Winchester
Travel 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! (1,003 reviews)
Staff were friendly and efficient. Room was clean and fully stocked
Reviewed on 28 Feb 2026
Colonial Motel And Spa
889 Putney Rd Brattleboro VT
The price is €88 per night from 2 Mar to 3 Mar
€88
2 Mar - 3 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 (1,003 reviews)
The room was old and run down. The building we were in was very sketchy. People next to us were up partying/noisy until all hours of the night, and there was a dog barking until 2:00am right below us. I had a horrible nights sleep. The pillows were flat as pancakes, the towels were the roughest/scratchiest ...
Reviewed on 24 Feb 2026
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
The price is €99 per night from 9 Mar to 10 Mar
€99
9 Mar - 10 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
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.
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.
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.
Bennett Gorge
You can take time to visit Bennett Gorge during your travels to Richmond.
