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

Windham Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Windham vacation rentals

A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

1. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (346 reviews)
"Everything was perfect nice and quiet and peaceful the stay there was amazing highly recommend if you want some alone time from the world🙏"
United States
Mike
The price is AED 558
AED 762 total
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Front of property

2. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (4 reviews)
"The best "
United States
Miguel
The price is AED 1,576
AED 1,992 total
includes taxes & fees
16 Nov - 17 Nov
Windham NY Escape
A wooden deck with a grill, chairs, and a potted plant.

3. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (321 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is AED 533
AED 597 total
includes taxes & fees
16 Nov - 17 Nov
Starlite Motel
A bedroom with a large window offering a view of trees and sky.

4. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is AED 1,005
AED 1,086 total
includes taxes & fees
4 Dec - 5 Dec
Gather Greene
Living area

5. Suites on Main

Suites on Main
3.0 star property
Margaretville
7.2 out of 10, Good, (82 reviews)
"You get what you pay for - cheap, not value. Spent the first 2 hours cleaning because it was barely touched - even dining table and chairs had crumbs and spill stains. The coffee maker was black inside the water compartment. I had to pick up silverware and dish soap from the dollar store because there was only 2 forks and spoons for a place advertised for 6 and no dish soap to clean dishes. I’m confident my cleaning and items I left behind for the next guests will be reimbursed by karma. Oh,...
United States
Jonathan
The price is AED 340
AED 514 total
includes taxes & fees
15 Nov - 16 Nov
Suites on Main
A covered outdoor area with wooden benches and a view of a green landscape.

6. Mtn-view Luxe Catskills Retreat for Groups

Mtn-view Luxe Catskills Retreat for Groups
3.0 star property
Hobart
The price is AED 1,234
AED 2,593 total
includes taxes & fees
22 Nov - 23 Nov
Mtn-view Luxe Catskills Retreat for Groups
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.
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Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Very clean, quiet AC, nice staff. Convenient location, easy to drive to nearby towns and hiking trails. À simple breakfast is included; good coffee all day. Quality of bedding and bath towels can be improved, but good enough for the price I paid."
Tianyu 3-night trip
Posted 8 hours ago
Hotel Vienna

Frequently asked questions

Can I find vacation rentals in Windham?

Yes, we give you a choice of vacation rentals close to top points of interest in Windham, or you can select a more remote option if you'd like a relaxing place to stay. Discover why Windham is known for its ski slopes and mountain landscape. While you're here, grab a bite or have a drink at the coffeehouses.

What are some of the best vacation rentals in Windham?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Windham is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Windham?

With 139 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What can I see and do in Windham?

Elm Ridge Wild Forest and Ashland Park are a couple of lovely local spots to get outside and enjoy nature. Windham Country Club and Windham Mountain Resort are other places to visit while you're in town.

What are vacation rentals like in Windham?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Windham. Vacation rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.