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
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Windham cottages

Outdoor dining

1. 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, (23 reviews)
"Good location at Catskills area. Family friendly, large back yard that has access to the nearby creek."
United States
Yichen
The price is AED 1,319
AED 2,051 total
includes taxes & fees
6 Sep - 7 Sep
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Property grounds

2. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (296 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveler
The price is AED 526
AED 1,119 total
includes taxes & fees
7 Sep - 8 Sep
Streamside Cottage Half Mile to Town of Woodstock
Terrace/patio

3. 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, (19 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 AED 426
AED 1,079 total
includes taxes & fees
14 Sep - 15 Sep
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

4. 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, (25 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 AED 661
AED 1,300 total
includes taxes & fees
7 Sep - 8 Sep
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior

5. Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
10.0 out of 10, Exceptional, (1 review)
"The property is great. Easy check-in and communication with host. Large property and comfortable beds."
United States
Robert G.
The price is AED 883
AED 1,877 total
includes taxes & fees
7 Sep - 8 Sep
Cozy 2-bedroom cottage in enchanting Catskill Mountains
Terrace/patio

6. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
8.8 out of 10, Excellent, (48 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is AED 671
AED 1,155 total
includes taxes & fees
8 Sep - 9 Sep
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"Great location to amazing trails and great accommodations"
Nuria 2-night trip
Posted 6 hours ago
Kaatskill Mountain Club & Condos by Vail Resorts

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between AED 1,079 and AED 2,051 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.