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

Search Windham Cottage Rentals from CA $495

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Windham cottages

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 $255
CA $507 total
includes taxes & fees
Jul 23 - Jul 24
Charming Cottage in the Heart of Catskill & Pet Friendly
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 $223
CA $495 total
includes taxes & fees
Aug 3 - Aug 4
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
The price is CA $340
CA $717 total
includes taxes & fees
Jul 13 - Jul 14
Cozy 2-bedroom cottage in enchanting Catskill Mountains
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 $508
CA $803 total
includes taxes & fees
Jul 13 - Jul 14
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
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 $429
CA $837 total
includes taxes & fees
Jul 19 - Jul 20
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"Loved the pool, the hot tubs, the sauna and the steamroom. Great staff, nice room, lovely location!"
Eniko 2-night trip
Posted 6 hours ago
Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Windham

Windham Cottages information

Number of reviews
42
Accommodation
190 Cottages
Lowest Price
CA $495
Highest Price
CA $837

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between CA $495 and CA $837 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.

Explore a world of travel with Expedia