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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Healdsburg holiday homes

Terrace/patio

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

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Property grounds

2. 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 HK$1,601
HK$7,288 total
includes taxes & fees
22 Sept - 23 Sept
Wildflower
Coffee/tea maker, fridge, microwave, oven

3. 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 HK$1,020
HK$3,042 total
includes taxes & fees
29 Sept - 30 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

4. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (23 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is HK$1,173
HK$3,893 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor dining

5. 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 HK$4,436
HK$9,666 total
includes taxes & fees
22 Sept - 23 Sept
River View Lodge - Hot Tub and Tastings Included
Terrace/patio

6. 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.
The price is HK$5,084
HK$10,421 total
includes taxes & fees
13 Oct - 14 Oct
Healdsburg Plaza Gem-Hot Tub and Tastings Included
Terrace/patio

7. 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 HK$1,800
HK$5,259 total
includes taxes & fees
24 Sept - 25 Sept
Russian River Retreat: Private Beach & DogFriendly
Dining

8. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is HK$1,295
HK$2,916 total
includes taxes & fees
21 Sept - 22 Sept
Wine Country Cottage Escape
Outdoor pool, a heated pool

9. Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Healdsburg
9.6 out of 10, Exceptional, (193 reviews)
"Great location and cozy home."
United States
Kelly B.
The price is HK$4,119
HK$7,634 total
includes taxes & fees
28 Sept - 29 Sept
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Outdoor dining

10. Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (69 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
The price is HK$2,745
HK$7,523 total
includes taxes & fees
28 Sept - 29 Sept
Redwood Riverfront - Hot Tub and Tastings Included
Terrace/patio

11. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (68 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Coffee/tea maker, fridge, microwave, oven

12. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (39 reviews)
"Had a great time staying at Vineyard Vue"
United States
Grace N.
Vineyard Vue - Wine Tastings Included
A heated pool

13. Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!

Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Healdsburg
9.4 out of 10, Exceptional, (13 reviews)
"Fun and relaxing. "
United States
Helen M.
The price is HK$12,246
HK$21,350 total
includes taxes & fees
20 Sept - 21 Sept
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Outdoor dining

14. 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 HK$1,812
HK$4,286 total
includes taxes & fees
20 Sept - 21 Sept
Russian River Brew-cation Home
TV, fireplace

15. 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, (76 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is HK$2,707
HK$5,374 total
includes taxes & fees
22 Sept - 23 Sept
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Dining

16. 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 HK$4,064
HK$8,666 total
includes taxes & fees
21 Sept - 22 Sept
Elegant Vineyard Living at a Private Wine Country Estate
Outdoor pool, a heated pool

17. Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Healdsburg
10.0 out of 10, Exceptional, (73 reviews)
"We had an incredible stay at Bella Vista. It was a short ride to downtown Healdsburg and the property was beautiful and extremely well stocked. We were a group of eight women and all raved about the gorgeous grounds and surrounding views. I would highly recommend staying here. "
United States
Angell & P.
The price is HK$14,121
HK$21,377 total
includes taxes & fees
14 Oct - 15 Oct
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
A heated pool

18. Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (23 reviews)
"Loved our stay."
United States
Vanessa R.
The price is HK$3,839
HK$7,500 total
includes taxes & fees
24 Sept - 25 Sept
Farpoint: Heated Infinity Pool, Mountain Views
Exterior detail

19. 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, (67 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is HK$12,513
HK$18,902 total
includes taxes & fees
11 Oct - 12 Oct
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Exterior

20. 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 HK$6,749
HK$13,947 total
includes taxes & fees
13 Oct - 14 Oct
The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included
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

Healdsburg Inn on the Plaza, A Four Sisters Inn

Healdsburg Inn on the Plaza, A Four Sisters Inn

10/10 Excellent
"Everything about this stay was perfection. We couldn’t ask for a better stay. We will return and recommend to friends and family."
Victoria 2-night trip
Posted 1 day ago
Healdsburg Inn on the Plaza, A Four Sisters Inn

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
811
Accommodation
232 Vacation Homes
Lowest Price
HK$2,916
Highest Price
HK$21,377

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