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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windsor vacation rentals

Room

1. 2 Separate 3BR Apts with Resort Amenities

2 Separate 3BR Apts with Resort Amenities
Windsor
2 Separate 3BR Apts with Resort Amenities
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 AED 1,837
AED 3,956 total
includes taxes & fees
13 Oct - 14 Oct
Elegant Vineyard Living at a Private Wine Country Estate
A hotel room with a dining table, chairs, a sofa, a coffee table, and a large window.

3. Professionally managed 3BR Condo, Pool, Fireplace, BBQ

Professionally managed 3BR Condo, Pool, Fireplace, BBQ
Windsor
The price is AED 4,823
AED 5,374 total
includes taxes & fees
10 Oct - 11 Oct
Professionally managed 3BR Condo, Pool, Fireplace, BBQ
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

4. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (134 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is AED 325
AED 370 total
includes taxes & fees
8 Nov - 9 Nov
Wildhaven Sonoma Glamping
Private kitchen

5. 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 AED 426
AED 1,373 total
includes taxes & fees
13 Oct - 14 Oct
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

6. 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 AED 900
AED 1,808 total
includes taxes & fees
29 Oct - 30 Oct
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

7. 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 AED 591
AED 1,553 total
includes taxes & fees
1 Nov - 2 Nov
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

8. 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.
The price is AED 556
AED 1,601 total
includes taxes & fees
12 Oct - 13 Oct
2BR Bungalow - Russian River & Wine Country
A bedroom with a bed, pillows, a blanket, and a painting on the wall.

9. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is AED 749
AED 1,715 total
includes taxes & fees
5 Nov - 6 Nov
Forestville Redwood Escape
A deck with outdoor seating, a grill, and a view of a house with large windows.

10. 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 AED 694
AED 1,874 total
includes taxes & fees
14 Oct - 15 Oct
Somms Rest ⎮ Designed. Curated. Peaceful.
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 AED 579
AED 1,319 total
includes taxes & fees
15 Oct - 16 Oct
Peaceful, charming, cottage in wine country. Beautiful yard!
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

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 AED 742
AED 1,885 total
includes taxes & fees
12 Oct - 13 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.

13. 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 AED 661
AED 1,986 total
includes taxes & fees
12 Oct - 13 Oct
Serenity at the Russian River
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

14. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.8 out of 10, Exceptional, (6 reviews)
"Nice camping spot "
United States
Evelyn
The price is AED 291
AED 332 total
includes taxes & fees
9 Oct - 10 Oct
The Ranch at Lake Sonoma
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

15. 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 AED 727
AED 2,067 total
includes taxes & fees
12 Oct - 13 Oct
Wine Country Getaway
A swimming pool with a slide, a barbecue area, and a wooden deck.

16. 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 AED 459
AED 1,032 total
includes taxes & fees
12 Oct - 13 Oct
2 Hidden Wine Country Gem Upstairs Unit
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

17. 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 AED 1,062
AED 2,171 total
includes taxes & fees
19 Oct - 20 Oct
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A wooden interior with a dining area, a bench, and a mirror on the wall.

18. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (26 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is AED 986
AED 2,362 total
includes taxes & fees
16 Oct - 17 Oct
Cozy Riverfront Cabin - Beach Access & Wood Stove
A deck with red Adirondack chairs, a fire pit, and a wooden staircase leading to a house.

19. Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (13 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is AED 555
AED 1,276 total
includes taxes & fees
12 Oct - 13 Oct
Tranquil Redwood Retreat
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
"Still waiting on deposit back but great hotel"
Vincent 1-night trip
Posted 7 hours ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Powell's Sweet Shoppe - Windsor, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Windsor has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: Visitors like this Windsor vacation home rental. It is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

Choose from 30 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Cultural attractions include Pacific Coast Air Museum, whereas Russian River is a spot to enjoy nature. Windsor Golf Club and Windsor Oaks Vineyards are other places to visit while you're in town.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.