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
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 vacation homes

Dining

1. 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.
Cozy Riverfront Cabin - Beach Access & Wood Stove
Terrace/patio

2. 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.
The price is AED 595
AED 1,434 total
includes taxes & fees
21 Sep - 22 Sep
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Outdoor dining

3. 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 AED 2,315
AED 4,904 total
includes taxes & fees
6 Oct - 7 Oct
Redwood Riverfront - Hot Tub and Tastings Included
Property grounds

4. 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 AED 940
AED 3,656 total
includes taxes & fees
21 Sep - 22 Sep
Wildflower
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
Outdoor dining

6. 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 AED 1,904
AED 4,234 total
includes taxes & fees
28 Sep - 29 Sep
River View Lodge - Hot Tub and Tastings Included
Coffee/tea maker, fridge, microwave, oven

7. 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 AED 489
AED 1,437 total
includes taxes & fees
17 Sep - 18 Sep
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

8. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AED 606
AED 1,365 total
includes taxes & fees
21 Sep - 22 Sep
Wine Country Cottage Escape
Terrace/patio

9. 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 AED 2,838
AED 5,467 total
includes taxes & fees
28 Sep - 29 Sep
Healdsburg Plaza Gem-Hot Tub and Tastings Included
Terrace/patio

10. 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
TV, fireplace

11. 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 AED 1,275
AED 2,528 total
includes taxes & fees
22 Sep - 23 Sep
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Outdoor dining

12. 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 AED 702
AED 1,843 total
includes taxes & fees
21 Sep - 22 Sep
Russian River Brew-cation Home
Dining

13. 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 AED 1,903
AED 3,972 total
includes taxes & fees
22 Sep - 23 Sep
Elegant Vineyard Living at a Private Wine Country Estate
Coffee/tea maker, fridge, microwave, oven

14. 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.
The price is AED 4,266
AED 7,484 total
includes taxes & fees
30 Sep - 1 Oct
Vineyard Vue - Wine Tastings Included
A heated pool

15. 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, (12 reviews)
"Fun and relaxing. "
United States
Helen M.
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Exterior

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

17. Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
Eastside Eden - Pool, Hot Tub and Tastings Included
Exterior detail

18. 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 AED 5,273
AED 8,278 total
includes taxes & fees
16 Sep - 17 Sep
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
A heated pool

19. 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 AED 1,797
AED 3,578 total
includes taxes & fees
30 Sep - 1 Oct
Farpoint: Heated Infinity Pool, Mountain Views
Outdoor pool, a heated pool

20. 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 AED 6,611
AED 10,009 total
includes taxes & fees
14 Oct - 15 Oct
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
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

Hotel Healdsburg

Hotel Healdsburg

10/10 Excellent
"Wonderful location, cute rooms, great breakfast, wine tastings in the afternoon."
Summer 3-night trip
Posted 15 hours ago
Hotel Healdsburg

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