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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Windsor

Exterior
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)
"Great location near brewing restaurant, great amenities for kids. Place was bigger than expected and fit adults and kids comfortably. Easy parking and access.Only complaint was that the timeshare staff spent 15 mins with me after checkin trying to get me to signup for a time share meeting, when I was alone trying to watch my two young children who did not want to sit still. I didn’t realize it was a timeshare facility and that might be my fault. "
United States
Nicole D.
The price is ￥34,520
￥86,051 total
includes taxes & fees
Nov 24 - Nov 25
Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6
Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Private Vineyard Estate | Sleeps 10

Windsor
10.0 out of 10, Exceptional, (2)
"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.
The price is ￥79,472
￥168,173 total
includes taxes & fees
Nov 10 - Nov 11
Private Vineyard Estate | Sleeps 10
Front of property
The Ranch at Lake Sonoma

The Ranch at Lake Sonoma

1.0 star property
Geyserville
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
United States
Tamara
The price is ￥12,151
￥13,852 total
includes taxes & fees
Nov 10 - Nov 11
The Ranch at Lake Sonoma
Exterior
Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods

Guerneville
8.8 out of 10, Excellent, (12)
"The property/rental itself is vety nice and well appointed. However, the location leaves a little to be desired. It's essentially a trailer park and not the "nestled in the redwoods" place we were thinking it would be. Property owner/manager was very responsive throughout the rental process."
United States
Tim L.
The price is ￥25,848
￥52,209 total
includes taxes & fees
Nov 10 - Nov 11
Enchanting Retreat in the heart of Redwoods
Meeting facility
Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center

3.5 star property
Kelseyville
8.6 out of 10, Excellent, (27)
"Everything was great ... except the people staying next door in the cabin to me intruded in my space. This had nothing to do with the property though just rude bad manner people. The property folks were amazing about communicating. The site is very nice and the new cabins are terrific."
United States
Lisa
The price is ￥24,716
￥38,678 total
includes taxes & fees
Nov 10 - Nov 11
Mandala Springs Wellness Retreat Center
Property grounds
Backyard Garden Oasis

Backyard Garden Oasis

3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Greta was an amazing host, which made for a restful couple of days. Enjoyed the homemade goodies each morning"
United States
les
The price is ￥29,763
￥33,186 total
includes taxes & fees
Nov 10 - Nov 11
Backyard Garden Oasis
Property grounds
Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite

Sebastopol
10.0 out of 10, Exceptional, (1)
"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 ￥20,942
￥39,411 total
includes taxes & fees
Nov 12 - Nov 13
Sebastopol Lux Walk toTown Guest Suite
Exterior detail
Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For

Cobb
9.6 out of 10, Exceptional, (14)
"Just what we needed while visiting our family."
United States
Jason O.
The price is ￥13,117
￥29,669 total
includes taxes & fees
Nov 10 - Nov 11
Cobb Mountain Chalet Main For
Outdoor dining
The Tiny Tipsy Turtle

The Tiny Tipsy Turtle

2.0 star property
Guerneville
10.0 out of 10, Exceptional, (40)
"Property was an advertised. Host was easy to communicate with. Easy to walk to restaurants in downtown Guerneville "
United States
Elizabeth
The price is ￥15,035
￥29,880 total
includes taxes & fees
Nov 12 - Nov 13
The Tiny Tipsy Turtle
Interior
Walk to Russian River - Casa Del Rio - Unit A

Walk to Russian River - Casa Del Rio - Unit A

Forestville
9.2 out of 10, Wonderful, (38)
"Lovely home for a holiday get away"
United States
Cleo C.
The price is ￥16,876
￥59,097 total
includes taxes & fees
Nov 17 - Nov 18
Walk to Russian River - Casa Del Rio - Unit A
Outdoor dining
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)
"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 ￥31,911
￥84,169 total
includes taxes & fees
Nov 11 - Nov 12
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
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, (76)
"Very clean and excellent location."
United States
carrie k.
The price is ￥23,013
￥59,558 total
includes taxes & fees
Nov 16 - Nov 17
Glen Ellen Retreat #1 Hot Tub and King Beds
Room, 1 Bedroom | Living area | Smart TV
Rouge Cobb Mountain Hotel - Cabin 1

