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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Windham cottages

Property grounds

Tiny House on Walnut Grove

Tiny House on Walnut Grove
Ashland
4.0 out of 10, (2 reviews)
"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.
$261 nightly
The price is $281
Apr 13 - Apr 14
Total with taxes and fees
Tiny House on Walnut Grove
House (4 Bedrooms) | Interior

'the Mountain House:' Windham Retreat w/ Hot Tub!

'the Mountain House:' Windham Retreat w/ Hot Tub!
3.0 star property
Windham
'the Mountain House:' Windham Retreat w/ Hot Tub!
Exterior

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (13 reviews)
"Very comfortable home"
United States
Holly
$267 nightly
The price is $288
Apr 15 - Apr 16
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (276 reviews)
"The view in the snow was absolutely gorgeous and the size of the accommodations was perfect!"
United States
Abigail Y.
$272 nightly
The price is $305
Apr 16 - Apr 17
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Exterior

Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (23 reviews)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
$309 nightly
The price is $346
Apr 16 - Apr 17
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Outdoor dining

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Shandaken
10.0 out of 10, Exceptional, (1 review)
"10/10 experience. beautiful cabin, super cozy"
United States
Hunter W.
$173 nightly
The price is $193
Apr 13 - Apr 14
Total with taxes and fees
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Exterior

Little red house just outside of Woodstock

Little red house just outside of Woodstock
Bearsville
9.0 out of 10, Wonderful, (2 reviews)
"The house is cute, well decorated but very small "
United States
Harry
$500 nightly
The price is $559
Apr 15 - Apr 16
Total with taxes and fees
Little red house just outside of Woodstock
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
9.0 out of 10, Wonderful, (47 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
$277 nightly
The price is $310
Apr 19 - Apr 20
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

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (22 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
$518 nightly
The price is $559
Apr 13 - Apr 14
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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Clean room, nature friendly."
Maaz 1-night trip
Posted 12 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Find out more about Windham

Windham Cottages information

Number of reviews
386
Accommodation
181 Cottages
Lowest Price
$193
Highest Price
$559

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between $193 and $559 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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