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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Healdsburg vacation homes

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

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 ￥18,915
￥121,619 total
includes taxes & fees
Sep 1 - Sep 2
Wildflower
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

2. 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 ￥76,477
￥180,888 total
includes taxes & fees
Aug 31 - Sep 1
River View Lodge - Hot Tub and Tastings Included
A wooden interior with a dining area, a bench, and a mirror on the wall.

3. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (22 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is ￥21,377
￥76,962 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Riverfront Cabin - Beach Access & Wood Stove
A patio with outdoor seating, a hot tub, and string lights.

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.
The price is ￥103,000
￥211,143 total
includes taxes & fees
Aug 31 - Sep 1
Healdsburg Plaza Gem-Hot Tub and Tastings Included

5. 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 ￥25,750
￥68,695 total
includes taxes & fees
Sep 2 - Sep 3
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

6. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ￥26,227
￥57,953 total
includes taxes & fees
Aug 24 - Aug 25
Wine Country Cottage Escape
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

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, (75 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is ￥41,327
￥91,714 total
includes taxes & fees
Aug 24 - Aug 25
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

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.
The price is ￥34,492
￥85,099 total
includes taxes & fees
Aug 25 - Aug 26
Russian River Brew-cation Home
A covered outdoor seating area with two sofas and a wooden table, surrounded by plants and a rustic setting.

9. Healdsburg Homestead with Pool, Hot Tub and Tastings Included

Healdsburg Homestead with Pool, Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (20 reviews)
"Amazing, beautiful property. "
United States
Michael M.
The price is ￥233,294
￥382,473 total
includes taxes & fees
Sep 8 - Sep 9
Healdsburg Homestead with Pool, Hot Tub and Tastings Included

10. The Grove on Alexander Valley

The Grove on Alexander Valley
Healdsburg
The price is ￥178,189
￥328,553 total
includes taxes & fees
Aug 27 - Aug 28
The Grove on Alexander Valley
A house with a swimming pool, outdoor furniture, and a well-maintained garden.

11. 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.
The price is ￥188,489
￥330,260 total
includes taxes & fees
Sep 14 - Sep 15
Eastside Eden - Pool, Hot Tub and Tastings Included
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

12. 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 ￥200,706
￥320,796 total
includes taxes & fees
Aug 24 - Aug 25
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

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 ￥105,066
￥203,860 total
includes taxes & fees
Sep 13 - Sep 14
Elegant Vineyard Living at a Private Wine Country Estate
A two-story house with a swimming pool, outdoor seating, and a staircase leading to the upper level.

14. 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 ￥86,453
￥165,335 total
includes taxes & fees
Sep 7 - Sep 8
Farpoint: Heated Infinity Pool, Mountain Views
A house surrounded by a fenced yard with a gravel driveway and a small patio.

15. 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 ￥150,894
￥278,025 total
includes taxes & fees
Sep 10 - Sep 11
Santini Farmhouse - Wine Tastings Included
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

16. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (74 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is ￥39,579
￥80,092 total
includes taxes & fees
Aug 24 - Aug 25
Wine Country Farmhouse with Hot Tub
A deck with outdoor seating, a grill, and a view of a house with large windows.

17. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (36 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is ￥30,042
￥79,965 total
includes taxes & fees
Aug 31 - Sep 1
Somms Rest ⎮ Designed. Curated. Peaceful.
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

18. 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 ￥28,611
￥83,544 total
includes taxes & fees
Aug 30 - Aug 31
Serenity at the Russian River
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

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, (13 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is ￥31,790
￥68,190 total
includes taxes & fees
Aug 25 - Aug 26
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

20. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Great place, would stay again!"
United States
Rachel S.
The price is ￥31,472
￥89,927 total
includes taxes & fees
Aug 24 - Aug 25
Wine Country Getaway
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
"Pet friendly, very friendly staffs"
Jamie 2-night trip
Posted 6 hours ago
Appellation Healdsburg

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
594
Accommodation
229 Vacation Homes
Lowest Price
￥57,953
Highest Price
￥382,473

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