Rouge Cobb Mountain Hotel - Cabin 1

3.0 star property
Cobb
The price is ￥17,517
￥33,345 total
includes taxes & fees
Nov 12 - Nov 13
Rouge Cobb Mountain Hotel - Cabin 1
Dining
Colorful home & beautiful garden, ten minute walk to downtown

Colorful home & beautiful garden, ten minute walk to downtown

Burbank Gardens Neighborhood Association
9.8 out of 10, Exceptional, (17)
"My little family stayed at Nile's home and had a nice stay. The kids loved the big screen to watch cartoons and enjoyed the beautiful yard and lemon tree! Clean and cozy home. "
United States
Sonja W.
The price is ￥19,945
￥49,095 total
includes taxes & fees
Nov 10 - Nov 11
Colorful home & beautiful garden, ten minute walk to downtown
Outdoor dining
Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds

Glen Ellen
10.0 out of 10, Exceptional, (66)
"This was a wonderful place to stay and I highly recommend!"
United States
Jonathan M.
The price is ￥23,013
￥59,711 total
includes taxes & fees
Nov 12 - Nov 13
Glen Ellen Retreat #3 King Beds
Dining
Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage

Calistoga
9.8 out of 10, Exceptional, (49)
"Nice location and space was very comfortable"
United States
Tracy T.
The price is ￥25,161
￥67,132 total
includes taxes & fees
Nov 17 - Nov 18
Comfort and Style in Our Queen Cottage
Beach
Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA

Santa Rosa
9.8 out of 10, Exceptional, (60)
"Wonderful and charming cottage! Great location ... shops and restaurants close by within casual walking distance. Super clean with every amenity we needed. Hosts were communicative and very responsive to questions upon our arrival. Thank you, Tim and Caroline!"
United States
Raymond L.
The price is ￥29,150
￥63,179 total
includes taxes & fees
Nov 10 - Nov 11
Wine Country Cottage in downtown Santa Rosa, CA
Interior
Norcal Hideaway

Norcal Hideaway

Guerneville
10.0 out of 10, Exceptional, (11)
"This house is close to town and the redwoods are indeed growing right through the deck and all around the house and neighborhood; you are in the woods. The house is a bit quirky but everything you need is included and we would recommend. "
United States
Rob A.
The price is ￥36,292
￥83,433 total
includes taxes & fees
Nov 17 - Nov 18
Norcal Hideaway
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, (16)
"Our stay at Kellie's Dillon Beach home was so very comfortable and had everything we needed. Super comfortable bed, awesome kitchen and loved the patios!"
United States
Nancy F.
The price is ￥24,701
￥70,482 total
includes taxes & fees
Nov 10 - Nov 11
Bright and modern - Water views - Close to beach
Outdoor dining
Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!

Sebastopol
9.8 out of 10, Exceptional, (8)
"Kitchen overhead light broken, kitchen sink sprayer broken, window lock broken, complicated unfamiliar coffee maker with no instructions. "
United States
Kristen
The price is ￥22,246
￥53,083 total
includes taxes & fees
Dec 9 - Dec 10
Peaceful, charming, cottage in wine country. Beautiful yard!
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

The Inn at the Tides

The Inn at the Tides

10/10 Excellent
"We had nice room with a beautiful view. Our room was on the ground floor which allowed us to have a patio that out looked the surrounding gardens and a peek of the ocean."
Padragin A 1-night trip
Posted 1 day ago
The Inn at the Tides

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 top-notch restaurants and wineries. 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 32 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.