Chesterfield
Travel Guide
Visit Chesterfield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is €109 per night from 2 Nov to 3 Nov
€109
2 Nov - 3 Nov
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (705 reviews)
"Nice property, a little worn but clean. Plenty of space in our room. One negative, our room (124) seemed to be under a waterfall each someone upstairs flushed."
Reviewed on 15 Oct 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
The price is €89 per night from 16 Nov to 17 Nov
€89
16 Nov - 17 Nov
includes taxes & fees
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,019 reviews)
Great hotel for a cheap night passing through town
"Over all great stay. Looking for a decent place to overnight traveling back home from a vacation. Check in process was easy and greeting immediately with a friendly staff member who appeared to be training but still very efficient at their job. We were giving directions to the elevators and went ..."
Reviewed on 13 Oct 2025
D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is €110 per night from 27 Oct to 28 Oct
€110
27 Oct - 28 Oct
includes taxes & fees
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,252 reviews)
"We’ve stayed here every fall for the past 3 years, and will continue doing so. Suite is spacious, breakfast is good, employees are kind and respectful."
Reviewed on 17 Oct 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.
The Clearing - Quiet - Close To Nature
Cummington
Stay at this cottage in Cummington. Enjoy free WiFi, private pools, and a garden. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (195 reviews)
"We had an incredible time. The location was amazing, quiet, and peaceful. We nixed all plans of exploration and restaurants and just stayed and relaxed for days. We couldn’t have asked for more. What a gem. We will absolutely be back!"
Reviewed on 16 Oct 2025
Amore Estate - beautiful room with many places to explore and relax in.
Lenox
Book a stay at this family-friendly vacation home in Lenox. Enjoy private pools, laundry facilities, and in-room jetted tubs. Popular attractions Tanglewood ...
9/10 Wonderful! (31 reviews)
"Great stay"
Reviewed on 8 Oct 2025
Bear Creek Cabin
Charlemont
Stay at this cabin in Charlemont. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Rowe Town Forest and Hail to the Sunrise Statue are located ...
9.8/10 Exceptional! (41 reviews)
"Clean with unique cabin feel."
Reviewed on 12 Oct 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
Chesterfield Gorge
Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.
Krug Sugarbush
You can take time to visit Krug Sugarbush during your travels to Chesterfield. Amble around the area's parks or visit its shops.
Chesterfield Public Library
Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
