House vacation rentals in Windham County
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Top-rated house rentals in Windham County
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windham County house rentals
House rentals with a pool
Home in Wilmington
4.88 out of 5 average rating, 150 reviewsAdams Farm-"The Little Farmhouse"
Sep 29 – Oct 6
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
Jan 16 – 23
Home in Peru
4.92 out of 5 average rating, 139 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
Sep 18 – 25
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Jan 31 – Feb 7
Home in Wardsboro
5.0 out of 5 average rating, 11 reviewsSheldon Hill Chalet | 4BR Home by Mt Snow/Stratton
Nov 6 – 13
Home in Wilmington
4.9 out of 5 average rating, 20 reviewsMountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow
Oct 15 – 22
Home in Dover
5.0 out of 5 average rating, 19 reviewsSpring getaway@Mt snow, West Dover VT
Oct 18 – 25
Home in Wardsboro
5.0 out of 5 average rating, 30 reviewsMt Snow/Stratton Getaway w/Hot Tub, Fire Pit + AC!
Dec 7 – 14
Weekly house rentals
Home in Wilmington
4.99 out of 5 average rating, 171 reviewsVermont Sugar House Retreat
Jul 10 – 17
Home in Wilmington
4.94 out of 5 average rating, 241 reviewsWilmington. Easy walk to center of town.
Jul 30 – Aug 6
Home in Brattleboro
4.94 out of 5 average rating, 100 reviewsSpacious Brattleboro home on river, walk to town
Sep 22 – 29
Home in Grafton
4.92 out of 5 average rating, 186 reviewsRetro Modern Barn Apartment
Nov 8 – 15
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Sep 13 – 20
Home in Putney
4.85 out of 5 average rating, 233 reviewsPreston’s Pond-Beautiful home on Tranquil Hilltop
Dec 29 – Jan 5
Home in South Londonderry
4.85 out of 5 average rating, 100 reviewsLovers Honey Pond Treehouse with hot tub & sauna
Mar 31 – Apr 7
Home in Jamaica
4.96 out of 5 average rating, 158 reviewsCozy Riverfront Home in beautiful Jamaica
Aug 7 – 14
Private house rentals
Home in Windham
4.95 out of 5 average rating, 77 reviewsArtistic Southern Vt Countryside Home at Windham
May 7 – 14
Home in Jamaica
5.0 out of 5 average rating, 26 reviews2-Bedroom Home, 7 Minutes From Stratton Mountain
Apr 16 – 23
Home in Townshend
4.96 out of 5 average rating, 73 reviewsCozy, Comfy Country Home in Southern VT Village
Aug 22 – 29
Home in Jamaica
4.89 out of 5 average rating, 65 reviewsThe Post Haus: one-of-a-kind modern VT experience
Nov 29 – Dec 6
Home in Chesterfield
4.92 out of 5 average rating, 86 reviewsGoverner's Brook Camp - 2 Bedroom
Jun 16 – 23
Home in West Brattleboro
4.96 out of 5 average rating, 67 reviewsPrivate Brookside Farmhouse
Apr 24 – May 1
Home in Whitingham
4.97 out of 5 average rating, 61 reviewsGorgeous farmhouse beautiful view pond/mountains
Sep 29 – Oct 6
Home in Newfane
4.96 out of 5 average rating, 76 reviewsClark Farm-2 Master-Suites, Great kitchen, views!
May 11 – 18
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