Visit Winchester

The Colonial Hotel
Well-kept hotel with a great restaurant.
Reviewed on 13 Jan 2026

Comfort Inn & Suites Brattleboro I-91
Great staff
Reviewed on 5 Jan 2026

The Covered Bridge Inn
staff was wonderful. the room was clean. hotels dot com said breakfast is included but there was no breakfast included at this hotel. this was important to me as my car broke down and I had no transportation so I was a little upset about that. there was a food market in walking distance and a microwave ...
Reviewed on 10 Jan 2026

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
The home was as pictured. Great space to host larger groups of people
Reviewed on 17 Nov 2025

Lovely 2nd Floor Apartment
Great every time! Thanks David
Reviewed on 2 Dec 2025

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
A beautiful, cozy home. My dog loved it too!
Reviewed on 2 Dec 2025
Popular places to visit
New England Sweetwater Farm & Distillery
You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.
Bennett Gorge
You can take time to visit Bennett Gorge during your travels to Richmond.
Cass Pond
Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.
Richmond Town Hall
After visiting Richmond Town Hall, make a plan to see the other sights and activities in Richmond.
Barden State Wildlife Management Area
Explore the great outdoors at Barden State Wildlife Management Area, a lovely green space in Richmond.
Richmond Wildlife Manangement Area
Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.

