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Search results; Over 1,000 homes in Windham

Home in Windham
The Lost Toboggan
3 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
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4.83 out of 5 average rating, 70 reviews
Home in Windham
Renovated Mountain House - Barrel Sauna & Fire Pit
4 bedrooms, 5 beds
18–23 Oct
New place to stay
Top guest favourite
Chalet in Windham
Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly
5 bedrooms, 9 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 99 reviews
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds
15–20 Sept
New place to stay
Top guest favourite
Cabin in Windham
Aframe Escape | Hot tub | Movie Room | Karaoke
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 59 reviews
Guest favourite
Cabin in Windham
Cozy Family-Friendly A-Frame - Windham with AC
4 bedrooms, 5 beds
15–20 Sept
4.96 out of 5 average rating, 24 reviews
Guest favourite
Townhouse in Windham
Mill House 2 | 3BD + 3.5 Bath Catskills Retreat
3 bedrooms, 5 beds
15–20 Sept
4.92 out of 5 average rating, 78 reviews
Guest favourite
Home in Windham
Catskill Villa | 6BDRM, Pool, Hot Tub & Movie Room
6 bedrooms, 8 beds
15–20 Sept
4.95 out of 5 average rating, 109 reviews
Luxe
Cabin in Windham
NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym
5 bedrooms, 8 beds
15–20 Sept
5.0 out of 5 average rating, 45 reviews
Superhost
Home in Windham
“Ski/Hike/Mtn Bike out the door Trailside Chalet”
4 bedrooms, 8 beds
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Chalet in Windham
Velvet Timber Haus | HotTub, Sauna, Firepit, Games
7 bedrooms, 11 beds
4–9 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Windham
Hot Tub · Fire pit · Pond · Minutes to Windham
4 bedrooms, 7 beds
6–11 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Hensonville
Spacious Townhome for an Upstate getaway!
2 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Apartment in Windham
Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub
4 bedrooms, 7 beds
22–27 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Chalet in Windham
Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm
5 bedrooms, 9 beds
20–25 Sept
4.98 out of 5 average rating, 174 reviews
Guest favourite
Apartment in Windham
Luxury Ski in Ski out Condo + Amenities
3 bedrooms, 6 beds
15–20 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Apartment in Windham
Slope Side Luxe | Views, Decks, Walk to Mtn & Town
5 bedrooms, 8 beds
15–20 Sept
4.98 out of 5 average rating, 45 reviews
Superhost
Rooms in Windham
Windham Cottage- Beaver Room
2 bedrooms, 3 beds
17–22 Sept
5.0 out of 5 average rating, 3 reviews