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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Windham cottages

A hot tub on a deck with a view of a forested hillside.

1. '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!
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, (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 CA $497
CA $776 total
includes taxes & fees
Aug 30 - Aug 31
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
A covered porch with a wooden bench, a wicker chair, and a sofa with cushions.

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 CA $179
CA $432 total
includes taxes & fees
Sep 14 - Sep 15
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

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 CA $249
CA $495 total
includes taxes & fees
Aug 31 - Sep 1
Charming Cottage in the Heart of Catskill & Pet Friendly
A wooden cabin surrounded by lush greenery and trees.

5. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (295 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 traveller
The price is CA $198
CA $436 total
includes taxes & fees
Sep 7 - Sep 8
Streamside Cottage Half Mile to Town of Woodstock
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, (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 CA $333
CA $707 total
includes taxes & fees
Aug 29 - Aug 30
Cozy 2-bedroom cottage in enchanting Catskill Mountains
An open deck with potted plants, a table, and a chair.

7. 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 CA $249
CA $430 total
includes taxes & fees
Sep 8 - Sep 9
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

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"good facility"
Andrea 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Saugerties

Find out more about Windham

Windham Cottages information

Number of reviews
116
Accommodation
189 Cottages
Lowest Price
CA $430
Highest Price
CA $776

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $430 and CA $776 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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