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Cottages, Villas, Apartments in Healdsburg
Holiday Rentals
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California (CA)
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Cottages, Villas, Apartments in Healdsburg
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Internet or Wifi (180)
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Kid friendly (155)
Pet friendly (64)
Smoking allowed (5)
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Holiday Rental House (171)
Condominium/Apartment (12)
Cabin Holiday Rental (0)
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Waterfront (10)
Boat Available (2)
Private Chef (0)
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Distance from
5 mi
Gracianna Winery
Dry Creek Vineyard
Alexander Valley Vineyards
Gary Farrell Winery
Seghesio Family Vineyards
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183 rentals
in Healdsburg.
Newly Refurbished! Nest Cottage at ru's Farm.
36
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
26
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
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Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
52
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
27
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
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Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
26
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Healdsburg Wine Country Getaway with Panoramic Valley Views -5 min from downtown
215
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
28
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
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Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.
269
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views
22
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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Chalk Hill Cottage Close to Wineries
25
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Healdsburg Cottage Walk to the Plaza, Workspace
52
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS
5
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Secluded Valley Retreat
102
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Wooded Restful Retreat, with broad scenic views, outdoor dining
277
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE
24
Holiday Rental House
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4 bedrooms
7 bathrooms
Sleeps 10
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Redwood River House--Serene Riverfront Cottage  In Healdsburg, Views, Kayak
13
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Luxurious Wine Country Oasis--Hot tub, Bocce court, cornhole and firepit!
16
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
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B - Wine Country Getaway
19
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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luxuriously appointed new large guest suite in a landmark Victorian
30
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views
21
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Healdsburg Home with Magnificent Vineyard View by RedAwning
12
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
5
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Dry Creek Cottage - Healdsburg
45
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 2
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Luxe Guest Suite in Dry Creek 5 Mins From Town!
4
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Three-Bedroom Hotel Suites in Downtown Healdsburg
15
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Modern Sophisticated Private Luxurious W/Views & Hot Tub
196
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Healdsburg House - Chiquita Road - Hot Tub - Private
14
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Charming Riverfront Cabin – Just 10 Minutes from the Plaza!
7
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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Stunning Vineyard Views, Top Location, Clean, Safe
12
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Winter sale! Getaway & stay on the vineyard, hot tub with 5 ensuite bed/6 bath
13
Holiday Rental House
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5 bedrooms
6 bathrooms
Sleeps 10
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Perfect romantic getaway for two! Private retreat in the countryside.
13
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
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Private Vineyard Haven--walk to the HBG Square!
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 4
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Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country
10
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Flora Vina - Country Home with Vineyard Views
3
Holiday Rental House
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3 bedrooms
6 bathrooms
Sleeps 8
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Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!
106
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball
103
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 10
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Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown
17
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Modern, recently built home with stunning pool & beautiful views; 15 min to town
14
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 12
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Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg
177
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
15
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Mountaintop Respite Overlooking Vineyards: Pool & Spa - 2-4 Guests
18
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 4
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Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi
11
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 8
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Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
9
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 12
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Healdsburg Studio - Immaculate Brand New!
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
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Beautiful Studio Getaway in the Heart of Wine Country
81
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Healdsburg Studio - Vineyard Views!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Magnolia Ranch Vineyards | Historic house in Healdsburg with lovely private yard
10
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza
10
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Downtown Healdsburg Loft - (30 day minimum rentals only)
6
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Great outdoor space, fire pit & gourmet kitchen minutes from downtown Healdsburg
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Showing results 1-50 of 183
Frequently Asked Questions about Healdsburg
Do any holiday rentals in Healdsburg have a pool?
Yes, here are some popular holiday rentals in Healdsburg that have a pool:
Newly Refurbished! Nest Cottage at ru's Farm.
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
See all holiday rentals with a pool in Healdsburg on Tripadvisor
Do any holiday rentals in Healdsburg have internet access?
Yes, here are some popular holiday rentals in Healdsburg that have internet access:
Newly Refurbished! Nest Cottage at ru's Farm.
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
See all holiday rentals in Healdsburg on Tripadvisor
What are the best pet friendly rentals in Healdsburg?
The best pet friendly rentals in Healdsburg are:
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
See all pet friendly holiday rentals in Healdsburg on Tripadvisor
What are some great rentals in Healdsburg that are kid friendly?
Some of the most popular kid friendly rentals in Healdsburg are:
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.
Beautiful Coop Cottage overlooking vineyards. Three minutes from downtown!
Fitch Mtn Lookout- Gorg & Comfy!Pets-Walkable Russian River-Spa under the stars!
See all kid friendly holiday rentals in Healdsburg on Tripadvisor
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