Winchester Travel Guide
Tourist Guide
Visit Winchester
The Colonial Hotel
625 Betty Spring Road Gardner MA
Stay at this business-friendly hotel in Gardner. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful staff ...
8.8/10 Excellent! (1,008 reviews)
This property needs a serious update. The property looks tired. Attempted to use the fitness room and it was dirty and much of the equipment was unusable. The pool and jacuzzi were closed and looked disgusting. The common areas and room felt unclean
Reviewed on 2 Mar 2026
Colonial Motel And Spa
889 Putney Rd Brattleboro VT
The price is AU$149 per night from 9 Mar to 10 Mar
AU$149
9 Mar - 10 Mar
includes taxes & fees
Stay at this spa motel in Brattleboro. Enjoy free Wi-Fi, free parking and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in their reviews. ...
6.8/10 (1,005 reviews)
There are two sections to the property. We asked to switch rooms because it smelled moldy on the one side. The other was in much better conditions, no smell, rooms very large, and clean. The pool is run by another company and they are strict about pool hours.
Reviewed on 2 Mar 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
The price is AU$166 per night from 15 Mar to 16 Mar
AU$166
15 Mar - 16 Mar
includes taxes & fees
Stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (948 reviews)
Staff and clean room
Reviewed on 22 Feb 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Wilmington VT
Stay at this cottage in Wilmington. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions The Art of Humor Gallery and Lake Raponda ...
8.6/10 Excellent! (66 reviews)
Cozy and peaceful, just with they had turned the heat up before u got there. It was like 45-50 when I arrived and had to figure out the heating and wait for it to warm up for the first few hours.
Reviewed on 19 Feb 2026
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Townshend VT
Stay at this family-friendly holiday home in Townshend. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Townshend State Park and Townshend ...
10/10 Exceptional! (63 reviews)
Wonderful property. Perfect for our family trip. Plenty of room , the basement being the most used by the kids. Clean, neat with all the essentials. Large kitchen well stocked. Sledding on the property itself was priceless. Would definitely recommend and rent again. Hosts and property manager available ...
Reviewed on 5 Feb 2026
Lovely 2nd Floor Apartment
Greenfield MA
Stay at this family-friendly holiday home in Greenfield. Enjoy a garden, an in-room coffee maker and housekeeping. Popular attractions Poet's Seat Tower and ...
10/10 Exceptional! (49 reviews)
Very clean, cozy and lots of nice plants!
Reviewed on 26 Feb 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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.
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.
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.
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.
