Top Guest Houses in Windham County in 2026

New England is known for their covered bridges. A beautiful example is the West Dummerston Bridge over the West River in southern Vermont.
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Top Cities in Windham County

Autumn colors along Connecticut River, Brattleboro, Vermont

HGY9XC View of the Ball Mountain Reservoir from the top of the Ball Mountain Dam on the West River in Jamaica Vermont USA

Our top choices for Windham County guest houses

The Inn At Quail Run

Wilmington

Tami

HK$1,936 total

includes taxes & fees

3 Mar - 4 Mar

Cozy, charming cottage 7 mins from Mount Snow and Lake Whitingham

Wilmington

Christine B.

New! remodeled Barn. min from Lake, Ski, Hot tub

Wilmington

"This barn was very clean and cozy. We loved all of the original wood and morning sunlight. It is attached to another house and shares a driveway. The hot tub was easy to use, although the directions were outdated. The property manager was very responsive and answered questions quickly. At night, the stars were extremely visible. Wilmington was a great small town with good food and local shopping. Would stay again and recommend to others."

Colleen G.

Pristine Magical Retreat Cottage - 15 min to Mt Snow skiing

East Dover

Joseph G.

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Top Windham County Hotel Reviews

Farm Road Estate

10/10 Excellent

"Very clean room, all the necessary amenities in the room, comfortable bed, etc. Staff very friendly and helpful!"

The Covered Bridge Inn

10/10 Excellent

"My room was clean and spacious. Bed was very comfortable. Mini fridge and microwave a big plus! I normally stay at a different hotel when I come up to visit my family but I decided to try this hotel. I wasn't sure how it would be but I was pleasantly surprised! Clean, quiet and the gentleman who always seems to be at the front desk.. I'm sorry I can't remember his name is awesome! I was there for 3 weeks and I loved it! 10/10"

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"We loved our stay at the Black Bear! The check-in went smoothly with desk staff, Noah. She was very helpful and went over everything about our stay. The room was very clean. The hot tub was very nice and clean and a welcome after a day on the slopes. The shuttle to the mountain was great and ran frequently. The breakfast was always hot and had many options. We would definitely stay there again!"