Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Windsor vacation rentals

A heated pool

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, (44 reviews)
"Check-in was a little difficult, but the condo itself was convenient and a great stay."
United States
SB L.
The price is ￥31,444
￥58,624 total
includes taxes & fees
Feb 10 - Feb 11
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Dining

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)
"Stayed here for a wedding "
United States
Lanna E.
The price is ￥58,643
￥144,048 total
includes taxes & fees
Feb 10 - Feb 11
Elegant Vineyard Living at a Private Wine Country Estate
TV, fireplace

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.
The price is ￥23,772
￥50,301 total
includes taxes & fees
Feb 10 - Feb 11
Tranquil Redwood Retreat
Terrace/patio

Glen Ellen Retreat #2 King Beds

Glen Ellen Retreat #2 King Beds
Glen Ellen
10.0 out of 10, Exceptional, (159 reviews)
"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.
The price is ￥25,941
￥64,303 total
includes taxes & fees
Feb 10 - Feb 11
Glen Ellen Retreat #2 King Beds
Terrace/patio

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.
The price is ￥27,514
￥66,222 total
includes taxes & fees
Feb 10 - Feb 11
Glen Ellen Retreat #1 Hot Tub and King Beds
Outdoor pool

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.
The price is ￥18,253
￥42,080 total
includes taxes & fees
Feb 10 - Feb 11
2 Hidden Wine Country Gem Upstairs Unit
Exterior

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is ￥29,715
￥74,092 total
includes taxes & fees
Feb 10 - Feb 11
Charming King Cottage
Property grounds

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, (355 reviews)
"Loved this property and the views. "
United States
anne
The price is ￥39,934
￥86,106 total
includes taxes & fees
Feb 10 - Feb 11
Romantic King Bed Studio ~ STUNNING VIEWS Bodega Bay - Perched over the water!
Living area

Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (28 reviews)
"Very clean room, friendly staff, great to walk around "
United States
Victoria
The price is ￥25,328
￥28,240 total
includes taxes & fees
Mar 8 - Mar 9
Mandala Springs Wellness Retreat Center
Porch

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
The price is ￥27,930
￥31,142 total
includes taxes & fees
Feb 10 - Feb 11
Backyard Garden Oasis
Outdoor dining

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.
The price is ￥25,784
￥72,450 total
includes taxes & fees
Feb 10 - Feb 11
Bright and modern - Water views - Close to beach
Interior

The Sonoma Spyglass | Incredible Views + Sauna

The Sonoma Spyglass | Incredible Views + Sauna
Sebastopol
10.0 out of 10, Exceptional, (5 reviews)
"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 ￥52,354
￥96,715 total
includes taxes & fees
Feb 10 - Feb 11
The Sonoma Spyglass | Incredible Views + Sauna
Smart TV, fireplace

“NEW” Half Moon Retreat / +Pool Table / - 5 min away from GRATON casino

“NEW” Half Moon Retreat / +Pool Table / - 5 min away from GRATON casino
Southwest Santa Rosa
10.0 out of 10, Exceptional, (6 reviews)
"Myself and four guests thoroughly enjoyed our overnight stay! The home had everything we needed and more - clean, cozy, and beautifully equipped with wonderful amenities. The beds were incredibly comfortable, and our host was very welcoming and attentive. We couldn’t have asked for a better experience. Highly recommend!"
United States
JoAnn P.
The price is ￥50,185
￥56,631 total
includes taxes & fees
Feb 10 - Feb 11
“NEW” Half Moon Retreat / +Pool Table / - 5 min away from GRATON casino
Dining

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.
The price is ￥26,570
￥69,917 total
includes taxes & fees
Feb 10 - Feb 11
Comfort and Style in Our Queen Cottage
Dining

Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (30 reviews)
"This Smart home is very comfortable and well equipped. Beds are super comfy! Perfect for our girls weekend!"
United States
Mary K.
The price is ￥48,848
￥110,051 total
includes taxes & fees
Feb 10 - Feb 11
Wine Country Getaway
Fridge, microwave, oven, stovetop

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog

Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Dillon Beach
10.0 out of 10, Exceptional, (64 reviews)
"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 ￥42,308
￥88,557 total
includes taxes & fees
Feb 11 - Feb 12
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
TV

Emerald Lodge quiet efficiency

Emerald Lodge quiet efficiency
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is ￥14,464
￥33,296 total
includes taxes & fees
Feb 10 - Feb 11
Emerald Lodge quiet efficiency
Beach towels

Harbor Kee Peaceful Escape By The Bay

Harbor Kee Peaceful Escape By The Bay
Bodega Bay
9.6 out of 10, Exceptional, (24 reviews)
"We really enjoyed the historic home. Centrally located, close the restaurants "
United States
Pati K.
The price is ￥28,300
￥81,157 total
includes taxes & fees
Feb 16 - Feb 17
Harbor Kee Peaceful Escape By The Bay
Interior

Norcal Hideaway

Norcal Hideaway
Guerneville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful setting "
United States
LouAnn O.
The price is ￥24,644
￥70,346 total
includes taxes & fees
Feb 11 - Feb 12
Norcal Hideaway
2 bedrooms, desk, iron/ironing board, free WiFi

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (65 reviews)
"Good location for coffee and restaurant. Nice backyard "
United States
vicki a.
The price is ￥29,125
￥60,448 total
includes taxes & fees
Feb 10 - Feb 11
Wine Country Cottage in downtown Santa Rosa, CA
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

La Quinta Inn & Suites Santa Rosa Sonoma

La Quinta Inn & Suites Santa Rosa Sonoma

10/10 Excellent
"Very, very clean hotel and room, our room smelled great, everything was in tip top shape. We were very impressed with how clean the whole property was. Breakfast was included with enough options for everyone to be satisfied. I would absolutely stay here again."
Ivana 3-night trip
Posted 1 day ago
La Quinta Inn & Suites Santa Rosa Sonoma

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 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?

Bodega Bay on the Edge of Pacific Ocean: Visitors like this Windsor vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

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.