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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.

Guest favorite
Home in Putney
Vermont Botanical Studio Apartment
This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.
Aug 18 – 25
$81 per night
Guest favorite
Home in Newfane
Peaceful cabin close to skiing & Brattleboro
Our 4BR/2BA home allows you to enjoy the best of Southern VT. Skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants nearby. Open concept space, cook's kitchen, jet bathtub, beautiful gardens, winter hot tub off deck, and large patio and fireplace give a homey feel. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat after a day exploring the best of Southern Vermont!
Jan 26 – Feb 2
$230 per night
Guest favorite
Home in Readsboro
Writers Artists Digital Nomads Sanctuary Awaits!
Spotless, quiet, home, everything you need, exclusively yours, nestled in VT's Green Mtns, babbling brook. Great location! Winter activities, antiques, shops, lakes, hike, covered bridges, cozy dinner at local inns by a fireplace, mountain views! Enjoy Vermont! Scenic roads, Prospect Mt. or Mt. Snow, VAST trails, hiking, Mt.Greylock, Mass MOCA, in nearby N.Adams, MA, (12 min)Berkshires w/in an hour. 20 mins to Bennington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺
Sep 13 – 20
$66 per night

Popular amenities for Windham County house rentals

House rentals with a pool

Guest favorite
Home in Wilmington
4 bedroom Ski House 15 min to Mount Snow
Nov 12 – 19
$186 per night
Guest favorite
Home in Wilmington
Adams Farm-"The Little Farmhouse"
Jul 14 – 21
$298 per night
Guest favorite
Home in Wilmington
The Vermont Barn (Mount Snow)
Apr 11 – 18
$277 per night
Guest favorite
Home in Peru
Beautiful Bromley/Manchester VT Retreat w/hot tub
Nov 12 – 19
$299 per night
Guest favorite
Home in Wilmington
Mountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow
Sep 4 – 11
$283 per night
Guest favorite
Home in Dover
Seasons-Ski on/off. Access to all amenities
Apr 3 – 10
$207 per night
Guest favorite
Home in Wardsboro
3 bedroom 10 minutes to mt snow 20 to Stratton
Mar 14 – 21
$209 per night
Guest favorite
Home in Wilmington
Silver Moose Lodge (Mt Snow)
Mar 31 – Apr 7
$349 per night
Superhost
Home in Wilmington
Stylish Chimney Hill Home - Close to Mt. Snow!
Sep 13 – 20
$228 per night
Guest favorite
Home in Wardsboro
Mt Snow/Stratton VT Getaway! w/Hot Tub + Game Room
Jul 16 – 23
$615 per night
Guest favorite
Home in Wardsboro
5BR Chalet, Hot Tub, Close to Mt Snow & Stratton
Jun 7 – 14
$320 per night
Guest favorite
Home in Londonderry
Dip, ride, ski … repeat. Magic, Okemo, Stratton!
Jan 14 – 21
$890 per night

Weekly house rentals

Guest favorite
Home in Winhall
Modern Cabin with Hot Tub & EV Charging Station
Aug 2 – 9
$357 per night
Guest favorite
Home in Winhall
Stunning mid-century house on 2.5 private acres
May 23 – 30
$269 per night
Superhost
Home in Putney
Spacious Loft with View
Jun 15 – 22
$146 per night
Guest favorite
Home in Putney
Lovely Brick Schoolhouse
Oct 8 – 15
$200 per night
Guest favorite
Home in Wilmington
Vermont Sugar House Retreat
Apr 18 – 25
$186 per night
Guest favorite
Home in West Brattleboro
Cozy Home for 2-5 People in Vermont
Oct 1 – 8
$158 per night
Superhost
Home in Brattleboro
Cozy Cabin Retreat on the River
Apr 2 – 9
$233 per night
Guest favorite
Home in Dover
Mt Snow retreat, ski & summer
Apr 23 – 30
$128 per night
Guest favorite
Home in Winhall
A+ Stratton shuttle, Hot Tub, Sauna, 2 masters
Apr 21 – 28
$546 per night
Guest favorite
Home in Putney
Preston’s Pond-Beautiful home on Tranquil Hilltop
Apr 12 – 19
$150 per night
Guest favorite
Home in Wilmington
Wilmington. Easy walk to center of town.
Mar 31 – Apr 7
$203 per night
Guest favorite
Home in Jamaica
Cozy Riverfront Home in beautiful Jamaica
Feb 3 – 10
$253 per night

Private house rentals

Guest favorite
Home in East Dover
Magical Retreat Cottage - Vermont cabin getaway
Jan 29 – Feb 5
$164 per night
Superhost
Home in South Londonderry
The Honey Pond Treehouse with hot tub & sauna
Jan 29 – Feb 5
$350 per night
Guest favorite
Home in Jamaica
The Post Haus: one-of-a-kind modern VT experience
Sep 5 – 12
$329 per night
Guest favorite
Home in West Brattleboro
Modern Spacious Home with Mountain Views
Feb 20 – 27
$179 per night
Guest favorite
Home in Brattleboro
Frosted Willows
Sep 14 – 21
$169 per night
Guest favorite
Home in Jamaica
2-Bedroom Home, 7 Minutes From Stratton Mountain
Sep 1 – 8
$137 per night
Guest favorite
Home in Newfane
Riverside Farmhouse
Feb 5 – 12
$169 per night
Guest favorite
Home in Wardsboro
Hot Tub & Game Room - Ski Mt. Snow/Stratton
Dec 17 – 24
$879 per night
Guest favorite
Home in Wilmington
Find your escape at The Coldbrook House, Mt Snow
Mar 17 – 24
$855 per night
Guest favorite
Home in Chesterfield
The River House
Mar 28 – Apr 4
$137 per night
Guest favorite
Home in West Brattleboro
Private Brookside Farmhouse
Dec 13 – 20
$167 per night
Guest favorite
Home in Wilmington
Private home, near Mt. Snow, lake, and downtown
Aug 26 – Sep 2
$182 per night

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