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Search results; Over 1,000 homes in Windham

Holiday home in Windham
Luxurious 4 BR Condo at Windham Mountain Resort
4 bedrooms, 8 beds, 4 private bathrooms
6–11 Sept
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Top guest favourite
Chalet in Windham
Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 96 reviews
Top guest favourite
Cabin in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.98 out of 5 average rating, 193 reviews
Guest favourite
Apartment in Windham
Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub
4 bedrooms, 7 beds, 4 bathrooms
6–11 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Cabin in Windham
Aframe Escape | Hot tub | Movie Room | Karaoke
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 53 reviews
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Home in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
6 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
4.91 out of 5 average rating, 32 reviews
Guest favourite
Townhouse in Windham
Mill House 2 | 3BD + 3.5 Bath Catskills Retreat
3 bedrooms, 5 beds, 3.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 77 reviews
Top guest favourite
Home in Windham
Small house, Windham, NY
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 237 reviews
Guest favourite
Townhouse in Windham
Cheerful and Cozy 2 bedroom home in Windham
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 61 reviews
Guest favourite
Home in Windham
Modern Cozy Townhome in Windham
2 bedrooms, 3 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Windham
The Mad Brook House | Walk to Main St, Windham
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Farm stay in Conesville
6 Bedroom 1860 Farmhouse Mountain Views Windham
6 bedrooms, 7 beds, 2 bathrooms
14–19 Sept
4.99 out of 5 average rating, 108 reviews
Superhost
Home in Windham
“Ski/Hike/Mtn Bike out the door Trailside Chalet”
4 bedrooms, 8 beds, 3 bathrooms
5–10 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Windham
Hot Tub · Fire pit · Pond · Minutes to Windham
4 bedrooms, 7 beds, 2 bathrooms
6–11 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Windham
River & Golf Mountain Retreat
4 bedrooms, 5 beds, 4 bathrooms
7–12 Sept
5.0 out of 5 average rating, 87 reviews
Guest favourite
Home in Hensonville
Spacious Townhome for an Upstate getaway!
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Windham
EAT, DRINK, PLAY ... and Relax in Windham
5 bedrooms, 8 beds, 3 bathrooms
14–19 Sept
4.95 out of 5 average rating, 62 reviews
Luxe
Cabin in Windham
NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym
5 bedrooms, 8 beds, 4 bathrooms
5–10 Sept
5.0 out of 5 average rating, 44 reviews