Guesthouse vacation rentals in Windham County
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Windham County
Guests agree: these guesthouse rentals 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 guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Jamaica
4.95 out of 5 average rating, 155 reviewsThe Chick Inn
Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
Guesthouse in Putney
4.95 out of 5 average rating, 334 reviewsA Vermont Carriage House
Guesthouse in Brattleboro
4.99 out of 5 average rating, 217 reviewsLight Filled Loft in the Vermont Countryside
Guest house rentals with a patio
Guesthouse in Wilmington
5 out of 5 average rating, 4 reviewsRenovated guest house. Min from Lake and Skiing.
Private room in Newfane
4.82 out of 5 average rating, 11 reviewsYogi & artist retreat center
Guesthouse in Chester
5 out of 5 average rating, 13 reviewsNew in town Chester Retreat, 14 Miles to Okemo!
Private room in Newfane
5 out of 5 average rating, 3 reviewsQueen bed + private bath, breakfast included
Guest house rentals with a washer and dryer
Guesthouse in Wilmington
4.9 out of 5 average rating, 68 reviewsNew! remodeled Barn. min from Lake, Ski, Hot tub
Guesthouse in Town of Rockingham
4.85 out of 5 average rating, 27 reviewsPeaceful Historic Cottage
Guesthouse in Wilmington
5 out of 5 average rating, 4 reviewsRenovated guest house. Min from Lake and Skiing.
Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviewsThe Inn at Quail Run- Guest House
Guesthouse in Wilmington
5 out of 5 average rating, 29 reviewsCozy, charming cottage 7 mins from Mount Snow
Guesthouse in Jamaica
4.85 out of 5 average rating, 60 reviews5 min to Stratton, pet friendly, fire pit
Guesthouse in Marlboro
4.97 out of 5 average rating, 157 reviewsRefined, serene and like no other, Marlboro, VT.
Destinations to explore
- House rentals United States
- Guesthouse rentals United States
- House rentals Boston
- Guesthouse rentals Boston
- Guesthouse rentals Vermont
- House rentals Vermont
- House rentals New York
- Guesthouse rentals New York
- Rentals with a fireplace Windham County
- Rentals with an accessible height toilet Windham County
- Farmstay rentals Windham County
- Rentals with outdoor seating Windham County
- Fitness-friendly rentals Windham County
- Kid-friendly rentals Windham County
- Waterfront rentals Windham County
- Pet-friendly rentals Windham County
- Chalet rentals Windham County
- Townhouse rentals Windham County
- Rentals with breakfast Windham County
- Tiny house rentals Windham County
- Apartment rentals Windham County
- Rentals with pools Windham County
- Private suite rentals Windham County
- Rentals with a patio Windham County
- Rentals with beach access Windham County
- Bed and breakfasts Windham County
- Condo rentals Windham County
- Cabin rentals Windham County
- Monthly Rentals Windham County
- Rentals with a hot tub Windham County
- Rentals with a washer and dryer Windham County
- Rentals with lake access Windham County
- Family-friendly rentals Windham County
- Rentals with a fire pit Windham County
- House rentals Windham County
- Rentals with a sauna Windham County
- Beachfront rentals Windham County
- Ski-in/ski-out rentals Windham County
- Rentals with a kayak 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