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

Search Windham Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windham cottages

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.
$317 nightly
The price is $355
Jul 22 - Jul 23
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly

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.
$321 nightly
The price is $347
Aug 17 - Aug 18
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Cozy 2-bedroom cottage in enchanting Catskill Mountains

Cozy 2-bedroom cottage in enchanting Catskill Mountains
Catskill
$468 nightly
The price is $506
Jul 18 - Jul 19
Total with taxes and fees
Cozy 2-bedroom cottage in enchanting Catskill Mountains

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
$518 nightly
The price is $559
Jul 19 - Jul 20
Total with taxes and fees
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

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
$548 nightly
The price is $591
Jul 19 - Jul 20
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windham Hotel Reviews

Find out more about Windham

Windham Cottages information

Number of reviews
Accommodation
Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Windham cost?
Cottages in Windham range between and 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