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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor holiday homes

Property grounds

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.
Wildflower
Outdoor pool, a heated pool

2. Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Healdsburg
9.6 out of 10, Exceptional, (193 reviews)
"Great location and cozy home."
United States
Kelly B.
The price is €845
includes taxes & fees
28 Sept - 29 Sept
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Dining

3. 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.
Elegant Vineyard Living at a Private Wine Country Estate
Pool

4. 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.
Eastside Eden - Pool, Hot Tub and Tastings Included
Terrace/patio

5. 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.
The price is €347
includes taxes & fees
23 Sept - 24 Sept
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Coffee/tea maker, fridge, microwave, oven

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 €378
includes taxes & fees
21 Oct - 22 Oct
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

7. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is €323
includes taxes & fees
28 Sept - 29 Sept
Wine Country Cottage Escape
Smart TV

8. 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 €474
includes taxes & fees
27 Sept - 28 Sept
Serenity at the Russian River
Terrace/patio

9. 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 €433
includes taxes & fees
14 Oct - 15 Oct
Somms Rest ⎮ Designed. Curated. Peaceful.
Outdoor dining

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 €299
includes taxes & fees
28 Sept - 29 Sept
Peaceful, charming, cottage in wine country. Beautiful yard!
Dining

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 €471
includes taxes & fees
22 Oct - 23 Oct
Wine Country Getaway
Outdoor pool

12. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (30 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 €235
includes taxes & fees
4 Oct - 5 Oct
2 Hidden Wine Country Gem Upstairs Unit
Outdoor dining

13. 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 €473
includes taxes & fees
27 Sept - 28 Sept
Russian River Brew-cation Home
Dining

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, (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 €368
includes taxes & fees
18 Oct - 19 Oct
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Dining

15. 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 €452
includes taxes & fees
5 Oct - 6 Oct
Cozy Riverfront Cabin - Beach Access & Wood Stove
Smart TV, fireplace, stereo

16. 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, (20 reviews)
"Loved this place. Everything was labeled making the house easy to find things."
United States
Joel B.
Charming Wine Country Home w/Hot Tub near Downtown
Property grounds

17. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (53 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
The price is €433
includes taxes & fees
23 Sept - 24 Sept
Private Lofted Downtown Studio
Sun-loungers, beach towels

18. Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country

Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country
Sebastopol
9.8 out of 10, Exceptional, (72 reviews)
"Loved this place. Rustic but in the best way. Property was nice. Would stay there again."
United States
Stephen F.
The price is €435
includes taxes & fees
28 Sept - 29 Sept
Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country
3 bedrooms, iron/ironing board, free WiFi, bed sheets

19. Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun

Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun
Southwest Santa Rosa
9.8 out of 10, Exceptional, (63 reviews)
"Very cute and clean house, central location. Kitchen stocked well. Would stay again. "
United States
Michelle C.
The price is €511
includes taxes & fees
23 Sept - 24 Sept
Sonoma Wine Country Retreat | Hot Tub, BBQ & Mini Golf Fun
Interior

20. Walk to Downtown Sebastopol * Luxe Vacation Studio

Walk to Downtown Sebastopol * Luxe Vacation Studio
Sebastopol
8.4 out of 10, Very good, (7 reviews)
"This is a cute property nestled at the top of the drive in a wooded neighborhood. The outdoor niche would be a pleasant spot for reading. It has a cozy roominess with tidy appointments. It's an easy drive to the Sebastopol business district, which has a wonderful, rustic quirkiness. We highly recommend a drive to Goat Rock on the coast, then to Armstrong Redwood Reserve, and lunch at Baked on the River in Guerneville."
United States
Steven M.
Walk to Downtown Sebastopol * Luxe Vacation Studio
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

Calistoga Motor Lodge and Spa

Calistoga Motor Lodge and Spa

10/10 Excellent
"Wanted coffee but didn't want to sit and read directions on how to prepare a cup in my room. Had to go to office to find where breakfast was being served to buy coffee. I expected to see a small coffee area where it was already prepared. Breakfast was good. Surprised that I had to pay for breakfast as I thought it would be included with the price I had paid for the room."
Jo 2-night trip
Posted 1 hour ago
Calistoga Motor Lodge and Spa

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
12,192
Accommodation
1061 Holiday Homes
Lowest Price
€73
Highest Price
€311