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Search results; Over 1,000 homes in Windham

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Guest favourite
Guest house in Windham
Little Bear’s Cottage Great location, cozy & cute
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.97 out of 5 average rating, 122 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, 59 reviews
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Home in Windham
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 5 reviews
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Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Sept
New place to stay
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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
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
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
Home in Windham
Pool |MTNView| HotTub |Sauna| Games|Movie| Firepit
6 bedrooms, 9 beds, 3 bathrooms
5–10 Oct
4.97 out of 5 average rating, 37 reviews
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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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Top guest favourite
Cabin in Windham
Cozy Creekside Cabin | 5 Mins to Windham Mt!
3 bedrooms, 4 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 226 reviews
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Top guest favourite
Chalet in Windham
Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm
5 bedrooms, 9 beds, 4.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 174 reviews
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Guest favourite
Home in Windham
Villa Windham | 6BDRM, Pool, Hot Tub & Movie Room
6 bedrooms, 8 beds, 3.5 bathrooms
16–21 Sept
4.95 out of 5 average rating, 109 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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Home in Windham
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
6 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
4.91 out of 5 average rating, 32 reviews
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Top guest favourite
Chalet in Windham
Mountain Chalet with Hot Tub & Pool
5 bedrooms, 8 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 80 reviews
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Top guest favourite
Cabin in Windham
Catskills Designer Retreat near Hiking + Swimming
4 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.97 out of 5 average rating, 142 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
17–22 Sept
4.98 out of 5 average rating, 87 reviews