Chesterfield

Name: Holiday Inn & Suites Pittsfield-Berkshires by IHG
Price range: €93
Rating: 8

Travel Guide

Visit Chesterfield

Things to do

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

€117

29 Jan - 30 Jan

includes taxes & fees

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 their reviews. Popular ...

9.2/10 Wonderful! (2,243 reviews)

Great, great place!

Reviewed on 22 Jan 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

€112

1 Feb - 2 Feb

includes taxes & fees

Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...

9/10 Wonderful! (816 reviews)

Clean, great location near Bosquet Mountain and grocery store, spacious condo, easy.

Reviewed on 19 Jan 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

€93

30 Jan - 31 Jan

includes taxes & fees

Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

8/10 Very Good! (1,000 reviews)

generally good

Reviewed on 19 Jan 2026

See all 503 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!

Lanesborough MA

Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, 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 18 Jan 2026

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket MA

Stay at this cabin in Becket. Enjoy a garden, laundry facilities and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...

9.4/10 Exceptional! (203 reviews)

Nice cozy cabin. Everything we needed was there.

Reviewed on 19 Jan 2026

Lovely 2nd Floor Apartment

Greenfield MA

Stay at this family-friendly holiday home in Greenfield. Enjoy a garden, an in-room coffee maker and housekeeping. Popular attractions Poet's Seat Tower and ...

10/10 Exceptional! (47 reviews)

Beautifully appointed and comfortable.

Reviewed on 4 Jan 2026

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 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.