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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Windsor cottages

Exterior

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 31 - Feb 1
Total with taxes and fees
Backyard Garden Oasis
Outdoor dining

Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (1 review)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
United States
kelsie i.
$199 nightly
The price is $219
Jan 30 - Jan 31
Total with taxes and fees
Garden house with gas fireplace
Interior

Russian River Retreat! Woodsy Guerneville Bungalow

Russian River Retreat! Woodsy Guerneville Bungalow
3.0 star property
Guerneville
$382 nightly
The price is $432
Feb 1 - Feb 2
Total with taxes and fees
Russian River Retreat! Woodsy Guerneville Bungalow
Property grounds

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.
$371 nightly
The price is $445
Feb 1 - Feb 2
Total with taxes and fees
Comfort and Style in Our Queen Cottage
Terrace/patio

Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (3 reviews)
"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
$315 nightly
The price is $378
Feb 1 - Feb 2
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
Exterior

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, (63 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.
$500 nightly
The price is $562
Feb 1 - Feb 2
Total with taxes and fees
Sundog Cottage - Clean & Cozy - EV - Walk to Food & Beach - Fenced Yard for Dog
Exterior

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)
"Tim and Caroline’s cottage was perfect for our two night stay. We loved how close it was to the shops and restaurants in downtown Santa Rosa. Definitely recommend."
United States
Adam R.
$384 nightly
The price is $407
Feb 1 - Feb 2
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
Exterior

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
$393 nightly
The price is $471
Feb 1 - Feb 2
Total with taxes and fees
Charming King Cottage
Exterior

Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
Calistoga
9.6 out of 10, Exceptional, (32 reviews)
"Great getaway for a couple"
United States
David G.
$315 nightly
The price is $378
Feb 1 - Feb 2
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
Exterior

Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (2 reviews)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
$313 nightly
The price is $376
Feb 1 - Feb 2
Total with taxes and fees
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Terrace/patio

Stunning Sauna Cottage Retreat on Private Vineyard

Stunning Sauna Cottage Retreat on Private Vineyard
Sebastopol
10.0 out of 10, Exceptional, (3 reviews)
"Nice area in the vineyards. Sauna was great. Place was clean. "
United States
Cesar R.
$468 nightly
The price is $518
Feb 3 - Feb 4
Total with taxes and fees
Stunning Sauna Cottage Retreat on Private Vineyard
Exterior

The Atlas Calistoga - Cottage #3

The Atlas Calistoga - Cottage #3
Calistoga
10.0 out of 10, Exceptional, (20 reviews)
"Great cottage within walking distance to downtown Calistoga."
United States
Joel S.
$492 nightly
The price is $557
Feb 8 - Feb 9
Total with taxes and fees
The Atlas Calistoga - Cottage #3
Microwave, oven, stovetop, dishwasher

Enchanting Vineyard cottage nestled in the wine country!

Enchanting Vineyard cottage nestled in the wine country!
Santa Rosa
$635 nightly
The price is $701
Feb 2 - Feb 3
Total with taxes and fees
Enchanting Vineyard cottage nestled in the wine country!
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

Holiday Inn Windsor Wine Country by IHG

Holiday Inn Windsor Wine Country by IHG

10/10 Excellent
"Quiet. Convenient right of freeway."
Dolores 1-night trip
Posted 4 days ago
Holiday Inn Windsor Wine Country by IHG

Find out more about Windsor

Windsor Cottages information

Number of reviews
300
Accommodation
124 Cottages
Lowest Price
$198
Highest Price
$562

Frequently asked questions

How much do cottages in Windsor cost?
Rates for cottages in Windsor range between $198 and $562 per night. No matter your budget, you'll find the perfect place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Windsor?
Pack your bags and pick from 124 cottages in Windsor. Thinking about a place where you can relax and connect with nature? Expedia can help you find your ideal stay in a few simple clicks.
Are there any family-friendly cottages in Windsor?
Put your bags down at Wine Country Getaway Modern Three and make your family getaway to Windsor nice and comfortable. This family-friendly cottage has a 3-star rating and conveniences such as an oven and WiFi. Once you've checked in and dropped off your bags, there are loads of family-friendly attractions to explore in and around Windsor. Safari West and Rubicon Adventures guarantee a good time for young and old.
Why book your cottage in Windsor with Expedia?
Reserving a cottage in Windsor is as simple as deciding on your travel dates and picking an ideal place for outdoor relaxation and recreation. From ritzy retreats to affordable properties and cottages that come with amenities like laundry facilities, Expedia has something for all traveler tastes. As for the best offers around? We've got them too!
How can I find cheap cottages in Windsor?
The best way to compare cheap cottages in Windsor is with Expedia's filter tool. Refine your search by star rating, amenities and budget to nab unbeatable prices in just a few keystrokes.
What is there to do in Windsor near my cottage?
Windsor has enough activities and experiences to keep you going for weeks, beginning with Pacific Coast Air Museum. Windsor Golf Club, Sonoma-Cutrer Vineyards Cutrer Vineyard and Russian Hill Estate Vineyards are other awesome attractions. If you're hanging around a while, Windsor Oaks Vineyards and Powell's Sweet Shoppe - Windsor are nice finishing touches to your itinerary.

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