Search Holiday Rentals in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 holiday 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 3.903.664 ₫
5.325.420 ₫ 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 11.003.421 ₫
13.909.966 ₫ total
includes taxes & fees
18 Nov - 19 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 3.719.105 ₫
4.165.398 ₫ total
includes taxes & fees
18 Nov - 19 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 7.098.942 ₫
7.666.856 ₫ 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 1.913.566 ₫
3.080.813 ₫ 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 8.629.152 ₫
18.131.749 ₫ total
includes taxes & fees
15 Nov - 16 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.
View all properties

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Windham Hotel Reviews

A wooden cabin interior with a bed, a desk, a television, and a large window.
Hotel Mountain Brook

Hotel Mountain Brook

Hotel Mountain Brook
Tannersville

10/10 Excellent

Great staff, breakfast, beautiful and clean
United Kingdom
Eban
Reviewed July 29, 2026
Hotel Mountain Brook

Frequently Asked Questions

Can I find holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing 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 coffee shops.

How many holiday rentals are there in Windham?

With 139 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.