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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windsor vacation rentals

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

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 ￥41,546
￥159,753 total
includes taxes & fees
Oct 27 - Oct 28
Wildflower
A swimming pool with lounge chairs and an umbrella, surrounded by a grassy area and trees.

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.
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

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.
The price is ￥81,518
￥172,245 total
includes taxes & fees
Oct 27 - Oct 28
Elegant Vineyard Living at a Private Wine Country Estate
Room

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

Professionally managed 3BR Condo, Pool, Fireplace, BBQ
Windsor
The price is ￥177,109
￥196,158 total
includes taxes & fees
Oct 31 - Nov 1
Professionally managed 3BR Condo, Pool, Fireplace, BBQ
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

5. 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 ￥13,775
￥15,703 total
includes taxes & fees
Nov 1 - Nov 2
Wildhaven Sonoma Glamping
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 ￥36,209
￥74,540 total
includes taxes & fees
Oct 25 - Oct 26
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A bedroom with a bed, pillows, a blanket, and a painting on the wall.

7. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is ￥27,068
￥68,771 total
includes taxes & fees
Oct 6 - Oct 7
Forestville Redwood Escape
Private kitchen

8. 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 ￥18,419
￥58,860 total
includes taxes & fees
Oct 14 - Oct 15
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

9. 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 ￥23,836
￥68,151 total
includes taxes & fees
Oct 13 - Oct 14
2BR Bungalow - Russian River & Wine Country
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, (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 ￥28,327
￥84,445 total
includes taxes & fees
Oct 4 - Oct 5
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 ￥25,189
￥56,958 total
includes taxes & fees
Nov 1 - Nov 2
Peaceful, charming, cottage in wine country. Beautiful yard!
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

12. 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 ￥31,159
￥87,932 total
includes taxes & fees
Oct 4 - Oct 5
Wine Country Getaway
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

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 ￥31,631
￥80,280 total
includes taxes & fees
Oct 5 - Oct 6
Russian River Brew-cation Home
A deck with outdoor seating, a grill, and a view of a house with large windows.

14. 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 ￥29,754
￥80,302 total
includes taxes & fees
Nov 1 - Nov 2
Somms Rest ⎮ Designed. Curated. Peaceful.
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

15. 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 ￥23,606
￥64,617 total
includes taxes & fees
Oct 26 - Oct 27
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A hot tub on a wooden deck with a view of a forested area.

16. Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.4 out of 10, Exceptional, (10 reviews)
"Very unique and charming property. Definitely felt like being in a tree house in the redwoods. We spent most of our time when there sitting on the deck. It was conveniently located to everything we wanted to do - drive to the coast, hike at the state park, and visit nearby restaurants and wineries."
United States
Sherri
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A white building with a black balcony, surrounded by lush greenery and trees.

17. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.2 out of 10, Wonderful, (7 reviews)
"Beautiful place. Bed was extremely comfortable. Overall environment was pleasant. Coffee set up was good for me as a black coffee drinker. We would stay again and would happily recommend it to others."
United States
Brad
The price is ￥23,803
￥43,032 total
includes taxes & fees
Oct 27 - Oct 28
Sebastopol Lux Walk toTown Guest Suite
A swimming pool with a slide, a barbecue area, and a wooden deck.

18. 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 ￥18,412
￥42,439 total
includes taxes & fees
Oct 4 - Oct 5
2 Hidden Wine Country Gem Upstairs Unit
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

19. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (80 reviews)
"Lovely vacation rental"
United States
suzanne g.
The price is ￥31,474
￥66,253 total
includes taxes & fees
Oct 7 - Oct 8
Wine Country Cottage in downtown Santa Rosa, CA
A living room with a wooden dining table set for four, a black sofa, and a small coffee table.

20. 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 ￥30,026
￥78,293 total
includes taxes & fees
Oct 5 - Oct 6
Charming Wine Country Home w/Hot Tub near Downtown
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

La Quinta Inn & Suites Santa Rosa Sonoma

La Quinta Inn & Suites Santa Rosa Sonoma

10/10 Excellent
"Great staff, clean rooms, comfortable beds and good coffee/breakfast"
Terrence 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites Santa Rosa Sonoma

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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.