House vacation rentals in Windham County
Find and book unique houses on Airbnb
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"
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Home in Peru
4.91 out of 5 average rating, 141 reviewsBeautiful Bromley/Manchester VT Retreat w/hot tub
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Home in Dover
5.0 out of 5 average rating, 22 reviewsCozy VT 3bd condo:Come golf,mtn bike& hike@Mt snow
Home in Wardsboro
5.0 out of 5 average rating, 11 reviewsSheldon Hill Chalet | 4BR Home by Mt Snow/Stratton
Home in Wilmington
4.87 out of 5 average rating, 23 reviewsMountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow
Home in Wardsboro
5.0 out of 5 average rating, 31 reviewsSummer getaway! Hot Tub, Fire Pit, Game Room, AC!
Weekly house rentals
Home in Wilmington
4.94 out of 5 average rating, 242 reviewsWilmington. Easy walk to center of town.
Home in Brattleboro
4.94 out of 5 average rating, 102 reviewsSpacious Brattleboro home on river, walk to town
Home in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow retreat, ski & summer
Home in Brattleboro
4.95 out of 5 average rating, 110 reviewsFrosted Willows
Home in Putney
4.85 out of 5 average rating, 233 reviewsPreston’s Pond-Beautiful home on Tranquil Hilltop
Home in Jamaica
4.96 out of 5 average rating, 158 reviewsCozy Riverfront Home in beautiful Jamaica
Home in Weston
4.95 out of 5 average rating, 231 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Home in Dover
4.98 out of 5 average rating, 125 reviewsOutdoor Paradise - Private Jacuzzi & Sauna
Private house rentals
Home in Jamaica
5.0 out of 5 average rating, 26 reviews2-Bedroom Home, 7 Minutes From Stratton Mountain
Home in Guilford
4.91 out of 5 average rating, 32 reviewsWoodland Retreat in Maple Sugarbush, EV
Home in Chesterfield
4.92 out of 5 average rating, 87 reviewsGoverner's Brook Camp - 2 Bedroom
Home in Jamaica
5.0 out of 5 average rating, 3 reviewsSnowed Inn at Stratton (Private home in Winhall)
Home in Newfane
4.96 out of 5 average rating, 76 reviewsClark Farm-2 Master-Suites, Great kitchen, views!
Home in Grafton
4.92 out of 5 average rating, 59 reviewsGrafton Artist Retreat With Pond Near Skiing
Home in Whitingham
5.0 out of 5 average rating, 64 reviewsLakefront with Spectacular Sunset/Mountain Views
Home in Wardsboro
4.98 out of 5 average rating, 80 reviewsHot Tub & Game Room - Ski Mt. Snow/Stratton
Destinations to explore
- Lighthouse rentals United States
- Townhouse rentals United States
- Earth house rentals United States
- House rentals United States
- Guesthouse rentals United States
- Beach house rentals Boston
- House rentals Boston
- Guesthouse rentals Boston
- Townhouse rentals Boston
- Townhouse rentals Vermont
- Treehouse rentals Vermont
- House rentals Vermont
- Lake house rentals Vermont
- Guesthouse rentals Vermont
- Tiny house rentals Vermont
- Tiny house rentals New York
- Townhouse rentals New York
- Treehouse rentals New York
- Guesthouse rentals New York
- House rentals New York
- Lake house rentals New Hampshire
- House rentals New Hampshire
- Guesthouse rentals New Hampshire
- Treehouse rentals New Hampshire
- Townhouse rentals New Hampshire
- Beach house rentals New Hampshire
- Tiny house rentals New Hampshire
- Rentals with pools Windham County
- Monthly Rentals Windham County
- Cabin rentals Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- Rentals with a kayak Windham County
- Rentals with breakfast Windham County
- Beachfront rentals Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with a fireplace Windham County
- Chalet rentals Windham County
- Fitness-friendly rentals Windham County
- Rentals with a hot tub Windham County
- Bed and breakfasts Windham County
- Guesthouse rentals Windham County
- Tiny house rentals Windham County
- Farmstay rentals Windham County
- Private suite rentals Windham County
- Pet-friendly rentals Windham County
- Rentals with an accessible height toilet Windham County
- Townhouse rentals Windham County
- Rentals with a sauna Windham County
- Rentals with beach access Windham County
- Apartment rentals Windham County
- Rentals with outdoor seating Windham County
- Family-friendly rentals Windham County
- Rentals with a washer and dryer Windham County
- Rentals with a patio Windham County
- Rentals with an EV charger Windham County
- Rentals with lake access Windham County
- Rentals with a firepit Windham County
- Condo rentals Windham County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom