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

Holiday Homes in Windsor

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Our top choices for Windsor holiday homes

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 €829
includes taxes & fees
8 Nov - 9 Nov
Sauna, Cold Plunge & Fire Pit Near Wineries

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 €875
includes taxes & fees
8 Nov - 9 Nov
Elegant Vineyard Living at a Private Wine Country Estate

3. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 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 €340
includes taxes & fees
2 Dec - 3 Dec
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

4. 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 €314
includes taxes & fees
9 Nov - 10 Nov
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

5. 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 €318
includes taxes & fees
9 Nov - 10 Nov
Wine Country Cottage Escape

6. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (22 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
United States
Greg K.
The price is €382
includes taxes & fees
8 Nov - 9 Nov
2BR Bungalow - Russian River & Wine Country

7. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (44 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 €461
includes taxes & fees
12 Nov - 13 Nov
Serenity at the Russian River

8. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is €351
includes taxes & fees
2 Dec - 3 Dec
Forestville Redwood Escape

9. 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 €362
includes taxes & fees
8 Dec - 9 Dec
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

10. 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 €424
includes taxes & fees
11 Nov - 12 Nov
Somms Rest ⎮ Designed. Curated. Peaceful.

11. 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)
"Great stay and location!"
United States
Brandi K.
The price is €276
includes taxes & fees
8 Nov - 9 Nov
Peaceful, charming, cottage in wine country. Beautiful yard!

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 €513
includes taxes & fees
22 Nov - 23 Nov
Russian River Brew-cation Home

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 €476
includes taxes & fees
8 Nov - 9 Nov
Wine Country Getaway

14. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 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 €245
includes taxes & fees
16 Nov - 17 Nov
2 Hidden Wine Country Gem Upstairs Unit

15. 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 €517
includes taxes & fees
9 Nov - 10 Nov
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

16. 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 €953
includes taxes & fees
17 Nov - 18 Nov
River View Lodge - Hot Tub and Tastings Included

17. 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, (16 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 €569
includes taxes & fees
18 Nov - 19 Nov
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!

18. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (30 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is €416
includes taxes & fees
8 Nov - 9 Nov
Cozy Riverfront Cabin - Beach Access & Wood Stove

19. Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (31 reviews)
"The location was perfect if you enjoy the Russian River Wineries and the Healdsburg area. The house itself is full of charm and character. It was nice to be able to unwind with friends at the dining table and play cards after a collaboratively cooked meal. The little town of Graton has a couple of good little restaurants, too!"
United States
Jeff D.
The price is €424
includes taxes & fees
9 Nov - 10 Nov
Relaxing Vineyard View, Rooftop Deck & Game Room

20. Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
Forestville
The price is €577
includes taxes & fees
16 Nov - 17 Nov
Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
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Top Windsor Hotel Reviews

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
510
Accommodation
845 Holiday Homes
Lowest Price
€245
Highest Price
€953