Chesterfield, MA
Travel Guide
Visit Chesterfield
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
The price is ￥16,910 per night from Jan 15 to Jan 16
￥16,910
￥19,643 total
Jan 15 - Jan 16
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! (2,266 reviews)
The front staff upon arrival was incredibly kind and accommodating. We loved the pool and hot tub and the quiet, clean room. It was large and had everything we expected. The breakfast was also great- lots of options for everyone in our family! Thank you.
Reviewed on Jan 11, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is ￥15,582 per night from Feb 1 to Feb 2
￥15,582
￥20,932 total
Feb 1 - Feb 2
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! (810 reviews)
Very comfortable and very close to ski slope and restaurants
Reviewed on Jan 10, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
The price is ￥15,473 per night from Jan 23 to Jan 24
￥15,473
￥17,284 total
Jan 23 - Jan 24
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,004 reviews)
Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...
Reviewed on Jan 7, 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! (6 reviews)
Beautiful lake house, isolated enough that you're not in the city, but close access to amenities and good food. The hot tub was an absolutely amazing experience, and Adam was thoughtful with providing instructions on how to use the firepit and outdoor heating as well. Would love to stay here ...
Reviewed on Dec 4, 2025
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! (230 reviews)
The veiws and how peacefull it was
Reviewed on Nov 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! (46 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
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 Gorge Reservation
You can take time to visit Chesterfield Gorge Reservation during your travels to Chesterfield. Amble around the area's parks or visit its shops.
