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Search results; Over 1,000 homes in Windham

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Guest favourite
Apartment in Windham
Luxury 5 * Ski-in Ski-out @ Whisper Creek
3 bedrooms, 6 beds, 3 private bathrooms
16–21 Sept
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5.0 out of 5 average rating, 11 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
27 Sept – 2 Oct
4.98 out of 5 average rating, 100 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
Luxury Windham Retreat | Hot tub + Speakeasy
5 bedrooms, 8 beds, 5.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 4 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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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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Chalet in Windham
Windham Peak Chalet
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Sept
New place to stay
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Guest favourite
Cabin in Windham
Cozy Family-Friendly A-Frame - Windham with AC
4 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
4.96 out of 5 average rating, 24 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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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
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
Townhouse in Windham
Secluded and Scenic Large Townhouse
3 bedrooms, 7 beds, 2.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 53 reviews
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Superhost
Home in Windham
“Ski/Hike/Mtn Bike out the door Trailside Chalet”
4 bedrooms, 8 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 4 reviews
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Luxe
Cabin in Windham
NEW Modern Cabin 8 mins from Skiing-Hot Tub & Gym
5 bedrooms, 8 beds, 4 bathrooms
16–21 Sept
5.0 out of 5 average rating, 45 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
18–23 Sept
4.99 out of 5 average rating, 70 reviews
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Home in Windham
1854 Victorian Inn - Simple Lodging - 5 BR, 5 Bath
5 bedrooms, 7 beds, 5 bathrooms
20–25 Sept
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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
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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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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