A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Windham cottages

A snow-covered ground with footprints leading to a house with a solar panel roof.

1. 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 $285
CA $610 total
includes taxes & fees
Oct 26 - Oct 27
Tiny House on Walnut Grove
A wooden deck with a white railing, surrounded by lush green trees.

2. 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, (25 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is CA $505
CA $797 total
includes taxes & fees
Oct 26 - Oct 27
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A hot tub on a covered porch with a view of a wooded area.

3. Private Hot tub Modern house Near Ski resorts and Catskill

Private Hot tub Modern house Near Ski resorts and Catskill
Elka Park
8.8 out of 10, Excellent, (9 reviews)
"Access to house was easy, close to tons of hiking trails, clean house, great place to unwind and explore!"
United States
Anonymous traveller
The price is CA $379
CA $826 total
includes taxes & fees
Nov 7 - Nov 8
Private Hot tub Modern house Near Ski resorts and Catskill
A wooden deck with a table and chairs, overlooking a snowy landscape with bare trees.

4. 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 $144
CA $274 total
includes taxes & fees
Nov 3 - Nov 4
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

5. 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, (21 reviews)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
The price is CA $172
CA $447 total
includes taxes & fees
Nov 3 - Nov 4
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A wooden cabin surrounded by lush greenery and trees.

6. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (305 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
The price is CA $214
CA $462 total
includes taxes & fees
Nov 10 - Nov 11
Streamside Cottage Half Mile to Town of Woodstock
A single-story house with a dark exterior, a chimney, and a small window.

7. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (2 reviews)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is CA $338
CA $720 total
includes taxes & fees
Oct 30 - Oct 31
Cozy 2-bedroom cottage in enchanting Catskill Mountains
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

8. 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, (26 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
The price is CA $253
CA $502 total
includes taxes & fees
Oct 29 - Oct 30
Charming Cottage in the Heart of Catskill & Pet Friendly
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Rooms we r e redone. Simple breakfast but sufficient. Ski lodge right near hunter ski area.front desk great"
ronald 1-night trip
Posted 10 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Windham

Windham Cottages information

Number of reviews
388
Accommodation
188 Cottages
Lowest Price
CA $447
Highest Price
CA $826

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $447 and CA $826 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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