Chesterfield, MA
Travel Guide
Visit Chesterfield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
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 ...
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.
Reviewed on Nov 4, 2025
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
The price is ₩123,771 per night from Dec 7 to Dec 8
₩123,771
₩141,657 total
Dec 7 - Dec 8
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! (1,004 reviews)
The owner makes me feel like I am a personal friend of his and the best part of his day is when I walk in the door.
Reviewed on Nov 7, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
The price is ₩143,206 per night from Nov 21 to Nov 22
₩143,206
₩159,962 total
Nov 21 - Nov 22
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (946 reviews)
Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned.
Reviewed on Nov 8, 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.
Westfield Vacation Rental w/ Porch, Pets Welcome!
Westfield
Stay at this 3-star cottage in Westfield. Enjoy free parking and air conditioning. Popular attractions Stanley Park and Woodward Center are located nearby.
Easthampton Apartment Near Breweries & Rail Trail!
Easthampton
Stay at this 3-star business-friendly apartment in Easthampton. Enjoy free parking and air conditioning. Popular attractions Mount Tom State Reservation and ...
Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!
Charlemont
Stay at this 3-star cottage in Charlemont. Enjoy air conditioning. Popular attractions Hawley Bog Preserve and Berkshire East Ski Resort are located nearby.
10/10 Exceptional! (1 review)
Loved this old home! Record player and records were fun to listen to. Pickle ball across the street was excellent! Well stocked kitchen great for cooking in. I had a tough time with water pressure and temperature but it could have been user error. Beds were comfortable except for the twin, which ...
Reviewed on Oct 14, 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 forest while you're in the area.
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.
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.
