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Our top choices for Windham County cottages
1. The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
The Cairn, 1840s Cozy Stone Cottage, Pet FriendlyChester
10.0 out of 10, Exceptional, (27 reviews)
"Even prettier than pictured. Very comfortable and dog-friendly. We enjoyed staying here and liked how old-fashioned it was, while still being comfortable and easy to navigate."
Katharine H.
2. Forest cottage near Lake Raponda with sunroom, gas fireplace and firepit
Forest cottage near Lake Raponda with sunroom, gas fireplace and firepitWilmington
8.6 out of 10, Excellent, (79 reviews)
"The place itself is hard to find but the host was super personable and answered immediately. Really cute cabin! Good for a few day stay."
Arianna K.
3. Rare new Home on Lake Whitingham. Semi-priv beach
Rare new Home on Lake Whitingham. Semi-priv beachWilmington
10.0 out of 10, Exceptional, (9 reviews)
"Clean, quiet and so very peaceful. Exactly what we needed. Thank you for the beautiful escape."
Anonymous traveller
4. Vermont Country Cottage (Near Village)
Vermont Country Cottage (Near Village)Londonderry
9.4 out of 10, Exceptional, (14 reviews)
"Convenient location for the event and places we wanted to visit!"
Joe A.
5. West Dover Home - 3 Miles to Mount Snow Resort!
West Dover Home - 3 Miles to Mount Snow Resort!West Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, spacious, huge back yard. Close to everything you need. Hoping to return soon!!"
Jacqueline
6. 4 Mi to Lake Raponda! Secluded Family Cottage
4 Mi to Lake Raponda! Secluded Family CottageBrattleboro
7. Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. SnowNewfane
9.6 out of 10, Exceptional, (76 reviews)
"Great location for exploring the area. The cabin is private, without feeling isolated, and had everything we needed to enjoy our 3-night stay."
Ed E.
8. 4 Mi to Lake Raponda! Secluded Family Cottage
4 Mi to Lake Raponda! Secluded Family CottageWilmington
9. Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OKJamaica
10.0 out of 10, Exceptional, (4 reviews)
"Nice and cozy, just like the listing shows. Great host. "
Kytalia B.
10. 'mount Pine' Winter Escape Near the Green Mtns!
'mount Pine' Winter Escape Near the Green Mtns!Wardsboro
10.0 out of 10, Exceptional, (1 review)
"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."
Alexander
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.