A garden pathway lined with white roses leading to a building with a stone facade and a window.

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Healdsburg holiday homes

Property grounds

1. Wildflower

Wildflower
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 £577
includes taxes & fees
9 Sept - 10 Sept
Wildflower
Coffee/tea maker, fridge, microwave, oven

2. 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, (23 reviews)
"very nice space "
United States
kevin c.
The price is £314
includes taxes & fees
1 Sept - 2 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Outdoor dining

3. 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)
"View was lovely. The Hot tub was great. Beds were very comfy!"
United States
Julie B.
The price is £1,081
includes taxes & fees
26 Aug - 27 Aug
River View Lodge - Hot Tub and Tastings Included
Terrace/patio

4. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (48 reviews)
"Great location and charming cottage. "
United States
Christopher T.
Healdsburg Plaza Gem-Hot Tub and Tastings Included
Terrace/patio

5. 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.
Russian River Retreat: Private Beach & DogFriendly
Dining

6. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is £280
includes taxes & fees
2 Sept - 3 Sept
Wine Country Cottage Escape
TV, fireplace

7. 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, (74 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is £454
includes taxes & fees
17 Aug - 18 Aug
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Outdoor dining

8. 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.
Russian River Brew-cation Home
Exterior

9. Rivers Breeze - Wine Tastings Included

Rivers Breeze - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (20 reviews)
"Lovely place, exactly as described. Really nice place to sit & listen to nature, access to river, well-appointed, easy, and the owners are responsive and easy to work with."
United States
Seppo H.
Rivers Breeze - Wine Tastings Included
Outdoor dining

10. Heron House - Hot Tub and Wine Tastings Included

Heron House - Hot Tub and Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (30 reviews)
"Perfect home base for a Mother’s Day weekend in Sonoma County. Between the peaceful natural setting and the proximity to town and surrounding wineries and hiking, it was ideal. Great stay at Heron House."
United States
James L.
Heron House - Hot Tub and Wine Tastings Included
Exterior

11. The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (7 reviews)
"Pool, spa and fire pit all were used a lot and enjoyed. House was beautiful with many wonderful amenities."
United States
KJ C.
The price is £1,837
includes taxes & fees
25 Aug - 26 Aug
The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included
Terrace/patio

12. Chateau Chemise -Pool, Hot Tub, Wine Tastings

Chateau Chemise -Pool, Hot Tub, Wine Tastings
Healdsburg
The price is £1,433
includes taxes & fees
23 Aug - 24 Aug
Chateau Chemise -Pool, Hot Tub, Wine Tastings
Dining

13. 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, (84 reviews)
"We enjoyed our stay. We had a lovely girls weekend and had no issues. The owner was very responsive and helpful."
United States
Avani S.
The price is £608
includes taxes & fees
14 Aug - 15 Aug
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Dining

14. 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 £945
includes taxes & fees
23 Aug - 24 Aug
Elegant Vineyard Living at a Private Wine Country Estate
A heated pool

15. Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (21 reviews)
"Loved our stay."
United States
Vanessa R.
The price is £801
includes taxes & fees
7 Sept - 8 Sept
Farpoint: Heated Infinity Pool, Mountain Views
Exterior

16. Santini Farmhouse - Wine Tastings Included

Santini Farmhouse - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (57 reviews)
"Enjoyed our stay. Winery visits were a real plus."
United States
polly b.
The price is £1,345
includes taxes & fees
10 Sept - 11 Sept
Santini Farmhouse - Wine Tastings Included
Exterior detail

17. 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, (66 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is £1,191
includes taxes & fees
15 Aug - 16 Aug
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Dining

18. 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, (12 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is £320
includes taxes & fees
19 Aug - 20 Aug
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Terrace/patio

19. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (35 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is £345
includes taxes & fees
30 Aug - 31 Aug
Somms Rest ⎮ Designed. Curated. Peaceful.
Smart TV

20. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (40 reviews)
"Great hosts. Very accommodating. Clean and beautiful property. Great timely communication with hosts."
United States
Neeraj
The price is £393
includes taxes & fees
30 Aug - 31 Aug
Serenity at the Russian River
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.
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Top Healdsburg Hotel Reviews

Appellation Healdsburg

Appellation Healdsburg

10/10 Excellent
"We had an incredible weekend at the Appalachian. We were thoroughly impressed by the exceptional hospitality and the beautiful environment that’s created. It was a truly special weekend, especially since we were celebrating a special event.. Chef Charlie Palmer and Chef Reed provided us with an exceptional tasting menu. Sommelier Tess’s wine pairing and list were nothing short of remarkable. GM Brian’s hospitality was truly exceptional. Our waiter Dominic was a true professional. There are many other members of the team who deserve our thanks as well."
Joseph 1-night trip
Posted 21 hours ago
Appellation Healdsburg

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
621
Accommodation
248 Holiday Homes
Lowest Price
£280
Highest Price
£1,837