the top! This...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    7.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Buena Vista is a Wine Country getaway on the Russian River with Spectacular Views just a short drive from Healdsburg Plaza. When you reserve this 2400 square foot, 3 bedroom, 3 bath home, beautiful, panoramic views are just one of the many amenities you will be able to enjoy. The Buena Vista is...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5.9 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Xanadu Healdsburg Luxury Vacation home in Healdsburg. In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek, Alexander Valley and Russian River Wine Regions. The home is just Five minutes from the Healdsburg Plaza Square with dozens of Winery Tasting Rooms, Award...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    6.1 kilometres from Chalk Hill Winery
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    The perfect location for your Healdsburg getaway. Three separate buildings including a three bedroom house, a bright and airy studio shed with an outdoor shower, and your own wine tasting bar in our family barn. Modern design in a rustic setting right across the road from J Winery and Rodney Strong...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    5.9 kilometres from Chalk Hill Winery
    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
    Kid friendly
    Smoking allowed
    About this property
    Stunning Modern Villa on eight acres, Located in exclusive Shiloh Estates, only minutes to down town Healdsburg and world class Wineries. Extremely private, Triple gated in a natural setting next to famed Mayacama Gold Course. Fully furnished, high end high thread count linens. 4th bedroom is...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 7 Bathrooms, Sleeps 8
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Terrace
    • Children's Pool
    • Washer
    • Balcony
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The biggest Sonoma Coast lodging option is the Three-Bedroom suite, a large furnished family suite with space for up to eight guests that features one king-sized bed in the master bedroom, one queen-sized bed in the guest bedroom, two twin-sized beds in the third bedroom and one queen-sized Murphy...
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    Windsor, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    6.1 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Private Garden
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Armida Vineyards Cottage Escape to your very own piece of California wine country at this Healdsburg vacation rental, where you'll enjoy sweeping vineyard views and an ideal location for exploring one of the region's most beloved towns. Dramatically situated in the middle of a 12-acre vineyard,...
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    Windsor, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5.4 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Washer
    • Balcony
    • Children's Pool
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for families and small groups traveling together, this option is equipped with one king-sized bed in the master bedroom, two twin beds in the guest bedroom and one queen-sized Murphy bed in the living room. With space for up to six people, this comfortable family suite features a separate...
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    Windsor, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.6 kilometres from Chalk Hill Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Central Heating
    • Mountain Views
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leslie Creek House Treat yourself to an unforgettable wine country getaway at this four-bedroom Santa Rosa home, a stunning Sonoma County escape with a sparkling interior, a fun-filled media room, and picturesque outdoor spaces that include several decks, patios, and a private swimming pool....
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    Fulton, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    5.4 kilometres from Chalk Hill Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Balcony
    • Washer
    • Wi-Fi
    • Children's Pool
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Each condo is outfitted with one king-sized bed in the master bedroom, plus queen-sized Murphy bed in the separate living area. Ideal for two to four guests, this comfortable rental features a fully equipped kitchen, private terrace or patio and gas fireplace. You'll also have high-speed Internet...
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    Windsor, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Wine Country Townhouse1 / 11
    (3)Average
    4.5 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    My family of five and I have had the pleasure of renting this Townhouse five different summers. We head to Nor Cal every summer and this place has it all. The home is spotless...
    Reviewed 7 February 2018
    We left hot Florida and had a great time in California wine country. Instead of a usual hotel we joined our friends at this townhouse. After long days of sight seeing we came...
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    About this property
    Upstairs downtown condominium on the Windsor Green, walk to coffee, restaurants, shopping. Concerts in summer. Main floor has beautifully decorated living room with fireplace, Flat screen TV, DVD, sofa, chairs, dining area and kitchen and half bath. Deck looks over to historic railroad station and...
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    Windsor, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Windsor, CA Cottage in Sonoma's Wine Country1 / 21
    (6)Excellent
    5.2 kilometres from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Garden
    • Grill
    • Washer
    • Central Heating
    • Parking
    • Outdoor Dining Area
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2016
    A fantastic 2 bedroom guest house. Warm, comfy, incredibly well appointed. You will want for nothing. If you are in the area, this is the place you want to stay.
    Reviewed 19 October 2015
    Justine provides a well-appointed and stylish accommodation in the heart of the wine country. The cottage is immaculate and everything one might need to prepare meals at-home...
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    About this property
    The Carriage House is a 800 sq/ft single level cottage in a unique country property setting, within walking distance to our sleepy Town Green where there is a seasonal farmer's market, music and movie nights. Our home sits on a level private acre and boasts mature trees for shade, open sunny areas...
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    Windsor, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
    View all property information
    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
    View all property information
    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
    View all property information
    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5.0 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Mountain Views
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Loch Haven Retreat Find sleek, modern elegance among the golden hills, renowned vineyards, and majestic oaks of Sonoma County at this country home just outside of Santa Rosa and Calistoga. Stunningly situated on more than three acres at the end of a private drive, this dog-friendly property...
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    Location Information
    Fulton, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5.4 kilometres from Chalk Hill Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple 3-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and the...
    View all property information
    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Close to Healdsburg Plaza with Vineyard Views!1 / 17
    (2)Excellent
    2.6 kilometres from Chalk Hill Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Wi-Fi
    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 2019
    This beautiful Sonoma vacation rental made all the difference in my wine country getaway!! The home is so cozy, comfortable and very clean!! With all the comforts of home at...
    Reviewed 27 January 2019
    This Fantastic house is a wonderful place to stay if you want to go to the wine country have an amazing getaway either during the week or weekend. t is just over an hour from...
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    About this property
    This newly remodeled 3 bedroom home is the perfect wine country getaway with breathtaking vineyard views! We offer our guest free VIP wine tasting experiences at some of the best boutique wineries in Sonoma. We also have free wine tasting vouchers to some of the best wine tasting rooms in...
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    Location Information
    Windsor, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    6.0 kilometres from Chalk Hill Winery
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. Bookings at this home include a 24-hr buffer between guest stays through June 2020. * Got some wine lovers to impress? Book a vacation in this spacious country home in Santa...
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    Santa Rosa, Sonoma County
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    5.0 kilometres from Chalk Hill Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A freshly remodeled two bedroom guest unit. With your own separate driveway,entrance and backyard, you will have complete privacy. The space is full of light and was designed with your comfort in mind. From the linens to the art - we took great care in creating a retreat for you. Enjoy...
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    Windsor, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    5.4 kilometres from Chalk Hill Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Patio
    • Hot Tub
    • Terrace
    • DVD Player
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The WorldMark Windsor resort is located on ten acres with multiple three-story buildings, all with elevators. Nestled into the Russian River Valley in Sonoma County, Windsor is a small town with deep roots in farming and, more recently, winemaking. You'll enjoy the area's family-owned wineries and...
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    Location Information
    Windsor, Sonoma County
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    INR
    India
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