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

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Windsor holiday rentals

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

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 HK$1,671
HK$7,807 total
includes taxes & fees
1 Nov - 2 Nov
Sauna, Cold Plunge & Fire Pit Near Wineries
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 HK$3,922
HK$8,449 total
includes taxes & fees
2 Nov - 3 Nov
Elegant Vineyard Living at a Private Wine Country Estate
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

3. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (138 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is HK$769
HK$876 total
includes taxes & fees
29 Nov - 30 Nov
Wildhaven Sonoma Glamping
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

4. 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 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 HK$1,608
HK$3,463 total
includes taxes & fees
16 Nov - 17 Nov
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
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 HK$816
HK$2,777 total
includes taxes & fees
3 Nov - 4 Nov
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

6. 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 HK$1,153
HK$3,189 total
includes taxes & fees
22 Nov - 23 Nov
2BR Bungalow - Russian River & Wine Country
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 HK$1,412
HK$3,547 total
includes taxes & fees
2 Nov - 3 Nov
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A wooden structure with a circular entrance, a small table, and a sofa outside a house.

8. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is HK$1,263
HK$3,311 total
includes taxes & fees
16 Nov - 17 Nov
Forestville Redwood Escape
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

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 HK$1,306
HK$2,903 total
includes taxes & fees
9 Nov - 10 Nov
Peaceful, charming, cottage in wine country. Beautiful yard!
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, (38 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is HK$1,483
HK$4,033 total
includes taxes & fees
2 Nov - 3 Nov
Somms Rest ⎮ Designed. Curated. Peaceful.
A hot tub on a wooden deck with a view of a forested area.

11. 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
The price is HK$1,173
HK$3,530 total
includes taxes & fees
1 Nov - 2 Nov
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

12. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (43 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 HK$1,412
HK$4,209 total
includes taxes & fees
1 Nov - 2 Nov
Serenity at the Russian River
A wooden interior with a dining area, a bench, and a mirror on the wall.

13. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (29 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is HK$1,101
HK$3,884 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Riverfront Cabin - Beach Access & Wood Stove
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
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
The price is HK$621
HK$708 total
includes taxes & fees
30 Oct - 31 Oct
The Ranch at Lake Sonoma
A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

15. 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 HK$1,586
HK$4,453 total
includes taxes & fees
2 Nov - 3 Nov
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

16. 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 patio area with a stone floor, outdoor seating, and a house in the background.

17. 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 HK$988
HK$1,852 total
includes taxes & fees
3 Nov - 4 Nov
Sebastopol Lux Walk toTown Guest Suite
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

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 HK$1,553
HK$4,391 total
includes taxes & fees
2 Nov - 3 Nov
Wine Country Getaway
A swimming pool with a slide, a barbecue area, and a wooden deck.

19. 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 HK$1,090
HK$2,328 total
includes taxes & fees
17 Nov - 18 Nov
2 Hidden Wine Country Gem Upstairs Unit
A modern kitchen with a central island, bar stools, and a dining table set with candles.

20. Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!

Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"We had an excellent stay and will definitely keep this place in mind for future stays. The rooms were spacious and everything was well appointed. We enjoyed the hot tub and the swings on the front porch. An overall great place. "
United States
Emily N.
Modern Luxury Home by Russian River - Private Hot Tub, Office, EV Charger, Deck!
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 Inn at the Tides

The Inn at the Tides

10/10 Excellent
"We got to check in early and had an amazing clean room. Checked out the jacuzzi that’s open till 11pm! Such a great stay will be back again"
Brooke 1-night trip
Posted 6 hours ago
The Inn at the Tides

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 holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Powell's Sweet Shoppe - Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 are some of the best holiday rentals that Windsor has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This holiday home rental outside of Windsor 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 holiday rentals are there in Windsor?

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

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 holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.