Holiday Homes in Windham

    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
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Windham and around

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

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

10.0 out of 10, Exceptional, (49)
"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
Property grounds

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 €177
includes taxes & fees
19 Aug - 20 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Beautiful, private Property/swimming pond
Interior

Beautiful, private Property/swimming pond

9.6 out of 10, Exceptional, (72)
"We had an amazing stay at this home during our family ski trip. The house was spacious, clean, and perfectly located near the slopes. The host was responsive and made sure we had everything we needed. We would definitely stay here again—highly recommend for a relaxing and fun ski getaway."
Beautiful, private Property/swimming pond
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
Terrace/patio

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 €645
includes taxes & fees
25 Aug - 26 Aug
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Fridge, microwave, oven, stovetop

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 €300
includes taxes & fees
8 Sept - 9 Sept
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (5)
"We had a 2 night stay while in Catskill for a wedding. My hubby, 8 year old and 2 dogs in tow. House was just right for us. My son loved the board games available and the foosball table. House is uncluttered and very clean. Surrounding are is historic with a short walk to downtown shops. I would definitely rent here again. "
Charming Catskill getaway walking distance to Main St. Pet-friendly!
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
Fridge, microwave, oven, stovetop

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
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub
Fridge, microwave, oven, stovetop

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

9.8 out of 10, Exceptional, (75)
"Very relaxing, well equipped home. Hot tub was fantastic. Kitchen fully stocked with pots, pans, cooking and eating utensils. "
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
A heated pool

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!Spring Special3rd night half OFF!” W/weekend
Terrace/patio

Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend

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!Spring Special3rd night half OFF!” W/weekend
The Catskills Red Barn-near Belleayre
Property grounds

The Catskills Red Barn-near Belleayre

10.0 out of 10, Exceptional, (47)
"Blythe is super helpful. We had a fantastic night in the cabin, which had so much character. Belleayre is so close, it’s a great little getaway to go and have some fun. "
The Catskills Red Barn-near Belleayre
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Terrace/patio

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 €350
includes taxes & fees
9 Sept - 10 Sept
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Beautiful new house 3/4 mile from Hunter Mountain
Exterior

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.
Fridge, microwave, oven, stovetop

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! 3rd night 1/2 price w/weekend
Fridge, microwave, oven, stovetop

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

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! 3rd night 1/2 price w/weekend
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Exterior

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

10.0 out of 10, Exceptional, (113)
"Amazing Woodstock location!"
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Country Home with Private Swimming Pond and Beautiful Mountain Views
Outdoor dining

Country Home with Private Swimming Pond and Beautiful Mountain Views

10.0 out of 10, Exceptional, (117)
"The view is absolutely stunning! "
Country Home with Private Swimming Pond and Beautiful Mountain Views
Catskill Country House w/ Hot Tub Near Hiking
Dining

Catskill Country House w/ Hot Tub Near Hiking

9.6 out of 10, Exceptional, (13)
"Another great stay"
The price is €349
includes taxes & fees
19 Aug - 20 Aug
Catskill Country House w/ Hot Tub Near Hiking
A world where time stands still, close to Belleayre Ski & Wedding venues.
Fridge, microwave, oven, stovetop

A world where time stands still, close to Belleayre Ski & Wedding venues.

9.6 out of 10, Exceptional, (18)
"We had the perfect weekend getaway—quiet, serene and comfy. The house was beautifully furnished and the outdoor space gave incredible views of the landscape. Highly recommend!"
The price is €470
includes taxes & fees
18 Aug - 19 Aug
A world where time stands still, close to Belleayre Ski & Wedding venues.
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
Interior

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
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 Windham Hotel Reviews

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Great location. Beautiful resort. Great and helpful staff"
Shirley 2-night trip
Posted 11 hours ago
Hunter Lodge, a Bluebird by Lark