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Search results; Over 1,000 homes in Windham

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Guest favourite
Home in Windham
Cozy Catskills Escape w/Hot Tub & Firepit
4 bedrooms, 6 beds, 2.5 private bathrooms
27 Oct – 1 Nov
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4.89 out of 5 average rating, 145 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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Home in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
6 bedrooms, 6 beds, 3 bathrooms
1–6 Oct
4.91 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Chalet in Windham
Stargazing Dome|Sauna|Firepit|HotTub|Pet Frndly
5 bedrooms, 9 beds, 4.5 bathrooms
17–22 Oct
4.98 out of 5 average rating, 100 reviews
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Top guest favourite
Home in Windham
EAT, DRINK, PLAY ... and Relax in Windham
5 bedrooms, 8 beds, 3 bathrooms
1–6 Oct
4.95 out of 5 average rating, 63 reviews
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Guest favourite
Apartment in Windham
Slope Side Luxe | Views, Decks, Walk to Mtn & Town
5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Oct
4.98 out of 5 average rating, 45 reviews
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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, 10 reviews
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Top guest favourite
Home in Windham
Walk to town | 2 Mins to Ski | Windham Mill House
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
4.98 out of 5 average rating, 87 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
1–6 Oct
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Home in Hensonville
Spacious Townhome for an Upstate getaway!
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Townhouse in Windham
Windham Mountain Village 2 bedroom townhouse
3 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
4.91 out of 5 average rating, 138 reviews
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Top guest favourite
Home in Windham
Small house, Windham, NY
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 238 reviews
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Guest favourite
Townhouse in Windham
Cheerful and Cozy 2 bedroom home in Windham
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 63 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
4–9 Oct
4.98 out of 5 average rating, 197 reviews
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Superhost
Apartment in Windham
WindhamWay MainSTREET Retreat*5 min to the Slopes
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Windham
1854 Victorian Inn - Simple Lodging - 5 BR, 5 Bath
5 bedrooms, 7 beds, 5 bathrooms
4–9 Oct
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Top guest favourite
Chalet in Windham
Velvet Timber Haus | HotTub, Sauna, Firepit, Games
7 bedrooms, 11 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Hensonville
Mountain-Modern 5BR Home • Windham & Hunter • EV
5 bedrooms, 8 beds, 3 bathrooms
19–24 Oct
4.93 out of 5 average rating, 109 reviews