Holiday Homes in Windham

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

This weekend

Featured Holiday Homes in Windham and around

Property grounds
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
10.0 out of 10, Exceptional, (105)
"Great location. Comfortable space. The only drawback was the downstairs bedroom mattress."
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
Exterior
Last minute deal!! Scandinavian BBQ hut and Hot tub
10.0 out of 10, Exceptional, (54)
"We enjoyed our stay. Having so many outdoor things was great (fire pit, the bbq house, she shed, hot tub). It was a close drive to Hunter and Windham for skiing and dining out. The kitchen was also well stocked with pots, pans etc."
Last minute deal!! Scandinavian BBQ hut and Hot tub
Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is €1,582
per night
12 May - 13 May
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Save an average of 15% on thousands of hotels when you're signed in
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Fridge, microwave, oven, stovetop
Your peaceful, private retreat to get away with friends & family!
10.0 out of 10, Exceptional, (22)
"The place and host were amazing. The property was well kept and well appointed for our stay. It is nicely secluded, and the hot tub was perfect for relaxing."
Your peaceful, private retreat to get away with friends & family!
Exterior
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
10.0 out of 10, Exceptional, (1)
"🙂"
The price is €241
per night
7 May - 8 May
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (250)
"Very clean, and the little things really made a difference: nice sheets, shampoo and soap provided, quality towels. We would stay here again for sure."
The price is €737
per night
5 May - 6 May
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Living area
Beautiful Hudson Valley Woodland Retreat with Swimming Pool. Pets welcome.
10.0 out of 10, Exceptional, (20)
"Excellent host and home, with everything exactly as pictured and described, looking forward to booking another stay here again."
Beautiful Hudson Valley Woodland Retreat with Swimming Pool. Pets welcome.
Exterior
Woodstock walk to town, entire home and property to yourself, mountain views.
10.0 out of 10, Exceptional, (12)
"Perfect combo of new and old-we would stay here again in a heartbeat. Would love to take advantage of the deck/patio next time when its not so cold!"
Woodstock walk to town, entire home and property to yourself, mountain views.
Exterior
The 212 Escape
10.0 out of 10, Exceptional, (2)
"Super house - very spacious and clean. We had a great stay!"
The 212 Escape
Snow and ski sports
Woodstock House on 35 private acres Mtn Views
10.0 out of 10, Exceptional, (35)
"Perfect long weekend getaway for our family of four plus our dog. Plenty of room both inside and out. Close to skiing, hikes, and nearby towns, Woostock, Phoenicia, etc. Thank you!"
Woodstock House on 35 private acres Mtn Views
Property grounds
Birch Creek Retreat ~ Rustic & Secluded ~ 8br, 8ba 3min Lake+Ski, NEW SAUNA!
10.0 out of 10, Exceptional, (82)
"This was a return winter visit for our family. We love this property with its walking trails and other outside amenities. Plus the house is large enough for our family of ten to not get in each others hair. The kitchen is great and well stocked with glasses, dishes, pots and pans as we cook dinner as a family every night. We explored some towns this time and enjoyed the area. And of course, I need to include, that gem of a ski mountain, Belleayre. just down the street.. Other than wanting more...
Birch Creek Retreat ~ Rustic & Secluded ~ 8br, 8ba 3min Lake+Ski, NEW SAUNA!
Fridge, oven, stovetop, dishwasher
Birch Creek Mountain House- 3 minutes to Belleayre Mtn
10.0 out of 10, Exceptional, (52)
"The property is perfect,2 min away from Bellayre ski center ,it is nice and clean very large house and exactly as described. 5 stars."
Birch Creek Mountain House- 3 minutes to Belleayre Mtn
Fridge, microwave, stovetop, coffee/tea maker
Modern-Chic Athens Home - Fish, Ski & Swim!
10.0 out of 10, Exceptional, (6)
"2nd time we stayed hear. Great place! We hope to go back again. It is near Hudson. NY where our family members were born and raised."
Modern-Chic Athens Home - Fish, Ski & Swim!
Exterior
Cozy Country Farmhouse Along the Catskill Scenic Trail
10.0 out of 10, Exceptional, (104)
"We had the best time! The house was clean with comfy beds, it had all the basic supplies we needed, and had a few fun games to play and interesting books to read during the evenings. The views were beautiful and we enjoyed exploring/walking on the property. The house was close to the bookstores in Hobart as well as delicious local restaurants. The Rich Farm farmhouse was a great place to stay. 😊"
The price is €305
per night
15 May - 16 May
Cozy Country Farmhouse Along the Catskill Scenic Trail
Aerial view
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
9.8 out of 10, Exceptional, (66)
"We just needed a place to relax and recharge for a few days and this house was perfect for us and our teenage son, who enjoyed skiing at Hunter and exploring the grounds with our dog. The house had everything we needed."
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
2 bedrooms, free WiFi, bed sheets
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
9.8 out of 10, Exceptional, (17)
"A friend and I visited for a final push on our doctoral dissertations. The immaculate and modern space provided a perfect atmosphere for that hard work! The sauna, which is professional grade was rejuvenating. Incredibly thoughtful setup in terms of heat and light controls. The Murphy bed was so comfortable. Has it all - aesthetics and comfort. Nearby grocery store well stocked! Will come back with my wife!"
The price is €332
per night
7 May - 8 May
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Property grounds
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
9.8 out of 10, Exceptional, (80)
"Natalya was a great host! Property was very nice and great location to Hunter!"
The price is €603
per night
5 May - 6 May
THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
Smart TV, fireplace, DVD player, table football
Catskill Mountain Getaway - minutes to Hunter and Windham Mtns., jucuzzi,
9.8 out of 10, Exceptional, (133)
"This was a really nice spot for a group of friends to have a nice chill and fun stay that was conveniently located near multiple ski mountains."
Catskill Mountain Getaway - minutes to Hunter and Windham Mtns., jucuzzi,
Microwave, coffee/tea maker, cookware/dishes/utensils
Cozy cabin with great views and fire place!
9.8 out of 10, Exceptional, (72)
"This place with everything we hoped it would be and then some. Hosts were easily accessible. The whole hog theme of the cabin was a great touch. We were there to hike and found a ton of trails in the area. We would definitely stay again and recommend this place to anyone."
Cozy cabin with great views and fire place!
Don't see what you're looking for?
See all available properties in Windham
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.

Other property types in Windham

Property grounds
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is €1,582
per night
12 May - 13 May
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Exterior
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
10.0 out of 10, Exceptional, (1)
"🙂"
The price is €241
per night
7 May - 8 May
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
1 bedroom, Internet, bed sheets
Hotel Woodstock - Iris suite
9.6 out of 10, Exceptional, (45)
"Cool propertry in a unique town"
The price is €211
per night
9 May - 10 May
Hotel Woodstock - Iris suite
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.

Windham Holiday Homes information

Number of reviews
1,047
Accommodation
593 Holiday Homes
Lowest Price
€241
Highest Price
€1,587

Recent Reviews in Windham
Expedia verified reviews