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Cottages in Windham County
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Our top choices for Windham County cottages

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendlyWilmington
8.6 out of 10, Excellent, (66 reviews)

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
The Cairn, 1840s Cozy Stone Cottage, Pet FriendlyChester
10.0 out of 10, Exceptional, (20 reviews)

Vermont Country Cottage (Near Village)
Vermont Country Cottage (Near Village)Londonderry
9.4 out of 10, Exceptional, (14 reviews)

Rare new Home on Lake Whitingham. Semi-priv beach
Rare new Home on Lake Whitingham. Semi-priv beachWilmington
10.0 out of 10, Exceptional, (6 reviews)

10.0 out of 10, Exceptional, (1 review)

Near Skiing & Hiking: Quiet Home in West Wardsboro
Near Skiing & Hiking: Quiet Home in West WardsboroWest Wardsboro

Hiking Trails On-site: Cozy Falls Brook Cabin
Hiking Trails On-site: Cozy Falls Brook CabinBrattleboro
10.0 out of 10, Exceptional, (2 reviews)

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!Wilmington
10.0 out of 10, Exceptional, (1 review)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham County Hotel Reviews

Hampton Inn Brattleboro
10/10 Excellent
















































































