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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Windham cottages

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, (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 $503
CA $791 total
includes taxes & fees
Jul 23 - Jul 24
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (288 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 $199
CA $437 total
includes taxes & fees
Jul 26 - Jul 27
Streamside Cottage Half Mile to Town 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, (24 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 $252
CA $501 total
includes taxes & fees
Jul 23 - Jul 24
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior

Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
The price is CA $337
CA $712 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 2-bedroom cottage in enchanting Catskill Mountains
Exterior

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

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.6 out of 10, Exceptional, (17 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
The price is CA $237
CA $500 total
includes taxes & fees
Aug 18 - Aug 19
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
House (3 Bedrooms) | Front of property

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
The price is CA $427
CA $833 total
includes taxes & fees
Jul 27 - Jul 28
Sleepy Hollow Lake Home w/ Deck, Pool Access!
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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

8/10 Good
"Nice clean and new. Stayed here in 2022 though and the property hasn’t been as well maintained over the last few years. Good option for the area though."
Justin 1-night trip
Posted 12 hours ago
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Find out more about Windham

Windham Cottages information

Number of reviews
330
Accommodation
190 Cottages
Lowest Price
CA $437
Highest Price
CA $833

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $437 and CA $833 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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