Winchester
Travel Guide




Visit Winchester

The Colonial Hotel
Everything about the hotel is great.
Reviewed on 19 Apr 2026

Colonial Motel And Spa
Awesome and clean and quiet love the staff
Reviewed on 14 Apr 2026

Hampton Inn Brattleboro
The construction right below our room until after 9:30pm was aweful. I'm surprised we weren't at least placed in a room further from the construction. Hot tub was brown, not at all like the photos. The room was clean so that met expectations.
Reviewed on 17 Apr 2026

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Fireplace heated the area very nice in the middle of a cold snowy winter.
Reviewed on 17 Apr 2026

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Beautiful house, immaculate and cool space! Perfect overnight after catching a show at Shea Theater.
Reviewed on 12 Apr 2026

Lovely 2nd Floor Apartment
Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!
Reviewed on 19 Apr 2026
Popular places to visit
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.
Barden State Wildlife Management Area
Explore the great outdoors at Barden State Wildlife Management Area, a lovely green space in Richmond.
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.
Richmond Wildlife Manangement Area
Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.
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.
