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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Cottages in Windsor

Outdoor dining
Garden house with gas fireplace

Garden house with gas fireplace

Middletown
10.0 out of 10, Exceptional, (1)
"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.
Garden house with gas fireplace
Exterior
Backyard Garden Oasis

Backyard Garden Oasis

3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is AED 768
AED 856 total
includes taxes & fees
10 Dec - 11 Dec
Backyard Garden Oasis
Property grounds
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

Forestville
10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
The price is AED 735
AED 1,817 total
includes taxes & fees
10 Dec - 11 Dec
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
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, (58)
"Clean room | pet friendly | very attentive | excellent host | very friendly | took my 10 year old son and she welcomed him with a gift in his room "
United States
Crystal
The price is AED 988
AED 2,069 total
includes taxes & fees
10 Dec - 11 Dec
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
9.8 out of 10, Exceptional, (62)
"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.
The price is AED 716
AED 1,533 total
includes taxes & fees
8 Jan - 9 January 2026
Wine Country Cottage in downtown Santa Rosa, CA
Property grounds
Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage

Calistoga
9.8 out of 10, Exceptional, (49)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
The price is AED 657
AED 1,678 total
includes taxes & fees
21 Dec - 22 Dec
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)
"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
The price is AED 1,010
AED 1,347 total
includes taxes & fees
4 Jan - 5 January 2026
Escape to wine country in your independent cottage in downtown Calistoga
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, (30)
"Great place! Clean, and very close to everything!"
United States
Levi J.
The price is AED 1,010
AED 1,328 total
includes taxes & fees
4 Jan - 5 January 2026
Escape to Wine County in your independant Cottage in Downtown Calistoga
Property grounds
Charming King Cottage

Charming King Cottage

Calistoga
9.8 out of 10, Exceptional, (11)
"This property was amazing!! Very clean, comfortable and exactly as described in the listing. Our host reached out personally to make sure we had the check in instructions. When we come back to Calistoga we will stay here again!!"
United States
Rich S.
The price is AED 694
AED 1,731 total
includes taxes & fees
4 Jan - 5 January 2026
Charming King Cottage
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)
"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
The price is AED 1,010
AED 1,347 total
includes taxes & fees
4 Jan - 5 January 2026
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Property grounds
Stunning Sauna Cottage Retreat on Private Vineyard

Stunning Sauna Cottage Retreat on Private Vineyard

Sebastopol
10.0 out of 10, Exceptional, (3)
"Nice area in the vineyards. Sauna was great. Place was clean. "
United States
Cesar R.
The price is AED 1,139
AED 1,902 total
includes taxes & fees
10 Dec - 11 Dec
Stunning Sauna Cottage Retreat on Private Vineyard
Exterior
Relaxing Beekeeper's Cottage with hot tub

Relaxing Beekeeper's Cottage with hot tub

Bodega Bay
10.0 out of 10, Exceptional, (21)
"A Lovely tucked away Cottage, with relaxing amenities, close to everything Bodega Bay has to offer"
United States
Brian K.
The price is AED 1,370
AED 2,486 total
includes taxes & fees
22 Dec - 23 Dec
Relaxing Beekeeper's Cottage with hot tub
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

Hotel E

Hotel E

10/10 Excellent
"Lovely historic property, friendly staff, quiet and comfortable room, great bed. Plus I parked in a city lot one block away that cost me 50 cents for two nights! "
David John 2-night trip
Posted 5 hours ago
Hotel E

Frequently asked questions

How much do cottages in Windsor cost?
Rates for cottages in Windsor range between AED 856 and AED 2,486 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.
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.