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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Windsor vacation rentals

A heated pool
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

Condo in Windsor

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
9.2 out of 10, Wonderful, (43)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
$337 nightly
The price is $373
Jan 8 - Jan 9
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining
Elegant Vineyard Living at a Private Wine Country Estate

Vacation Home in Windsor

Elegant Vineyard Living at a Private Wine Country Estate
8.0 out of 10, Very Good, (5)
$1,141 nightly
The price is $1,281
Jan 22 - Jan 23
Total with taxes and fees
Elegant Vineyard Living at a Private Wine Country Estate
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
$59 nightly
The price is $68
Jan 8 - Jan 9
Total with taxes and fees
The Ranch at Lake Sonoma
Exterior
Enchanting Retreat in the heart of Redwoods

Mobile Home in Guerneville

Enchanting Retreat in the heart of Redwoods
8.8 out of 10, Excellent, (12)
"Beautiful, clean house nestled in the woods. Loved the hot tub and the fire pit in the AM. Super comfortable mattresses."
United States
Jennifer H.
$291 nightly
The price is $322
Jan 8 - Jan 9
Total with taxes and fees
Enchanting Retreat in the heart of Redwoods
TV, fireplace
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.
$311 nightly
The price is $344
Jan 8 - Jan 9
Total with taxes and fees
Tranquil Redwood Retreat
Interior
Cobb Mountain Chalet Main For

Vacation 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.
$152 nightly
The price is $167
Jan 9 - Jan 10
Total with taxes and fees
Cobb Mountain Chalet Main For
Porch
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
$178 nightly
The price is $198
Jan 9 - Jan 10
Total with taxes and fees
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
$179 nightly
The price is $200
Jan 8 - Jan 9
Total with taxes and fees
Mandala Springs Wellness Retreat Center
Room, 1 Bedroom | Living area | Smart TV
Rouge Cobb Mountain Hotel - Cabin 1

Aparthotel in Cobb

Rouge Cobb Mountain Hotel - Cabin 1
2.0 star property
$225 nightly
The price is $251
Jan 8 - Jan 9
Total with taxes and fees
Rouge Cobb Mountain Hotel - Cabin 1
Outdoor pool
2 Hidden Wine Country Gem Upstairs Unit

Vacation Home in Scenic Brush Creek

2 Hidden Wine Country Gem Upstairs Unit
9.8 out of 10, Exceptional, (22)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$238 nightly
The price is $268
Jan 11 - Jan 12
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
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.
$426 nightly
The price is $479
Jan 11 - Jan 12
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Exterior
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.
$239 nightly
The price is $255
Jan 12 - Jan 13
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite
Beach
The Tiny Tipsy Turtle

Cabin in Guerneville

The Tiny Tipsy Turtle
2.0 star property
10.0 out of 10, Exceptional, (44)
"Great location to walk to town!"
United States
Brenda R.
$181 nightly
The price is $193
Jan 14 - Jan 15
Total with taxes and fees
The Tiny Tipsy Turtle
Interior
Russian River Retreat! Woodsy Guerneville Bungalow

Cottage in Guerneville

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
$382 nightly
The price is $432
Jan 8 - Jan 9
Total with taxes and fees
Russian River Retreat! Woodsy Guerneville Bungalow
Interior
2BR Bungalow | Russian River & Wine Country

Vacation Home in Forestville

2BR Bungalow | Russian River & Wine Country
10.0 out of 10, Exceptional, (4)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
$361 nightly
The price is $405
Jan 8 - Jan 9
Total with taxes and fees
2BR Bungalow | Russian River & Wine Country
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

Vacation 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.
$317 nightly
The price is $356
Jan 8 - Jan 9
Total with taxes and fees
Wineries & Wine: A Comforting Getaway in Wine Country
Terrace/patio
Escape to wine country in your independent cottage in downtown Calistoga

Cottage in Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
10.0 out of 10, Exceptional, (3)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveler
$278 nightly
The price is $335
Jan 8 - Jan 9
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
Dining
Comfort and Style in Our Queen Cottage

Cottage in Calistoga

Comfort and Style in Our Queen Cottage
9.8 out of 10, Exceptional, (49)
"The cottage was very well appointed, very clean and comfortable. we really enjoyed our 2 night stay!Communication, check in and out were a breeze!Thank you!!"
United States
Kevin T.
$359 nightly
The price is $430
Jan 8 - Jan 9
Total with taxes and fees
Comfort and Style in Our Queen Cottage
Exterior
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.
$308 nightly
The price is $369
Jan 8 - Jan 9
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
Terrace/patio
Glen Ellen Retreat #2 King Beds

Vacation Home in Glen Ellen

Glen Ellen Retreat #2 King Beds
10.0 out of 10, Exceptional, (159)
"Excellent place to stay with 4 people. The place was quiet, clean and spacious and we loved the back yard! We would definitely stay here again when visiting Sonoma,"
United States
Pam S.
$367 nightly
The price is $408
Jan 8 - Jan 9
Total with taxes and fees
Glen Ellen Retreat #2 King Beds
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
"The staff is very friendly. We arrived early in a rainy day. Luckily the staff allowed us to check in early. The hot spa is excellent. One minus is the TV connection is not very stable. It probably may be affected by the stormy weather! "
Monica 1-night trip
Posted 1 day ago
Golden Haven Hot Springs

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $68 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Dom Whitney Tasting Lounge, 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 wineries and top-notch restaurants. 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?

ON A BLUFF WITH 180 DEGREE CLOSE WATER VIEWS SHORT WALK TO THE BEACH: Visitors like this Windsor vacation home rental. It is located by the ocean and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

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?

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 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.