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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 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.
The price is AU$1,258
includes taxes & fees
22 Sept - 23 Sept
Wildflower
Dining

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$1,515
includes taxes & fees
21 Sept - 22 Sept
Elegant Vineyard Living at a Private Wine Country Estate
Terrace/patio

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)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is AU$542
includes taxes & fees
21 Sept - 22 Sept
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Interior

4. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (19 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$604
includes taxes & fees
16 Sept - 17 Sept
2BR Bungalow - Russian River & Wine Country
Dining

5. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AU$517
includes taxes & fees
21 Sept - 22 Sept
Wine Country Cottage Escape
Private kitchen

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 AU$533
includes taxes & fees
20 Sept - 21 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Terrace/patio

7. 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 AU$716
includes taxes & fees
16 Sept - 17 Sept
Somms Rest ⎮ Designed. Curated. Peaceful.
Living area

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 AU$750
includes taxes & fees
16 Sept - 17 Sept
Serenity at the Russian River
Outdoor dining

9. 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$449
includes taxes & fees
28 Sept - 29 Sept
Peaceful, charming, cottage in wine country. Beautiful yard!
Dining

10. 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$781
includes taxes & fees
16 Sept - 17 Sept
Wine Country Getaway
Pool

11. 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 AU$375
includes taxes & fees
20 Sept - 21 Sept
2 Hidden Wine Country Gem Upstairs Unit
Dining

12. 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$608
includes taxes & fees
5 Oct - 6 Oct
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Games room

13. Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (27 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 AU$719
includes taxes & fees
16 Sept - 17 Sept
Relaxing Vineyard View, Rooftop Deck & Game Room
Dining

14. 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 AU$683
includes taxes & fees
16 Sept - 17 Sept
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor dining

15. 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 AU$740
includes taxes & fees
16 Sept - 17 Sept
Russian River Brew-cation Home
Terrace/patio

16. Charming Dog-Friendly Home Near Regional Park

Charming Dog-Friendly Home Near Regional Park
Sebastopol
10.0 out of 10, Exceptional, (31 reviews)
"Great place to stay"
United States
Michelle D.
The price is AU$511
includes taxes & fees
16 Sept - 17 Sept
Charming Dog-Friendly Home Near Regional Park
Living area

17. 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.
The price is AU$684
includes taxes & fees
16 Sept - 17 Sept
Charming Wine Country Home w/Hot Tub near Downtown
Living area

18. 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)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is AU$975
includes taxes & fees
22 Sept - 23 Sept
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Private kitchen

19. Modern Country Home | Near Downtown & Bike Trail

Modern Country Home | Near Downtown & Bike Trail
Sebastopol
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and lots of you nearby"
United States
Santo Q.
Modern Country Home | Near Downtown & Bike Trail
Pool

20. 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 AU$1,357
includes taxes & fees
30 Sept - 1 Oct
Farpoint: Heated Infinity Pool, Mountain Views
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

Hotel E

Hotel E

10/10 Excellent
"Good all around"
Russell 1-night trip
Posted 17 hours ago
Hotel E

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
476
Accommodation
1054 Holiday Homes
Lowest Price
AU$375
Highest Price
AU$1,515