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Check prices for these dates

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

Our top choices for Windham cottages

Property grounds
Tiny House on Walnut Grove

Cottage in Ashland

Tiny House on Walnut Grove
2.0 star property
4.0 out of 10, (2)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
$267 nightly
The price is $288
Dec 14 - Dec 15
Total with taxes and fees
Tiny House on Walnut Grove
Exterior
Country Cottage with beautiful views and easy access to Catskills activities.

Cottage in Saugerties

Country Cottage with beautiful views and easy access to Catskills activities.
10.0 out of 10, Exceptional, (13)
"Cozy and beautiful house. "
United States
Seung L.
$171 nightly
The price is $192
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Cottage with beautiful views and easy access to Catskills activities.
Exterior
Experience Peace in this Cozy country cottage nestled beneath the mountains

Cottage in Catskill

Experience Peace in this Cozy country cottage nestled beneath the mountains
9.8 out of 10, Exceptional, (9)
"Very comfortable cottage in a lovely area. Grateful for the ac on those very hot days! Loved grilling on the porch and the big patio umbrellas. Host is very responsive and helpful when needed. Hope to come again! "
United States
Laura G.
$309 nightly
The price is $334
Dec 12 - Dec 13
Total with taxes and fees
Experience Peace in this Cozy country cottage nestled beneath the mountains
Exterior
Charming Cottage in the Heart of Catskill & Pet Friendly

Cottage in Catskill

Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (18)
"We had a wonderful time at the Catskill Nook. Everything was great and the hosts were amazing. Well located, walking distance to everything and pet friendly. The flowers from our hosts were gorgeous. We had a blast. "
United States
Bernadette P.
$316 nightly
The price is $341
Dec 12 - Dec 13
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

Cottage in Phoenicia

Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
9.8 out of 10, Exceptional, (23)
"Had a wonderful "
United States
Alexandra R.
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Outdoor dining
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Cottage in Shandaken

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
$193 nightly
The price is $216
Dec 15 - Dec 16
Total with taxes and fees
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Cottage in Woodstock

Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
$301 nightly
The price is $337
Dec 13 - Dec 14
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Exterior
Little red house just outside of Woodstock

Cottage in Bearsville

Little red house just outside of Woodstock
9.0 out of 10, Wonderful, (2)
"The house is cute, well decorated but very small "
United States
Harry
$496 nightly
The price is $555
Dec 14 - Dec 15
Total with taxes and fees
Little red house just outside of Woodstock
Terrace/patio
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Cottage in woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.0 out of 10, Wonderful, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
$277 nightly
The price is $310
Dec 14 - Dec 15
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Outdoor dining
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Cottage in Maplecrest

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at the cottage. Place was perfect and met all our needs. The cottage was lovely and cozy, truly home away from home. The host, Agnes, was kind and very helpful. Will definitely be back."
United States
Carmela L.
$508 nightly
The price is $549
Dec 14 - Dec 15
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
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 Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Love this place when its available. Low key, clean and conveniently near BOTH Hunter and Windham ski areas!"
Bruce 1-night trip
Posted 2 days ago
Hotel Vienna

Find out more about Windham

Windham Cottages information

Number of reviews
352
Accommodation
180 Cottages
Lowest Price
$192
Highest Price
$555

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $192 and $555 per night. These stays offer a chance to touch base with nature — at a price you can afford. 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.
Why book your cottage in Windham with Expedia?
Expedia has some wonderful cottages in Windham, so get set for a memorable stay on nature's doorstep. If you have a budget, select how much you want to spend and the preferred star rating of your property. Or, try out our filters to search for cottages with a pool or a hot tub. We'll help you find the right place whatever your style of travel or plans.
How can I find cheap cottages in Windham?
With Expedia's convenient filter tool, sourcing cheap cottages in Windham is a snap. To discover stays that are friendly on the wallet, tailor your search results by budget, star rating and amenities.
What is there to do in Windham near my cottage?
If you're eager to fill up your itinerary in Windham, be sure to visit Windham Mountain Resort. It's popular among travelers and locals alike.

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