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Windsor Holiday Rentals

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Check prices for these dates

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Windsor holiday rentals

Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Holiday Home in Windsor

Private Vineyard Estate | Sleeps 10
9.6 out of 10, Exceptional, (4)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is HK$5,044
HK$9,542 total
includes taxes & fees
5 Jan - 6 Jan 2026
Private Vineyard Estate | Sleeps 10
Front of property
The Ranch at Lake Sonoma

Camping in Geyserville

The Ranch at Lake Sonoma
1.0 star property
10.0 out of 10, Exceptional, (2)
"Nice camping spot "
United States
Evelyn
The price is HK$462
HK$526 total
includes taxes & fees
29 Dec - 30 Dec
The Ranch at Lake Sonoma
Interior
Tranquil Redwood Retreat

Mobile Home in Guerneville

Tranquil Redwood Retreat
8.8 out of 10, Excellent, (10)
"We had a lovely stay at the Tranquil Redwood Retreat! The cabin was clean, cozy, and beautifully decorated—just like the photos. The kitchen was fully stocked with everything we needed, and the check-in process was smooth and easy. It was the perfect spot for a peaceful getaway surrounded by nature. We made some great memories here and would definitely love to come back!"
United States
Stacie L.
The price is HK$1,309
HK$2,676 total
includes taxes & fees
11 Jan - 12 Jan 2026
Tranquil Redwood Retreat
Property grounds
Backyard Garden Oasis

Cottage in Middletown

Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is HK$1,381
HK$1,539 total
includes taxes & fees
29 Dec - 30 Dec
Backyard Garden Oasis
Meeting facility
Mandala Springs Wellness Retreat Center

Aparthotel in Cobb

Mandala Springs Wellness Retreat Center
3.5 star property
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
United States
Belwadi
The price is HK$1,252
HK$1,396 total
includes taxes & fees
29 Dec - 30 Dec
Mandala Springs Wellness Retreat Center
Property grounds
Sebastopol Lux Walk toTown Guest Suite

Aparthotel in Sebastopol

Sebastopol Lux Walk toTown Guest Suite
9.0 out of 10, Wonderful, (2)
"This is a wonderful place to stay in Sebastopol. It is comfortable, cosy, quiet and well appointed - comparable to a suite in a nice hotel. There is good access, parking and a great location. Everything worked perfectly. The only issue is that entry to the room is via a spiral stair case that would be difficult for some people with disabilities. "
United States
Joe B.
The price is HK$1,061
HK$1,934 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sebastopol Lux Walk toTown Guest Suite
Outdoor dining
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Cabin in Guerneville

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
10.0 out of 10, Exceptional, (1)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
The price is HK$1,189
HK$3,722 total
includes taxes & fees
4 Jan - 5 Jan 2026
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Exterior detail
Cobb Mountain Chalet Main For

Holiday Home in Cobb

Cobb Mountain Chalet Main For
9.6 out of 10, Exceptional, (14)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is HK$606
HK$1,438 total
includes taxes & fees
19 Jan - 20 Jan 2026
Cobb Mountain Chalet Main For
Outdoor dining
The Tiny Tipsy Turtle

Cabin in Guerneville

The Tiny Tipsy Turtle
2.0 star property
10.0 out of 10, Exceptional, (42)
"Great location to walk to town!"
United States
Brenda R.
The price is HK$762
HK$1,498 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Tiny Tipsy Turtle
Interior
Russian River Retreat! Woodsy Guerneville Bungalow

Cottage in Guerneville

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
The price is HK$1,329
HK$3,354 total
includes taxes & fees
29 Dec - 30 Dec
Russian River Retreat! Woodsy Guerneville Bungalow
Fridge, microwave, oven, stovetop
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Cottage in Dillon Beach

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
10.0 out of 10, Exceptional, (59)
"This cottage was so cute! So close to the beach, super comfortable beds, and Valerie was an awesome host! This is a must stay if you are looking for a place in Dillon beach "
United States
Lauren S.
The price is HK$2,091
HK$4,393 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Beach
Wine Country Cottage in downtown Santa Rosa, CA

Cottage in Santa Rosa

Wine Country Cottage in downtown Santa Rosa, CA
9.8 out of 10, Exceptional, (62)
"Tim and Caroline’s cottage was perfect for our two night stay. We loved how close it was to the shops and restaurants in downtown Santa Rosa. Definitely recommend."
United States
Adam R.
The price is HK$1,329
HK$2,973 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wine Country Cottage in downtown Santa Rosa, CA
Terrace/patio
Escape to Wine County in your independant Cottage in Downtown Calistoga

