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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

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.
The price is CA $179
CA $347 total
includes taxes & fees
Mar 1 - Mar 2
Tiny House on Walnut Grove
Exterior

Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
10.0 out of 10, Exceptional, (15 reviews)
"Cozy and beautiful house. "
United States
Seung L.
The price is CA $152
CA $265 total
includes taxes & fees
Feb 19 - Feb 20
Country Cottage with beautiful views and easy access to Catskills activities.
Exterior

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

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
10.0 out of 10, Exceptional, (12 reviews)
"Very comfortable home"
United States
Holly
The price is CA $189
CA $444 total
includes taxes & fees
Feb 17 - Feb 18
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
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
The price is CA $398
CA $771 total
includes taxes & fees
Feb 17 - Feb 18
Little red house just outside 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, (22 reviews)
"Really comfortable and cozy"
Canada
Lynne H.
The price is CA $239
CA $461 total
includes taxes & fees
Feb 21 - Feb 22
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.
The price is CA $154
CA $284 total
includes taxes & fees
Mar 2 - Mar 3
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
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, (46 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is CA $245
CA $427 total
includes taxes & fees
Feb 22 - Feb 23
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, (21 reviews)
"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.
The price is CA $489
CA $772 total
includes taxes & fees
Feb 17 - Feb 18
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

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10/10 Excellent
"The house was perfectly clean and so very comfortable. And the host was very responsive. EXCELLENT experience all around!"
Lisa T. 2-night trip
Posted 2 days ago
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Find out more about Windham

Windham Cottages information

Number of reviews
110
Accommodation
180 Cottages
Lowest Price
CA $265
Highest Price
CA $772

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $265 and CA $772 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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