Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6
Windsor
10.0 out of 10, Exceptional, (1 review)
$340 nightly
The price is $376
May 17 - May 18
Total with taxes and fees
Top Wine Country Condo - Full Resort Amenity Access - 2 Bedroom/2 Bath - Sleep 6

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, (45 reviews)
"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
May 18 - May 19
Total with taxes and fees
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6
Windsor
$337 nightly
The price is $373
May 18 - May 19
Total with taxes and fees
TOP HOST - Vacation Memories Just Waiting to be Made - 2 Bedroom - Sleeps 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6
Windsor
$337 nightly
The price is $373
May 18 - May 19
Total with taxes and fees
One Click Away from Vacay - Full Resort Access - 2 Bedroom / 2 Bath - Sleep 6

Two Separate 2BR Condos w/Pool & Hot Tub

Two Separate 2BR Condos w/Pool & Hot Tub
Windsor
$4,740 nightly
The price is $4,740
May 23 - May 24
Total with taxes and fees
Two Separate 2BR Condos w/Pool & Hot Tub

Creekside Under the Redwoods

Creekside Under the Redwoods
Guerneville
9.8 out of 10, Exceptional, (20 reviews)
"Very cute and comfortable place! We enjoyed our stay!"
United States
Kathy M.
$312 nightly
The price is $345
May 17 - May 18
Total with taxes and fees
Creekside Under the Redwoods

Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (10 reviews)
"Comfortable place to stay, close to everything. Host was amazing. "
United States
Joelle S.
$312 nightly
The price is $345
May 17 - May 18
Total with taxes and fees
Tranquil Redwood Retreat

Hillside Hideaway in the Redwoods

Hillside Hideaway in the Redwoods
Guerneville
9.8 out of 10, Exceptional, (8 reviews)
"Great spot, it felt very spacious and the outdoor area is really nice too. "
United States
Kristin G.
$310 nightly
The price is $342
May 18 - May 19
Total with taxes and fees
Hillside Hideaway in the Redwoods

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (11 reviews)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
$346 nightly
The price is $389
May 19 - May 20
Total with taxes and fees
2BR Bungalow | Russian River & Wine Country

Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (46 reviews)
"Fabulous, beautiful and within walking distance to downtown!"
United States
Jacqui S.
$291 nightly
The price is $322
May 17 - May 18
Total with taxes and fees
Private Lofted Downtown Studio

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (27 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
$162 nightly
The price is $178
May 20 - May 21
Total with taxes and fees
Cobb Mountain Chalet King Size Suite

Rouge Cobb Mountain Hotel - Cabin 3

Rouge Cobb Mountain Hotel - Cabin 3
2.0 star property
Cobb
10.0 out of 10, Exceptional, (1 review)
"I love this place. The River was going on. I wish I can go every weekend there.thank you for everything. We appreciate the owner."
United States
JOSELITA
$202 nightly
The price is $226
May 19 - May 20
Total with taxes and fees
Rouge Cobb Mountain Hotel - Cabin 3

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.
$217 nightly
The price is $244
May 17 - May 18
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit

Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills

Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills
Monte Rio
9.4 out of 10, Exceptional, (19 reviews)
"Wonderfully appointed cabin in an incredibly charming location. "
United States
Shannon B.
$346 nightly
The price is $382
May 19 - May 20
Total with taxes and fees
Cozy Riverview Cottage Retreat - walk to hiking trails & downtown Duncans Mills

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (17 reviews)
"Great location on the river. Can't wait to come back in the summer."
United States
Gregg B.
$445 nightly
The price is $500
May 18 - May 19
Total with taxes and fees
Cozy Riverfront Cabin - Beach Access & Wood Stove

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)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
$361 nightly
The price is $406
May 17 - May 18
Total with taxes and fees
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (21 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
$447 nightly
The price is $502
May 20 - May 21
Total with taxes and fees
Bright and modern - Water views - Close to beach

Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (33 reviews)
"Cute house with a very well appointed kitchen, lots of games and puzzles for kids, and fun murals in the smallest bedroom. "
United States
Flynne N.
$415 nightly
The price is $461
May 17 - May 18
Total with taxes and fees
Somms Rest ⎮ Designed. Curated. Peaceful.

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
$209 nightly
The price is $233
May 22 - May 23
Total with taxes and fees
Backyard Garden Oasis

The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (55 reviews)
"Really great place. Highly recommend!!!"
United States
Jennifer
$207 nightly
The price is $221
May 25 - May 26
Total with taxes and fees
The Tiny Tipsy Turtle
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 $88 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?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—BOOK 3 NIGHTS—4th FREE! Close to EVERYTHING: 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 29 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 Pacific Coast Air Museum 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.