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Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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

Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Windsor
9.2 out of 10, Wonderful, (43 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
$340 nightly
The price is $376
Jan 19 - Jan 20
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

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)
"Beautiful home and property. Great location, close to so many vineyards and other places we wanted to visit. Cynthia was so great to work with! Would definitely stay here again. "
United States
Denise F.
$1,000 nightly
The price is $1,123
Jan 19 - Jan 20
Total with taxes and fees
Elegant Vineyard Living at a Private Wine Country Estate

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (17 reviews)
"Very enjoyable stay at this place. Very cute and charming and had everything we needed. Close to restaurants and shopping. I'd definitely stay here again."
United States
Anonymous traveler
$289 nightly
The price is $320
Jan 28 - Jan 29
Total with taxes and fees
Creekside Under the Redwoods

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"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 19 - Jan 20
Total with taxes and fees
Tranquil Redwood Retreat

Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.8 out of 10, Excellent, (12 reviews)
"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.
$292 nightly
The price is $323
Jan 19 - Jan 20
Total with taxes and fees
Enchanting Retreat in the heart of Redwoods

Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #1 Hot Tub and King Beds
Glen Ellen
10.0 out of 10, Exceptional, (82 reviews)
"Very clean and excellent location."
United States
carrie k.
$408 nightly
The price is $451
Jan 16 - Jan 17
Total with taxes and fees
Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (72 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
$387 nightly
The price is $428
Jan 16 - Jan 17
Total with taxes and fees
Glen Ellen Retreat #3 King Beds

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
10.0 out of 10, Exceptional, (1 review)
"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.
$430 nightly
The price is $483
Jan 19 - Jan 20
Total with taxes and fees
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (18 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
$458 nightly
The price is $515
Jan 27 - Jan 28
Total with taxes and fees
Bright and modern - Water views - Close to beach

Norcal Hideaway

Norcal Hideaway
Guerneville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful setting "
United States
LouAnn O.
$452 nightly
The price is $499
Jan 21 - Jan 22
Total with taxes and fees
Norcal Hideaway

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
$382 nightly
The price is $458
Jan 19 - Jan 20
Total with taxes and fees
Charming King Cottage

Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"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 19 - Jan 20
Total with taxes and fees
Comfort and Style in Our Queen Cottage

Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.0 out of 10, Wonderful, (2 reviews)
"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.
$241 nightly
The price is $257
Jan 21 - Jan 22
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Old Town Bodega Bay
9.4 out of 10, Exceptional, (353 reviews)
"Loved this property and the views. "
United States
anne
$501 nightly
The price is $554
Jan 19 - Jan 20
Total with taxes and fees
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!

Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (44 reviews)
"Property was true to description, clean, and communication with the owner were clear and easy."
United States
Kyle M.
$334 nightly
The price is $369
Jan 19 - Jan 20
Total with taxes and fees
Private Lofted Downtown Studio

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (4 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
2BR Bungalow | Russian River & Wine Country

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
$178 nightly
The price is $198
Jan 16 - Jan 17
Total with taxes and fees
Backyard Garden Oasis

Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries

Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries
Healdsburg
10.0 out of 10, Exceptional, (8 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
$359 nightly
The price is $397
Jan 20 - Jan 21
Total with taxes and fees
Private Vineyard-View Wine Country Home Near Healdsburg and Sonoma Wineries

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$240 nightly
The price is $270
Jan 25 - Jan 26
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit

Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (37 reviews)
"Clean and comfortable place to stay, easy-check in, good amenities and location. Would definitely stay again."
United States
Scott W.
$538 nightly
The price is $562
Jan 21 - Jan 22
Total with taxes and fees
Serenity at the Russian River
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

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.

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. Pacific Coast Air Museum and Windsor Golf Club 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.