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Search results; Over 1,000 homes in Windham

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Top guest favourite
Apartment in Windham
Hideaway Windham/Hunter Fireplace, Snow & Skiing
1 bedroom, 1 bed, 1 private bathroom
25–30 Oct
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4.9 out of 5 average rating, 258 reviews
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Home in Windham
Renovated Mountain House - Barrel Sauna & Fire Pit
4 bedrooms, 5 beds, 2.5 bathrooms
26–31 Oct
New place to stay
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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, 100 reviews
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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, 60 reviews
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Top guest favourite
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Cottage in Windham
Cozy Cottage Retreat Close to Main St/Windham Mtn
2 bedrooms, 2 king beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 70 reviews
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Superhost
Rooms in Windham
Windham Cottage- Beaver Room
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Windham
The Mad Brook House | Walk to Main St, Windham
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Windham
Small house, Windham, NY
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 237 reviews
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Top guest favourite
Cabin in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 197 reviews
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Top guest favourite
Home in Windham
EAT, DRINK, PLAY ... and Relax in Windham
5 bedrooms, 8 beds, 3 bathrooms
19–24 Sept
4.95 out of 5 average rating, 62 reviews
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Superhost
Home in Windham
“Ski/Hike/Mtn Bike out the door Trailside Chalet”
4 bedrooms, 8 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Townhouse in Windham
Mill House 2 | 3BD + 3.5 Bath Catskills Retreat
3 bedrooms, 5 beds, 3.5 bathrooms
19–24 Sept
4.92 out of 5 average rating, 78 reviews
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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
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Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Chalet in Windham
Gorgeous Lodge | Mt View, HotTub, Firepit, Game Rm
4 bedrooms, 8 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 184 reviews
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Guest favourite
Apartment in Windham
Luxury 5 * Ski-in Ski-out @ Whisper Creek
3 bedrooms, 6 beds, 3 bathrooms
19–24 Sept
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in Windham
*The View* ski in/out at Windham Mountain Resort
5 bedrooms, 15 beds, 6 bathrooms
19–24 Sept
4.93 out of 5 average rating, 28 reviews
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Guest favourite
Cabin in Windham
The Windham A
3 bedrooms, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 40 reviews