Winchester Travel Guide
Tourist Guide





Visit Winchester

The Colonial Hotel
The room was clean though a bit depressing. The curtains and carpet could use a refresher as could the paint in the hallways and in the room. The evening front desk clerk seemed a little scattered and he couldn't be bothered with client service. The morning staff was courteous and helpful.
Reviewed on 9 Feb 2026

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

Hampton Inn Brattleboro
The room was very clean, and the showers hot water was amazing! The staff was friendly and would let us know when breakfast was available so we wouldn’t miss it ! Robert and Destiny always had a smile on their face and greeted us when we arrived and when we left the hotel. I would definitely stay ...
Reviewed on 9 Feb 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

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 15 Jan 2026

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
It was a lovely stay! Lake is beautiful and the house is cozy.
Reviewed on 16 Oct 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.
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.
Loring Field
Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.




