East Windham Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select East Windham Vacation Homes

Cozy year round retreat! Close to skiing, hiking and swimming.
Relax on the covered deck with Adirondack chairs, a table, and a grill for outdoor cooking.

Cozy year round retreat! Close to skiing, hiking and swimming.

10.0 out of 10, Exceptional, (48)
"Summer in the Catskills is a treat and these are the accommodations to enjoy it to its fullest. Can’t wait to stay again!"
Cozy year round retreat! Close to skiing, hiking and swimming.
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Relax on the deck with Adirondack chairs overlooking a serene landscape.

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.0 out of 10, Wonderful, (48)
"Great for in town stays"
The price is CA $155
CA $277 total
includes taxes & fees
Aug 11 - Aug 12
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
Relax in a serene outdoor hot tub area surrounded by trees and a deck.

Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

9.8 out of 10, Exceptional, (78)
"Location is great; close to a lot of hiking opportunities and right in the middle of breathtaking scenery. The house was clean and provided excellent accomodations."
The price is CA $557
CA $972 total
includes taxes & fees
Aug 10 - Aug 11
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, gas stove, and wooden cabinets.

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

2.0 star property
8.8 out of 10, Excellent, (17)
"Thank you so much for an amazing stay"
The price is CA $206
CA $475 total
includes taxes & fees
Aug 12 - Aug 13
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Enjoy cooking in this well-lit kitchen with a central island and modern appliances.

Charming Catskill getaway walking distance to Main St. Pet-friendly!

10.0 out of 10, Exceptional, (3)
"We had a great stay here! The check in process was super easy and Jiyon was very communicative. The house was super comfortable and conveniently located for a weekend of hiking. Would definitely stay here again!"
Charming Catskill getaway walking distance to Main St. Pet-friendly!
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
Enjoy cooking in this well-lit kitchen with a central island and stainless steel appliances.

STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter

10.0 out of 10, Exceptional, (48)
"We loved our time out here and hope to be back soon!"
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
Relax by the serene pool surrounded by lush greenery and trees.

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

10.0 out of 10, Exceptional, (63)
"This was an excellent place to stay in such a beautiful area."
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
Relax in a serene outdoor setting surrounded by a mature tree and beautifully manicured lawn.

Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay

9.6 out of 10, Exceptional, (76)
"House was very clean. Property managers were very responsive to check in and check out time and anything we needed during our stay. Very close to the mountain and beautiful location. Would highly recommend."
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Relax in a hot tub on a spacious deck with stairs leading to a covered area.

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

4.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent house, very clean and great location. Host Henry was phenomenal at communicating and very helpful with any questions. Will definitely stay again."
The price is CA $179
CA $559 total
includes taxes & fees
Sep 9 - Sep 10
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Beautiful new house 3/4 mile from Hunter Mountain
Cozy cabin with a central entrance and windows on either side, set amidst a serene winter landscape.

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (130)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
Enjoy cooking in this well-lit kitchen with a large window and modern appliances.

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.8 out of 10, Exceptional, (46)
"The perfect family getaway"
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Enjoy cooking in this well-equipped kitchen with a dining area nearby.

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
2025 Log Home- Ski Chalet w/ Luxury Amenities. direct Views of Hunter Slopes
Exterior

2025 Log Home- Ski Chalet w/ Luxury Amenities. direct Views of Hunter Slopes

2025 Log Home- Ski Chalet w/ Luxury Amenities. direct Views of Hunter Slopes
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
Cozy living area with a sofa, coffee table, and dining table for four, surrounded by framed pictures and natural wood accents.

Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

10.0 out of 10, Exceptional, (43)
"Excellent log cabin home, perfect home base for a ski weekend at Windham. "
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
Escape to a serene cabin nestled in a lush forest, surrounded by a well-maintained garden and a stone pathway leading to the entrance.

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

10.0 out of 10, Exceptional, (183)
"The property was perfect! Beautiful, secluded & very welcoming "
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
Blackbear Lodge - Luxury Cabin, Kid-Friendly
Relax in this inviting living space with a comfortable sofa, exposed wooden beams, and a cozy fireplace.

Blackbear Lodge - Luxury Cabin, Kid-Friendly

10.0 out of 10, Exceptional, (4)
"We had a great stay here! Everything was comfortable and just all around easy. The location is amazing—we loved that it's tucked away and private without being so out of the way. "
Blackbear Lodge - Luxury Cabin, Kid-Friendly
New Luxuary Hunter Ski Resort&Lake Chalet, Hot Tub, Sauna, Fireplace, Mountains
Enjoy a serene lake view from the deck, surrounded by trees and distant hills.

New Luxuary Hunter Ski Resort&Lake Chalet, Hot Tub, Sauna, Fireplace, Mountains

10.0 out of 10, Exceptional, (9)
"Tons of activities in house beautiful area."
The price is CA $898
CA $1,589 total
includes taxes & fees
Aug 20 - Aug 21
New Luxuary Hunter Ski Resort&Lake Chalet, Hot Tub, Sauna, Fireplace, Mountains
Your peaceful, private retreat, escape with friends & family! Incredible views!
Cozy kitchen with a brick fireplace, wooden beams, and a large window.

Your peaceful, private retreat, escape with friends & family! Incredible views!

10.0 out of 10, Exceptional, (38)
"Clean, comfortable, well-appointed and cozy, We had a wonderful stay. We had all kinds of weather while we were there and were able to enjoy the beautiful grounds, the hot tub, the sunny front porch and the cozy living room. The beds were comfortable and the kitchen stocked with everything you might need. Will definitely be returning."
Your peaceful, private retreat, escape with friends & family! Incredible views!
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
Relax in this cozy living space with a fireplace, comfortable sofa, and flat-screen TV.

SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!

9.6 out of 10, Exceptional, (30)
"Had a great 2 night stay. Location is close to Hunter. "
SPECTACULAR Hunter Mountain Views, INCREDIBLE LOCATION-2 minutes to slopes !!
Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths AC close to everything
Experience a charming stay in a scenic setting with a welcoming porch and a large wheel feature.

Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths AC close to everything

10.0 out of 10, Exceptional, (52)
"Our family had an excellent winter getaway at this cabin. The check-in process was easy and access to the mountain and the towns made for a great stay. Highly recommend for families with multiple young children."
Best rated cabin in Hunter cozy 4 Bedrooms 3 full baths AC close to everything
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top East Windham Hotel Reviews

The Colonial Motel

The Colonial Motel

10/10 Excellent
"First time in NY and loved this stay. Even though it was one night I slept like a baby. Favorite thing was the confortable bed and pillows. Absolutely loved the sheets and cover. Truly felt at home. Plus Josh, was very friendly and made us feel really welcomed! "
Adriele 1-night trip
Posted 14 hours ago
The Colonial Motel