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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Windsor holiday homes

A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

1. 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 £821
includes taxes & fees
26 Oct - 27 Oct
Elegant Vineyard Living at a Private Wine Country Estate
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

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)
"Great location!"
United States
Riley F.
The price is £373
includes taxes & fees
29 Oct - 30 Oct
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Private kitchen

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 £286
includes taxes & fees
21 Oct - 22 Oct
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

4. 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 £318
includes taxes & fees
10 Nov - 11 Nov
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A bedroom with a bed, pillows, a blanket, and a painting on the wall.

5. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is £327
includes taxes & fees
2 Nov - 3 Nov
Forestville Redwood Escape
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

6. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (20 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
United States
Greg K.
2BR Bungalow - Russian River & Wine Country
A deck with outdoor seating, a grill, and a view of a house with large windows.

7. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (37 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is £397
includes taxes & fees
1 Nov - 2 Nov
Somms Rest ⎮ Designed. Curated. Peaceful.
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 £381
includes taxes & fees
19 Oct - 20 Oct
Russian River Brew-cation Home
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)
"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 £401
includes taxes & fees
19 Oct - 20 Oct
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 £287
includes taxes & fees
9 Nov - 10 Nov
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)
The price is £419
includes taxes & fees
15 Oct - 16 Oct
Wine Country Getaway
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

12. 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 £472
includes taxes & fees
26 Oct - 27 Oct
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

13. 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 £433
includes taxes & fees
15 Oct - 16 Oct
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
A swimming pool with a slide, a barbecue area, and a wooden deck.

14. 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 £218
includes taxes & fees
15 Oct - 16 Oct
2 Hidden Wine Country Gem Upstairs Unit
A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

15. ❤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 price is £394
includes taxes & fees
21 Oct - 22 Oct
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
A modern kitchen with a central island, bar stools, and a dining table set with candles.

16. 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, (14 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.
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
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, (27 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is £438
includes taxes & fees
16 Oct - 17 Oct
Cozy Riverfront Cabin - Beach Access & Wood Stove
A bedroom with a bed, a nightstand, a lamp, and a framed picture on the wall.

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 £768
includes taxes & fees
19 Oct - 20 Oct
Farpoint: Heated Infinity Pool, Mountain Views
A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a hanging pot rack.

19. Charming Dog-Friendly Home Near Regional Park

Charming Dog-Friendly Home Near Regional Park
Sebastopol
10.0 out of 10, Exceptional, (33 reviews)
"Great place to stay"
United States
Michelle D.
Charming Dog-Friendly Home Near Regional Park
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

10/10 Excellent
"A great stay!"
Jordan 1-night trip
Posted 2 hours ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
565
Accommodation
1054 Holiday Homes
Lowest Price
£218
Highest Price
£821