Chesterfield, MA

Travel Guide

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
The price is SAR 437 per night from Jan 27 to Jan 28
SAR 437
SAR 507 total
27 Jan - 28 Jan
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 11 January 2026

D. Hotel Suites & Spa
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is SAR 370 per night from Feb 2 to Feb 3
SAR 370
SAR 497 total
2 Feb - 3 Feb
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 10 January 2026

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
The price is SAR 368 per night from Jan 30 to Jan 31
SAR 368
SAR 411 total
30 Jan - 31 Jan
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 7 January 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 490 properties in Chesterfield
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!

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 4 December 2025

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Peace and quiet on the lake

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 16 November 2025

Peace and quiet on the lake
Lovely 2nd Floor Apartment

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 2 December 2025

Lovely 2nd Floor Apartment
See all properties in Chesterfield
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 Gorge

Chesterfield Town Hall

After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.

Chesterfield Town Hall

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.

Chesterfield Gorge Reservation