Windham Vacation Rentals

Compare 22 vacation rentals.
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Make Windham your next getaway

Explore our vacation rentals in Windham NY. Our private accommodations include everything you need to have the perfect getaway, whether you're here for a family vacation, couples retreat, or making memories with friends.

Top Windham property types

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House rentals

View 12 House rentals
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Apartments

View 9 Apartments
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Villas

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Popular amenities for Windham vacation rentals

Popular
Dog-friendly Hot tub Internet
1/2 Mi to Windham Mtn: Main Street Condo
2 Bedroom | 2 Bath | Sleeps 4

1/2 Mi to Windham Mtn: Main Street Condo - Windham, NY

$140 avg / night
(excludes fees and taxes)
5.0 (3)
Catskills Home, 5 Mins to Windham Mtn Resort!
2 Bedroom | 2 Bath | Sleeps 6

Catskills Home, 5 Mins to Windham Mtn Resort! - Windham, NY

$144 avg / night
(excludes fees and taxes)
4.5 (8)
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski
2 Bedroom | 1 Bath | Sleeps 6

Cozy Catskill Condo - 2 Mi to Windham Mountain Ski - Windham, NY

$163 avg / night
(excludes fees and taxes)
5.0 (1)
Peaceful Catskills Condo w/ Deck + Mountain View!
1 Bedroom | 1 Bath | Sleeps 2

Peaceful Catskills Condo w/ Deck + Mountain View! - Windham, NY

$179 avg / night
(excludes fees and taxes)
Slope Views: Luxe Windham Retreat w/ Hot Tub!
5 Bedroom | 3 Bath | Sleeps 17

Slope Views: Luxe Windham Retreat w/ Hot Tub! - Windham, NY

$624 avg / night
(excludes fees and taxes)
5.0 (3)

View 17 more homes

Browse more vacation rental amenities in Windham

Pool | Lake view | A/C | Washer/dryer | Balcony | Bikes | Ping-pong table | Pool table | Beach access | Kayaks

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
We had a wonderful stay at this cozy, very clean and warm home just minutes from Windham Mountain. After a long day on the slopes it was the perfect place to relax and unwind. The kitchen was well equipped and in the living room they even had a bunch of board games to choose from. The location is ideal for skiing and the home itself was welcoming and well-appointed. We will definitely stay here again! Thank you Michael!
Evelyn . | Feb 2025
Windham vacation rental FAQ

Yes, 8 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. 58 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
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Seamless check-in
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Professional cleaning

Nearby destinations

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