Chesterfield, MA

Travel Guide

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Nov 6 to Nov 7
$126 total
Nov 6 - Nov 7
Total with taxes and fees
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! (745 reviews)
Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you

Reviewed on Nov 2, 2025

Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
$86 nightly
The price is $99 total per night from Dec 2 to Dec 3
$99 total
Dec 2 - Dec 3
Total with taxes and 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! (1,041 reviews)
Everything was okay I think just slightly overpriced

Reviewed on Nov 2, 2025

Quality Inn West Springfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
$103 nightly
The price is $115 total per night from Nov 9 to Nov 10
$115 total
Nov 9 - Nov 10
Total with taxes and 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! (938 reviews)
Spotless and friendly staff

Reviewed on Nov 2, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 483 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.
The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Cummington
Stay at this cottage in Cummington. Enjoy free WiFi, private pools, and a garden. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (199 reviews)
Everything was amazing!

Reviewed on Oct 20, 2025

The Clearing - Quiet - Close To Nature
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
Book a stay at this family-friendly vacation home in Lenox. Enjoy private pools, laundry facilities, and in-room jetted tubs. Popular attractions Tanglewood ...
9/10 Wonderful! (31 reviews)
Great stay

Reviewed on Oct 8, 2025

Amore Estate - beautiful room with many places to explore and relax in.
Peace and quiet on the lake

Peace and quiet on the lake

Becket
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 ...
9.6/10 Exceptional! (227 reviews)
Great peaceful weekend in this beautiful home.

Reviewed on Oct 31, 2025

Peace and quiet on the lake
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

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.

Krug Sugarbush

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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