Chesterfield, MA

Travel Guide

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
$134 nightly
The price is $149 total per night from Jan 1 to Jan 2
$149 total
Jan 1 - Jan 2, 2026
Total with taxes and 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! (2,259 reviews)
Everything was perfect.

Reviewed on Dec 17, 2025

D. Hotel Suites & Spa
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
$93 nightly
The price is $104 total per night from Dec 23 to Dec 24
$104 total
Dec 23 - Dec 24
Total with taxes and 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! (988 reviews)
Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful .

Reviewed on Dec 15, 2025

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

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night from Jan 19 to Jan 20
$120 total
Jan 19 - Jan 20, 2026
Total with taxes and 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! (792 reviews)
Spacious room and loved pool and hot tub!

Reviewed on Dec 19, 2025

Berkshire Mountain Lodge
See all 487 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.
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 Nov 16, 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 Dec 2, 2025

Lovely 2nd Floor Apartment
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 Dec 4, 2025

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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 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.

Chesterfield Public Library

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