4/5 - Good
Verified traveler
We found a great diner, the food was delicious and the staff was wonderful. The only drawback was it being so far away from any major stores.
Visit Winchester
The Colonial Hotel
625 Betty Spring Road Gardner MA
$160 nightly
The price is $179 total per night from Dec 8 to Dec 9
$179 total
Dec 8 - Dec 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Gardner. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,000 reviews)
Clean room pool was cold.
Reviewed on Nov 29, 2025
Hampton Inn & Suites Greenfield
184 Shelburne Rd Greenfield MA
$183 nightly
The price is $205 total per night from Dec 14 to Dec 15
$205 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this business-friendly hotel in Greenfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (875 reviews)
Staff was friendly, room was very nice and really appreciate the breakfast.
Reviewed on Nov 25, 2025
The Covered Bridge Inn
1043 Putney Road Brattleboro VT
$79 nightly
The price is $87 total per night from Dec 8 to Dec 9
$87 total
Dec 8 - Dec 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,001 reviews)
Room very nice, comfortable clean
Reviewed on Nov 29, 2025
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.
FaLL Western Mass Getaway-Airhockey-Firepit
Colrain MA
Book a stay at this family-friendly vacation home in Colrain. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Arthur A. ...
9.8/10 Exceptional! (37 reviews)
We love the layout and the beautiful chalkboard of activities and places to see. Great decor and furnishings. We had a lot of fun on the air hockey table and love the cozy fun kitchen area.
Reviewed on Oct 28, 2025
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Fitzwilliam NH
Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Sportsman Pond and Laurel Lake are located nearby.
10/10 Exceptional! (10 reviews)
It was a lovely stay! Lake is beautiful and the house is cozy.
Reviewed on Oct 16, 2025
Lovely 2nd Floor Apartment
Greenfield MA
Book a stay at this family-friendly vacation home in Greenfield. Enjoy a garden, an in-room coffeemaker, and housekeeping. Popular attractions Poet's Seat Tower ...
10/10 Exceptional! (44 reviews)
Great every time! Thanks David
Reviewed on Dec 2, 2025
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.
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.
Bennett Gorge
You can take time to visit Bennett Gorge during your travels to 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.
Richmond Wildlife Manangement Area
Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.
Conant Public Library
After visiting Conant Public Library, make a plan to see the other sights and activities in Winchester. While you're in the area, stroll along the lakeside.
Reviews of Winchester
4
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- Green Mountain National Forest
- Keene State College
- Connecticut River
- Northfield Mount Hermon School
- Cushing Academy
- Landmark College
- The Stone Church
- Deerfield Academy
- Historic Main Street
- Spofford Lake
- Historic Deerfield Village
- Colonial Theatre
- Monadnock State Park
- Eaglebrook School
- Bridge of Flowers
- Pack Monadnock Mountain
- Molly Stark State Park
- Mount Wachusett Community College
- Vermont Marketplace
