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Our top choices for Healdsburg holiday homes

1. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
United States
Tina A.
The price is £267
includes taxes & fees
1 Dec - 2 Dec
Wine Country Cottage Escape

2. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is £281
includes taxes & fees
17 Nov - 18 Nov
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

3. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (30 reviews)
"Our favorite place we have stayed in at the Russian river by FAR! Wonderful lakeside cabin feel. It feels like people have actually lived there and loved the home (unlike most rental properties that have clearly never had a resident). Great location right by downtown."
United States
Savannah M.
The price is £351
includes taxes & fees
15 Nov - 16 Nov
Cozy Riverfront Cabin - Beach Access & Wood Stove

4. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (24 reviews)
"very nice space "
United States
kevin c.
The price is £267
includes taxes & fees
1 Dec - 2 Dec
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

5. Sonoma Summer Oasis: Sauna, Fire Pit & Games

Sonoma Summer Oasis: Sauna, Fire Pit & Games
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is £719
includes taxes & fees
15 Nov - 16 Nov
Sonoma Summer Oasis: Sauna, Fire Pit & Games

6. Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
10.0 out of 10, Exceptional, (1 review)
"Love this place so much! Will rent it every year for my birthday if they’ll let me!"
United States
Anna K.
The price is £433
includes taxes & fees
17 Nov - 18 Nov
Russian River Retreat: Private Beach & DogFriendly

7. Tranquil Retreat with Pool, Hot Tub, & Game Room

Tranquil Retreat with Pool, Hot Tub, & Game Room
Healdsburg
The price is £673
includes taxes & fees
15 Nov - 16 Nov
Tranquil Retreat with Pool, Hot Tub, & Game Room

8. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"Wonderful vacation and location. "
United States
Leslie M.
The price is £842
includes taxes & fees
16 Nov - 17 Nov
River View Lodge - Hot Tub and Tastings Included

9. Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
Forestville
The price is £490
includes taxes & fees
16 Nov - 17 Nov
Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

10. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
The price is £370
includes taxes & fees
16 Nov - 17 Nov
Russian River Brew-cation Home

11. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (50 reviews)
"Great location and charming cottage. "
United States
Christopher T.
The price is £1,118
includes taxes & fees
23 Nov - 24 Nov
Healdsburg Plaza Gem-Hot Tub and Tastings Included

12. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is £744
includes taxes & fees
22 Nov - 23 Nov
Elegant Vineyard Living at a Private Wine Country Estate

13. Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Healdsburg
9.6 out of 10, Exceptional, (68 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is £1,248
includes taxes & fees
18 Nov - 19 Nov
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

14. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (77 reviews)
"Our stay was very comfortable."
United States
Kim R.
The price is £438
includes taxes & fees
16 Nov - 17 Nov
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

15. Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (85 reviews)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
The price is £453
includes taxes & fees
15 Nov - 16 Nov
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

16. Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (24 reviews)
"Loved our stay."
United States
Vanessa R.
The price is £780
includes taxes & fees
1 Dec - 2 Dec
Farpoint: Heated Infinity Pool, Mountain Views

17. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is £300
includes taxes & fees
2 Dec - 3 Dec
Forestville Redwood Escape

18. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (23 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
United States
Greg K.
The price is £310
includes taxes & fees
15 Nov - 16 Nov
2BR Bungalow - Russian River & Wine Country

19. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (16 reviews)
"Nice place, great location, had everything we needed. Helpful and prompt communication by the host. This was a great base for exploring the area."
United States
Rebecca I.
The price is £311
includes taxes & fees
16 Nov - 17 Nov
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

20. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (31 reviews)
"Lovely place, very clean, in quiet surroundings."
United States
Brigid
The price is £125
includes taxes & fees
23 Nov - 24 Nov
Cobb Mountain Chalet King Size Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Healdsburg

Stroll between tasting rooms in this charming wine country plaza where vintners pour small-batch Pinot Noir and Zinfandel. Bike through rolling vineyards in the morning, then spend afternoons browsing farm-to-table restaurants and artisan shops with locally-made olive oils.

A vineyard sign with "Dry Creek Vineyard" written above a stone archway.

Top reviews in Healdsburg