Chesterfield, MA

Travel Guide

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is $173 total per night from Jun 21 to Jun 22
$173 total
per night
Jun 21 - Jun 22
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! (991 reviews)
"Very clean room and kitchen. Sofa needs to be replaced. Staff was excellent! Great location!"

Reviewed on Jun 19, 2026

Berkshire Mountain Lodge
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
The price is $161 total per night from Jul 2 to Jul 3
$161 total
per night
Jul 2 - Jul 3
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and 5 coffee shops/cafes. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,005 reviews)
"Nice hotel, conveniently located, central UMASS campus. Nice breakfast in the lobby. Loved the automatic espresso machine. Genius! Also very much appreciated the extra steps to have gluten free items and keep them separate to avoid cross-contamination. It makes a difference for some of us. Thank ..."

Reviewed on Jun 19, 2026

Hotel UMass
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
The price is $105 total per night from Jul 14 to Jul 15
$105 total
per night
Jul 14 - Jul 15
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 ...
Quality Inn West Springfield
See all 506 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 1-bedroom house in overlooking the river close to downtown Northampton

Cozy 1-bedroom house in overlooking the river close to downtown Northampton

Northampton MA
Stay at this vacation home in Northampton. Enjoy free WiFi, laundry facilities, and air conditioning. Popular attractions Connecticut River Greenway State Park ...
10/10 Exceptional! (7 reviews)
"Very cute place!! Convenient"

Reviewed on Jun 14, 2026

Cozy 1-bedroom house in overlooking the river close to downtown Northampton
Family Friendly Modern 3-bedroom Cottage w/ central AC & high end appliances

Family Friendly Modern 3-bedroom Cottage w/ central AC & high end appliances

Chester MA
Stay at this cottage in Huntington. Enjoy a garden, laundry facilities, and patios. