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

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 ￥54,287
￥169,349 total
includes taxes & fees
Oct 13 - Oct 14
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.
The price is ￥83,092
￥153,680 total
includes taxes & fees
Sep 28 - Sep 29
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 ￥82,300
￥174,223 total
includes taxes & fees
Sep 28 - Sep 29
Elegant Vineyard Living at a Private Wine Country Estate
A house with a swimming pool, outdoor furniture, and a well-maintained garden.

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
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, (133 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is ￥14,487
￥16,516 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥27,064
￥61,472 total
includes taxes & fees
Sep 30 - Oct 1
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

7. 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 ￥18,518
￥58,700 total
includes taxes & fees
Sep 29 - Sep 30
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

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 ￥28,489
￥85,403 total
includes taxes & fees
Sep 27 - Sep 28
Serenity at the Russian River
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, (36 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is ￥29,913
￥80,730 total
includes taxes & fees
Oct 6 - Oct 7
Somms Rest ⎮ Designed. Curated. Peaceful.
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

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 ￥31,337
￥85,902 total
includes taxes & fees
Sep 28 - Sep 29
Wine Country Getaway
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

11. 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 spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

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 ￥27,781
￥70,898 total
includes taxes & fees
Sep 29 - Sep 30
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

13. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (79 reviews)
"Lovely vacation rental"
United States
suzanne g.
The price is ￥31,654
￥66,473 total
includes taxes & fees
Oct 1 - Oct 2
Wine Country Cottage in downtown Santa Rosa, CA
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

14. 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 ￥21,794
￥52,834 total
includes taxes & fees
Sep 28 - Sep 29
Peaceful, charming, cottage in wine country. Beautiful yard!
An entrance with a wooden door, a wicker chair, a cushioned bench, a window with a view of trees, and a hanging light fixture.

15. 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 ￥37,747
￥76,780 total
includes taxes & fees
Sep 27 - Sep 28
Private Lofted Downtown Studio
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

16. 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 ￥54,603
￥107,924 total
includes taxes & fees
Oct 7 - Oct 8
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A beach with a large rock formation, a sandy shore, and a calm sea.

17. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (66 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
The price is ￥16,302
￥32,186 total
includes taxes & fees
Sep 30 - Oct 1
The Tiny Tipsy Turtle
A wooden staircase leading to a building with a balcony, surrounded by trees.

18. Rivers Breeze - Wine Tastings Included

Rivers Breeze - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (20 reviews)
"Lovely place, exactly as described. Really nice place to sit & listen to nature, access to river, well-appointed, easy, and the owners are responsive and easy to work with."
United States
Seppo H.
Rivers Breeze - Wine Tastings Included
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

19. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful stay!"
United States
Adam C.
The price is ￥49,855
￥56,502 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Wine Country Guesthouse with Private Pool & Yard
A covered patio with a dining table, chairs, and a sofa.

20. Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (69 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
The price is ￥85,637
￥185,247 total
includes taxes & fees
Oct 6 - Oct 7
Redwood Riverfront - Hot Tub and 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

Oxford Suites Sonoma County

Oxford Suites Sonoma County

8/10 Good
"Room was large and well appointed. Bathroom was large with good counter space and lighting. Social hour was not worth bothering with. Cold pinot noir in plastic cup and restaurant food not particularly good. They did include a good breakfast buffet."
Alice 2-night trip
Posted 2 hours ago
Oxford Suites Sonoma County

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.