Winchester
Travel Guide





Visit Winchester

The Colonial Hotel
Friendly staff, clean room, gym and poll area.
Reviewed on Feb 4, 2026

Comfort Inn & Suites Brattleboro I-91
Nice location… clean room! Breakfast was not appetizing…
Reviewed on Jan 29, 2026

Hampton Inn Brattleboro
Recently renovated room
Reviewed on Jan 27, 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 Nov 17, 2025

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Everything was very nice and welcoming in the cottage- exactly what we were looking for.
Reviewed on Jan 15, 2026

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Julie was wonderful, quick to respond and very helpful. The house itself was perfect for a long ski weekend with my family. Plenty of space for the kids to have fun in the basement while the adults kicked back upstairs. The view, the decor, everything was marvelous. Also, one of the best stocked ...
Reviewed on Jan 4, 2026
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.
Barden State Wildlife Management Area
Explore the great outdoors at Barden State Wildlife Management Area, a lovely green space in Richmond.
Richmond Town Hall
After visiting Richmond Town Hall, make a plan to see the other sights and activities in Richmond.
Bennett Gorge
You can take time to visit Bennett Gorge during your travels to Richmond.
Winchester Speedpark
You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside.
Cass Pond
Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.