Cottage in Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
9.6 out of 10, Exceptional, (30)
"Great getaway for a couple"
United States
David G.
The price is HK$2,137
HK$2,935 total
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Wine County in your independant Cottage in Downtown Calistoga
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

Holiday Home in Northwest Santa Rosa

Wineries & Wine: A Comforting Getaway in Wine Country
9.4 out of 10, Exceptional, (22)
"This is a great location, and comfortable space for us to tour wine country! We enjoyed the condo, it was quite and clean."
United States
Gayle C.
The price is HK$1,041
HK$2,831 total
includes taxes & fees
21 Jan - 22 Jan 2026
Wineries & Wine: A Comforting Getaway in Wine Country
Terrace/patio
Escape to Wine Country in your independant Cottage in Downtown Calistoga

Cottage in Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
10.0 out of 10, Exceptional, (2)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
The price is HK$2,137
HK$2,904 total
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Terrace/patio
Russian River Retreat! Woodsy Guerneville Bungalow

Holiday Home in Guerneville

Russian River Retreat! Woodsy Guerneville Bungalow
2.0 star property
The price is HK$1,189
HK$3,383 total
includes taxes & fees
29 Dec - 30 Dec
Russian River Retreat! Woodsy Guerneville Bungalow
Terrace/patio
Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included

Holiday Home in Kenwood

Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included
4.5 star property
9.0 out of 10, Wonderful, (2)
"Such a cute place! The turn into the property is a bit hidden right before the bridge but once you find it the house is so secluded with plenty of space. The kitchen was fully stocked and had everything you could think of. Did a wine tasting with their tasting room and everyone was so welcoming and sweet. Thank you! "
United States
Sara W.
The price is HK$3,101
HK$3,784 total
includes taxes & fees
29 Dec - 30 Dec
Vineyard Cottage • Hot Tub • Bottle of Wine & Wine Tasting Included
TV, fireplace
Russian River Brew-cation Home

Holiday Home in Northwest Santa Rosa

Russian River Brew-cation Home
10.0 out of 10, Exceptional, (55)
"This house was perfect for our wine/beer getaway. The house was spacious, the kitchen had everything you need, and the beds were very comfortable. We also loved the view from the back porch spending each morning there with a cup of coffee. The location to everything was fantastic. It was a short drive to many wineries, breweries, and restaurants. We would definitely stay here again!!"
United States
Carol H.
The price is HK$1,189
HK$3,352 total
includes taxes & fees
5 Jan - 6 Jan 2026
Russian River Brew-cation Home
Interior
Walk to Russian River - Casa Del Rio - Unit A

Holiday Home in Forestville

Walk to Russian River - Casa Del Rio - Unit A
9.2 out of 10, Wonderful, (38)
"Impressed with how close it is in walking distance to the water really appreciated the gated parking area. "
United States
Sheree L.
The price is HK$855
HK$2,994 total
includes taxes & fees
4 Jan - 5 Jan 2026
Walk to Russian River - Casa Del Rio - Unit A
Interior
The Sonoma Spyglass | Incredible Views + Sauna

Cabin in Sebastopol

The Sonoma Spyglass | Incredible Views + Sauna
2.0 star property
10.0 out of 10, Exceptional, (5)
"This stay exceeded our expectations. Absolutely stunning and such a nice place for a staycation! 5 Stars across the board for everything. Will definitely book this place again in the future."
United States
Michael
The price is HK$3,878
HK$6,389 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Sonoma Spyglass | Incredible Views + Sauna
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

Golden Haven Hot Springs

Golden Haven Hot Springs

10/10 Excellent
"Always a great experience! Girls' trip for my Birthday and was so much fun!"
Susan Taras 1-night trip
Posted 21 hours ago
Golden Haven Hot Springs

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 Dom Whitney Tasting Lounge, 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 wineries and top-notch restaurants. 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?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: This holiday home rental outside of Windsor is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals are there in Windsor?

Choose from 29 Expedia holiday rentals in Windsor for a memorable holiday.

What can I see and do in Windsor?

Family-friendly attractions include Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor, whereas Russian River is a spot to enjoy the outdoors. 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.