Windham Vacation Rentals

Compare 19 vacation rentals.
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Make Windham your next getaway

Nestled in the northern Catskill Mountains of Greene County, just two hours from New York City, Windham is the Catskills' coolest mountain village—a four-season escape with real ski slopes, a celebrated arts scene, farm-to-table dining, and an effortlessly welcoming energy that draws city dwellers looking for exactly what Windham quietly delivers. 

Top Windham property types

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Apartments

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House rentals

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Villas

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Popular amenities for Windham vacation rentals

Popular
Dog-friendly Hot tub Internet
Mtn-View Home w/ Deck on 4 Acres in Windham
3 Bedroom | 2 Bath | Sleeps 6

Mtn-View Home w/ Deck on 4 Acres in Windham - Windham, NY

$212 avg / night
(excludes fees and taxes)
Relaxing Catskills Apt < 3 Mi to Windham Mountain!
2 Bedroom | 2 Bath | Sleeps 7

Relaxing Catskills Apt < 3 Mi to Windham Mountain! - Windham, NY

$264 avg / night
(excludes fees and taxes)
Custom Windham Mtn Villa w/ Pool, Theater & Views!
5 Bedroom | 4.5 Bath | Sleeps 16

Custom Windham Mtn Villa w/ Pool, Theater & Views! - Windham, NY

$1,351 avg / night
(excludes fees and taxes)
4.0 (1)
Homey Windham Condo: Hike & Ski the Catskill Mtns!
2 Bedroom | 1 Bath | Sleeps 4

Homey Windham Condo: Hike & Ski the Catskill Mtns! - Windham, NY

$208 avg / night
(excludes fees and taxes)
4.0 (1)
Spacious Apt w/ Yard: 3 Mi to Windham Mountain
2 Bedroom | 2 Bath | Sleeps 6

Spacious Apt w/ Yard: 3 Mi to Windham Mountain - Windham, NY

$237 avg / night
(excludes fees and taxes)
1.0 (1)

View 14 more homes

Recent Windham guest reviews

We had a wonderful stay. The supplies of coffee and tea bags served our needs opulently. The place was neat and clean. Only problem was the smelly tap water - nothing can be done about it - for it is the type of well water we get there at Windham, NY. Even in restaurant in Downtown Windham we faced the same problem, we had to buy the bottle waters. Future visitors to this neat place may choose to bring their own bottle water. There was a Brita Water Filter which we did not use. The owner were extremely helpful. The only handicap was that the photographs made the place look a lot bigger than what it is. We'll definitely revisit the place should the opportunities arise.
Dr. T. | May 2025
Place was clean and convenient for skiing! Note - although it is 1/2 mile to Windham Mtn - we skied Hunter Mountain which was only 15-20 min drive. It is a perfect place to be able to walk to dinner both nights and avoid drinking and driving. Great stay! I would definitely stay here again!
Craig . | Feb 2025
I’ve stayed at many short term rental properties over the years and this one was one of the best! The home was clean and well kept. The host was communicative and easy to work with.
Troy . | Nov 2024
Windham vacation rental FAQ

Yes, 7 of our Windham homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 53 of our Windham vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Windham vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Windham team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Windham, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Whatever the season brings, this small Catskills town makes the most of it.

What you'll love about Windham

Windham Mountain Club's 54-trail ski area and year-round resort amenities give the village a genuine activity anchor in every season—skiing and snowboarding in winter, golf and mountain biking when the snow melts. Windham Fine Arts represents over 65 artists in a 3,000-square-foot gallery that's well above what most Catskill towns offer. 

The surrounding northern Catskills—Kaaterskill Falls, Colgate Lake, legendary trout streams, and Hunter Mountain nearby—give Windham a natural backdrop that rewards exploration beyond the village itself.

Fun things to do

Local tips

Catskills skiing, art, and two hours from Manhattan

Windham is the Catskills at their most complete. A genuine ski mountain just two hours from New York City and utterly disconnected from it, Windham delivers exactly what city-dwellers are actually looking for. Book your vacation rental and get ready to unplug.