Chesterfield
Travel Guide
Visit Chesterfield
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is CA $133 per night from Feb 22 to Feb 23
CA $133
CA $155 total
Feb 22 - Feb 23
includes taxes & fees
Book a stay at this 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! (2,238 reviews)
Clean, safe, quiet, and comfortable. Fantastic full breakfast as always.
Reviewed on Feb 6, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is CA $135 per night from Feb 11 to Feb 12
CA $135
CA $181 total
Feb 11 - Feb 12
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (830 reviews)
The doors wouldn’t stay locked
Reviewed on Feb 6, 2026
Comfort Inn & Suites
400 Russell St Hadley MA
The price is CA $153 per night from Mar 1 to Mar 2
CA $153
CA $170 total
Mar 1 - Mar 2
includes taxes & fees
Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,003 reviews)
Clean room, friendly staff,
Reviewed on Feb 1, 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.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough MA
Stay at this vacation home in Lanesborough. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
10/10 Exceptional! (10 reviews)
Perfect spot to get in a few days of skiing at Jiminy. Well stocked with the basics and hot tub was great. Very responsive host.
Reviewed on Jan 18, 2026
Peace and quiet on the lake
Becket MA
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.4/10 Exceptional! (233 reviews)
Justin was very responsive and helpful. They left a gift basket with lots of yummy treats for us. The house is very cozy and just about anything you may need is there. It was extremely cold the days we were there and the ground was snow covered so we didn't get a chance to spend time outside. You ...
Reviewed on Jan 29, 2026
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! (47 reviews)
Beautifully appointed and comfortable.
Reviewed on Jan 4, 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
Chesterfield Gorge
Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forest 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.
