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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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Windsor holiday 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 AU$1,344
includes taxes & fees
1 Nov - 2 Nov
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 AU$1,652
includes taxes & fees
2 Nov - 3 Nov
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 AU$621
includes taxes & fees
16 Nov - 17 Nov
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Private kitchen

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 AU$488
includes taxes & fees
1 Nov - 2 Nov
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

5. 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 AU$556
includes taxes & fees
22 Nov - 23 Nov
2BR Bungalow - Russian River & Wine Country
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

6. 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 AU$609
includes taxes & fees
3 Nov - 4 Nov
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A wooden structure with a circular entrance, a small table, and a sofa outside a house.

7. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is AU$534
includes taxes & fees
16 Nov - 17 Nov
Forestville Redwood Escape
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.
Russian River Brew-cation Home
A deck with outdoor seating, a grill, and a view of a house with large windows.

9. 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 AU$694
includes taxes & fees
5 Nov - 6 Nov
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.

10. 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 AU$726
includes taxes & fees
1 Nov - 2 Nov
Serenity at the Russian River
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

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)
"Beautiful, charming cottage in a quiet neighborhood. Close to wineries and food."
United States
Mikaela
The price is AU$518
includes taxes & fees
30 Nov - 1 Dec
Peaceful, charming, cottage in wine country. Beautiful yard!
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, (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 AU$406
includes taxes & fees
17 Nov - 18 Nov
2 Hidden Wine Country Gem Upstairs Unit
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 AU$756
includes taxes & fees
1 Nov - 2 Nov
Wine Country Getaway
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

14. 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 AU$1,196
includes taxes & fees
12 Nov - 13 Nov
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A modern kitchen with a central island, bar stools, and a dining table set with candles.

15. 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 AU$736
includes taxes & fees
2 Nov - 3 Nov
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.

16. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (29 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is AU$670
includes taxes & fees
1 Nov - 2 Nov
Cozy Riverfront Cabin - Beach Access & Wood Stove
A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

17. 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, (85 reviews)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
An outdoor patio with a wooden table and chairs, a grill, and string lights.

18. Moonlit Manor-walk to Steelhead Beach + the market

Moonlit Manor-walk to Steelhead Beach + the market
Forestville
The price is AU$1,058
includes taxes & fees
3 Nov - 4 Nov
Moonlit Manor-walk to Steelhead Beach + the market
A staircase with a patterned carpet and a white railing leading to a landing.

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

Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
Forestville
The price is AU$902
includes taxes & fees
2 Nov - 3 Nov
Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
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, (40 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 AU$2,237
includes taxes & fees
3 Nov - 4 Nov
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

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"😊"
Theresa 2-night trip
Posted 6 hours ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
480
Accommodation
1005 Holiday Homes
Lowest Price
AU$406
Highest Price
AU$2,237