Windham 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

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Recent Windham guest reviews

We had a good stay here! The house itself is gorgeous, bedrooms and bathrooms were very nice and all the amenities/appliances were top quality. The pool was great and kids enjoyed a lot. Overall we had a mix group of people/kids (ranging from 2 years to 16 years). I will say its definitely better for the older kids and not as baby-proofed for toddlers (open stairs, open concept, all doors are easy handles to open so we really had to watch the little ones.) Outside the grass is all really long, ground is rocky, and there are cliffs/ditches, so when we took the kids outside, we had to be SUPER alert to make sure no one fell and got severely injured. There were a couple things we'd like to call out: 1. Hospitality could have been a little better - we did not hear from the owners all weekend and had to reach out multiple times to help get the wifi and also make them aware of dirty towels, garbage not taken out, etc that we found when we got there. There were also amenities listed (iron/board/hair dryer) on the listing that we did not find or see anywhere in the house. The owners were responsive though which was nice. 2. For the Pool, there was a safety concern which is the door not having a lock on it from the outside. Having little kids with us, this was daunting all weekend. Since the house is advertised to be family/kids oriented, the pool door should definitely have a lock so kids can't go into it unsupervised. 3. There are two 3.5 feet deep ditches next to the driveway on both sides that 3 of our cars went straight into because it is not clearly visible when driving up. We broke our car bumpers on it and will need repairs. While we understand that is our fault, we wish that was something the owners had shared with us to be mindful of in advance so we'd have known to look out for it.
Amal . | Jul 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. 47 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.

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24/7 guest service
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Seamless check-in
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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.