A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windsor 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 ￥27,346
￥138,547 total
includes taxes & fees
Sep 9 - Sep 10
Wildflower
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

2. 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 ￥80,943
￥171,186 total
includes taxes & fees
Sep 8 - Sep 9
Elegant Vineyard Living at a Private Wine Country Estate
A house with a swimming pool, outdoor furniture, and a well-maintained garden.

3. 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 ￥197,703
￥348,308 total
includes taxes & fees
Sep 14 - Sep 15
Eastside Eden - Pool, Hot Tub and Tastings Included
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

4. 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
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

5. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ￥25,783
￥57,285 total
includes taxes & fees
Sep 8 - Sep 9
Wine Country Cottage Escape

6. 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 ￥23,908
￥64,992 total
includes taxes & fees
Sep 16 - Sep 17
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A spacious living area with a high ceiling, a large window, and a cozy seating arrangement.

7. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is ￥20,783
￥61,254 total
includes taxes & fees
Sep 28 - Sep 29
Forestville Redwood Escape
A deck with outdoor seating, a grill, and a view of a house with large windows.

8. 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 ￥29,533
￥79,705 total
includes taxes & fees
Sep 15 - Sep 16
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.

9. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts. Very accommodating. Clean and beautiful property. Great timely communication with hosts."
United States
Neeraj
The price is ￥28,127
￥82,287 total
includes taxes & fees
Sep 8 - Sep 9
Serenity at the Russian River
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

10. Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, charming cottage in a quiet neighborhood. Close to wineries and food."
United States
Mikaela
The price is ￥22,501
￥53,422 total
includes taxes & fees
Sep 8 - Sep 9
Peaceful, charming, cottage in wine country. Beautiful yard!
A swimming pool with a slide, a barbecue area, and a wooden deck.

11. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (28 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is ￥18,282
￥41,984 total
includes taxes & fees
Sep 13 - Sep 14
2 Hidden Wine Country Gem Upstairs Unit
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

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 ￥31,408
￥79,402 total
includes taxes & fees
Sep 8 - Sep 9
Russian River Brew-cation Home
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

13. 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 ￥30,939
￥84,811 total
includes taxes & fees
Sep 8 - Sep 9
Wine Country Getaway
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

14. 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, (14 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is ￥33,752
￥71,398 total
includes taxes & fees
Sep 14 - Sep 15
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

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, (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.
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

16. 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 ￥53,910
￥105,929 total
includes taxes & fees
Sep 8 - Sep 9
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A wooden interior with a dining area, a bench, and a mirror on the wall.

17. 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 ￥28,511
￥84,199 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Riverfront Cabin - Beach Access & Wood Stove
A living room with a wooden dining table set for four, a black sofa, and a small coffee table.

18. Charming Wine Country Home w/Hot Tub near Downtown

Charming Wine Country Home w/Hot Tub near Downtown
Santa Rosa
9.6 out of 10, Exceptional, (19 reviews)
"Great place to stay! Everything was clean and comfortable, and the location was perfect. The host was easy to communicate with and made the process simple. Would definitely stay here again."
United States
Steve S.
The price is ￥29,814
￥77,897 total
includes taxes & fees
Sep 15 - Sep 16
Charming Wine Country Home w/Hot Tub near Downtown
A spacious living area with a wooden ceiling, a sofa, a coffee table, and a kitchen in the background.

19. Walk to Downtown Sebastopol * Luxe Vacation Living

Walk to Downtown Sebastopol * Luxe Vacation Living
Sebastopol
9.6 out of 10, Exceptional, (9 reviews)
"Lovely home with a view. Great amenities. Very convenient with quick walk to the downtown. We would definitely stay there again!"
United States
Courtney E.
The price is ￥32,158
￥59,613 total
includes taxes & fees
Sep 16 - Sep 17
Walk to Downtown Sebastopol * Luxe Vacation Living
A two-story house with a swimming pool, outdoor seating, and a staircase leading to the upper level.

20. 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 ￥76,458
￥153,763 total
includes taxes & fees
Sep 8 - Sep 9
Farpoint: Heated Infinity Pool, Mountain Views
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 Windsor Hotel Reviews

DoubleTree by Hilton Sonoma - Wine Country

DoubleTree by Hilton Sonoma - Wine Country

10/10 Excellent
"Love the cookies"
Martha 1-night trip
Posted 3 hours ago
DoubleTree by Hilton Sonoma - Wine Country

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
10,320
Accommodation
1061 Vacation Homes
Lowest Price
￥13,751
Highest Price
￥32,202