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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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 £311
includes taxes & fees
12 Nov - 13 Nov
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 £394
includes taxes & fees
17 Nov - 18 Nov
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A wooden deck with a table and chairs, overlooking a snowy landscape with bare trees.

3. 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, (2 reviews)
"It was a charming and cozy cabin nested in the woods. Perfect size for two people."
United States
afsoon p.
The price is £139
includes taxes & fees
7 Dec - 8 Dec
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
A wooden cabin surrounded by lush greenery and trees.

4. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (309 reviews)
"perfect for a quiet getaway for 2."
United States
Anonymous traveller
The price is £227
includes taxes & fees
12 Nov - 13 Nov
Streamside Cottage Half Mile to Town of Woodstock
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)
"Artsy, comfortable and cozy cottage in a country setting. Love the deck for grilling! This was our second time here and we hope to be back again!"
United States
Laura G.
The price is £234
includes taxes & fees
16 Nov - 17 Nov
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A single-story house with a dark exterior, a chimney, and a small window.

6. 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 £364
includes taxes & fees
12 Nov - 13 Nov
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.

7. 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, (31 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 £266
includes taxes & fees
12 Nov - 13 Nov
Charming Cottage in the Heart of Catskill & Pet Friendly
A covered outdoor area with wooden benches and a view of a green landscape.

8. Mtn-view Luxe Catskills Retreat for Groups

Mtn-view Luxe Catskills Retreat for Groups
3.0 star property
Hobart
The price is £525
includes taxes & fees
18 Nov - 19 Nov
Mtn-view Luxe Catskills Retreat for Groups
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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Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

See all hotels in Windham
Two skiers on a snowy slope with a valley and mountains in the background.

Top reviews in Windham

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.
Hotel Mountain Brook

Hotel Mountain Brook

Hotel Mountain Brook
Tannersville

10/10 Excellent

Great staff, breakfast, beautiful and clean
United Kingdom
Eban
Reviewed July 29, 2026
Hotel Mountain Brook

Frequently Asked Questions

How much do cottages in Windham cost?

Cottages in Windham range between £139 and £525 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 travellers and locals alike.