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
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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"
May 2 – 9
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
Oct 16 – 23
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Jan 27 – Feb 3
Home in Peru
4.92 out of 5 average rating, 139 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
Feb 21 – 28
Home in Wardsboro
5.0 out of 5 average rating, 11 reviewsSheldon Hill Chalet | 4BR Home by Mt Snow/Stratton
Nov 22 – 29
Home in Wilmington
4.77 out of 5 average rating, 13 reviewsChimney Hill Retreat w/ Amenity Center & Fireplace
May 16 – 23
Home in Wardsboro
5.0 out of 5 average rating, 30 reviewsMt Snow/Stratton Getaway w/Hot Tub, Fire Pit + AC!
Oct 25 – Nov 1
Home in Wilmington
4.9 out of 5 average rating, 20 reviewsMountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow
Mar 2 – 9
Weekly house rentals
Home in Wilmington
4.94 out of 5 average rating, 241 reviewsWilmington. Easy walk to center of town.
Aug 17 – 24
Home in Wilmington
4.99 out of 5 average rating, 171 reviewsVermont Sugar House Retreat
Oct 2 – 9
Home in Grafton
4.92 out of 5 average rating, 186 reviewsRetro Modern Barn Apartment
Nov 5 – 12
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
Jan 3 – 10
Home in Jamaica
4.96 out of 5 average rating, 158 reviewsCozy Riverfront Home in beautiful Jamaica
Aug 4 – 11
Home in Jamaica
4.84 out of 5 average rating, 232 reviewsHistoric 1832 Parker House ~ Sleeps 10, Pool Table
Oct 14 – 21
Home in Brattleboro
4.94 out of 5 average rating, 100 reviewsSpacious Brattleboro home on river, walk to town
Sep 2 – 9
Private house rentals
Home in Town of Rockingham
4.89 out of 5 average rating, 113 reviewsBeautiful Home in the Mountains - The Fox & Owl
Jul 2 – 9
Home in Brattleboro
4.91 out of 5 average rating, 170 reviewsCozy Cabin Retreat on the River
Mar 20 – 27
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
Jul 15 – 22
Home in Windham
4.95 out of 5 average rating, 77 reviewsArtistic Southern Vt Countryside Home at Windham
May 27 – Jun 3
Home in Wardsboro
4.82 out of 5 average rating, 11 reviewsThe Perch
Jun 5 – 12
Home in Townshend
4.96 out of 5 average rating, 73 reviewsCozy, Comfy Country Home in Southern VT Village
Aug 19 – 26
Home in Chesterfield
4.95 out of 5 average rating, 41 reviewsThe River House
Oct 14 – 21
Home in West Brattleboro
4.96 out of 5 average rating, 67 reviewsPrivate Brookside Farmhouse
Apr 21 – 28
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