Holiday Rentals in Healdsburg
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Bedrooms
Bathrooms
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Property type
Distinctive Features
152 rentals in Healdsburg.
Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Wooded Restful Retreat, with broad scenic views, outdoor dining
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Modern Wine Country Cottage in Historic Healdsburg, Premiere Location
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Modern Sophisticated Private Luxurious W/Views & Hot Tub
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Healdsburg Wine Country Getaway with Panoramic Valley Views -Close 2 downtown
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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9 minutes to Healdsburg Plaza: 1.6 Acres of Privacy at End of Country Road
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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luxuriously appointed new large guest suite in a landmark Victorian
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Healdsburg Cottage Walk to the Plaza, Workspace
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Luxury Vineyard Estate Guest House
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern, newly built 5 BR home with beautiful views and 50 acres of privacy
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Dry Creek Cottage - Healdsburg
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Casa Chiquita - 3 Bedroom, 3 bath newly remodeled home with spa and pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Tanda Tula, Wine Country Sanctuary
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Secluded Valley Retreat
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Updated cabin, right on Russian River, amazing river access & location!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Superb Healdsburg Location, Spectacular Views, Minutes to Town
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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River View Lodge--Riverfront Getaway in Healdsburg
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Newly Listed 5BR/5.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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120-acres of peace and tranquility, 10 minutes from downtown Healdsburg
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern View Home - Pool, hot tub, large deck, BBQ - 1 mile to Healdsburg Plaza
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Redwood River House--Serene Riverfront Cottage In Healdsburg, Views, Kayak
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Dry Creek Vineyards ~ *Heated* Pool, HotTub, Barn!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spectacular View Estate 5min Away
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Healdsburg Hilltop Retreat :: Craftsman detail, modern comforts & stunning VIEWS
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Dry Creek Valley Home and Vineyard
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Creek Front Vineyard, West Dry Creek Healdsburg CA
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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New Contemporary Home in the Heart of Sonoma Wine Country.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rendezvous Under the Oaks-Pool & hot Spa
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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VineHaven- Spa, Gardens, & Spectacular Vineyard Views
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private 3 Bed + Cottage Wine Country Estate With Pool And More
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Vineyard View!! SPA, Close to Plaza!- 3br/2ba (up to 8 guests)
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Stunning Views�Pet-Friendly� Kayaks avail�♀️ Semi-Private BeachLux Spa
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vineyard Vista, 4Bd/3Ba, Healdsburg, Spa, Ping Pong
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Riverside Cottage: Access and River Views
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-friendly home on 10 acres w/private hot tub, English garden, patio
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Cabin on Fitch Mountain
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 152
Frequently Asked Questions about Healdsburg
- Yes, here are some popular holiday rentals in Healdsburg that have a pool:
- Healdsburg, 4BR/4BA, Pool, Internet, Fireplace
- Healdsburg, 5BR/5.5BA Estate, Pool, Hot tub, Fire pit, Games
- Dry Creek Cottage - Healdsburg
- Yes, here are some popular holiday rentals in Healdsburg that have internet access:
- Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views
- Healdsburg, 4BR/4BA, Pool, Internet, Fireplace
- Healdsburg, 5BR/5.5BA Estate, Pool, Hot tub, Fire pit, Games
- Some of the most popular kid friendly rentals in Healdsburg are:
- Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views
- Healdsburg, 4BR/4BA, Pool, Internet, Fireplace
- Healdsburg, 4BR/2.5BA, hot tub, Fire pit, Bocce Ball, BBQ