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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Windsor vacation homes

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

1. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
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 ￥46,693
￥176,652 total
includes taxes & fees
Oct 26 - Oct 27
Sauna, Cold Plunge & Fire Pit Near Wineries
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 ￥79,085
￥172,405 total
includes taxes & fees
Oct 26 - Oct 27
Elegant Vineyard Living at a Private Wine Country Estate
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

3. 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)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is ￥28,490
￥64,970 total
includes taxes & fees
Oct 29 - Oct 30
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.

4. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
United States
Tina A.
The price is ￥26,098
￥58,143 total
includes taxes & fees
Nov 18 - Nov 19
Wine Country Cottage Escape
Private kitchen

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 ￥18,348
￥59,115 total
includes taxes & fees
Nov 4 - Nov 5
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A modern kitchen with white cabinets, a microwave, a stove, and a washing machine.

6. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is ￥29,598
￥71,859 total
includes taxes & fees
Nov 11 - Nov 12
Forestville Redwood Escape
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

7. 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, (15 reviews)
"Nice place, great location, had everything we needed. Helpful and prompt communication by the host. This was a great base for exploring the area."
United States
Rebecca I.
The price is ￥25,307
￥67,507 total
includes taxes & fees
Nov 4 - Nov 5
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
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, (38 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is ￥29,894
￥79,098 total
includes taxes & fees
Nov 4 - Nov 5
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, (43 reviews)
"We had a great stay. The house was clean, the beds were comfy and a very convenient location. Just wish there was an ironing board. I would definitely recommend staying here."
United States
Patricia A.
The price is ￥28,471
￥85,507 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥22,792
￥54,112 total
includes taxes & fees
Nov 2 - Nov 3
Peaceful, charming, cottage in wine country. Beautiful yard!
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

11. 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 ￥31,318
￥89,170 total
includes taxes & fees
Oct 29 - Oct 30
Wine Country Getaway
A swimming pool with a slide, a barbecue area, and a wooden deck.

12. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (31 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 ￥19,787
￥44,431 total
includes taxes & fees
Oct 29 - Oct 30
2 Hidden Wine Country Gem Upstairs Unit
A wooden interior with a dining area, a bench, and a mirror on the wall.

13. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (28 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is ￥20,371
￥73,713 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Riverfront Cabin - Beach Access & Wood Stove
A modern kitchen with a central island, bar stools, and a dining table set with candles.

14. Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!

Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"We had an excellent stay and will definitely keep this place in mind for future stays. The rooms were spacious and everything was well appointed. We enjoyed the hot tub and the swings on the front porch. An overall great place. "
United States
Emily N.
The price is ￥41,702
￥91,310 total
includes taxes & fees
Nov 4 - Nov 5
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
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)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
The price is ￥35,455
￥84,626 total
includes taxes & fees
Oct 26 - Oct 27
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, (76 reviews)
"Our stay was very comfortable."
United States
Kim R.
The price is ￥45,585
￥96,538 total
includes taxes & fees
Oct 26 - Oct 27
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

17. 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
A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

18. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Healdsburg
10.0 out of 10, Exceptional, (15 reviews)
"Awesome stay. Highly recommended"
United States
sharon p.
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

19. 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)
"Wonderful vacation and location. "
United States
Leslie M.
The price is ￥78,152
￥180,510 total
includes taxes & fees
Nov 3 - Nov 4
River View Lodge - Hot Tub and Tastings Included
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

20. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (39 reviews)
"Stayed here on a couples trip to Napa and Sonoma. It was a perfect home base for the trip, had everything we needed and the two masters suites were almost identical which was a nice bonus so both couples felt equally comfortable."
United States
Chris N.
The price is ￥137,598
￥261,274 total
includes taxes & fees
Nov 3 - Nov 4
Vineyard Vue - Wine 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 Windsor Hotel Reviews

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

8/10 Good
"The establishment was clean and neat enough. The overall feel was of an older "Las Vegas" hotel. Staff was helpful when I needed them. The room and linens were clean, but there was an ant problem. Hot tub was clean and functional. Breakfast was in cramped quarters but decent fare."
Cathy 3-night trip
Posted 11 hours ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
512
Accommodation
1061 Vacation Homes
Lowest Price
￥44,431
Highest Price
￥261,274