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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Our top choices for Windsor vacation rentals

1. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
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 CA $301
CA $1,323 total
includes taxes & fees
Nov 9 - Nov 10
Sauna, Cold Plunge & Fire Pit Near Wineries

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 CA $500
CA $1,390 total
includes taxes & fees
Nov 10 - Nov 11
Elegant Vineyard Living at a Private Wine Country Estate

3. Tuscan by Onalani 2x3BR Year-round pools & hot tubs

Tuscan by Onalani 2x3BR Year-round pools & hot tubs
Windsor
The price is CA $6,940
CA $7,390 total
includes taxes & fees
Nov 28 - Nov 29
Tuscan by Onalani 2x3BR Year-round pools & hot tubs

4. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (139 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is CA $129
CA $147 total
includes taxes & fees
Dec 9 - Dec 10
Wildhaven Sonoma Glamping

5. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is CA $242
CA $544 total
includes taxes & fees
Dec 2 - Dec 3
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

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 CA $153
CA $490 total
includes taxes & fees
Nov 10 - Nov 11
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

7. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (22 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
United States
Greg K.
The price is CA $210
CA $597 total
includes taxes & fees
Nov 9 - Nov 10
2BR Bungalow - Russian River & Wine Country

8. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (44 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 CA $254
CA $731 total
includes taxes & fees
Nov 12 - Nov 13
Serenity at the Russian River

9. 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, (16 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 CA $227
CA $557 total
includes taxes & fees
Nov 17 - Nov 18
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

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)
"Great stay and location!"
United States
Brandi K.
The price is CA $200
CA $462 total
includes taxes & fees
Nov 19 - Nov 20
Peaceful, charming, cottage in wine country. Beautiful yard!

11. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
The price is CA $112
CA $128 total
includes taxes & fees
Nov 9 - Nov 10
The Ranch at Lake Sonoma

12. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (38 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is CA $267
CA $695 total
includes taxes & fees
Nov 18 - Nov 19
Somms Rest ⎮ Designed. Curated. Peaceful.

13. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
4.0 out of 10, (1 review)
"Old but quaint. No amenities, no updates. Coffee cups looked like thrift shop purchases. Bed was comfortable. Bath shower drained poorly. Too expensive for a 2 star property."
United States
Chris
The price is CA $311
CA $357 total
includes taxes & fees
Nov 17 - Nov 18
Hideaway Cottages

14. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 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 CA $177
CA $381 total
includes taxes & fees
Nov 16 - Nov 17
2 Hidden Wine Country Gem Upstairs Unit

15. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.4 out of 10, Exceptional, (8 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 CA $178
CA $331 total
includes taxes & fees
Nov 16 - Nov 17
Sebastopol Lux Walk toTown Guest Suite

16. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (30 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is CA $179
CA $651 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Riverfront Cabin - Beach Access & Wood Stove

17. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
10.0 out of 10, Exceptional, (10 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
The price is CA $258
CA $721 total
includes taxes & fees
Nov 9 - Nov 10
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

18. 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 CA $280
CA $761 total
includes taxes & fees
Nov 9 - Nov 10
Wine Country Getaway

19. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (67 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
The price is CA $156
CA $287 total
includes taxes & fees
Nov 12 - Nov 13
The Tiny Tipsy Turtle

20. 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 CA $339
CA $761 total
includes taxes & fees
Nov 22 - Nov 23
Russian River Brew-cation Home
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

Find out more about Windsor

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.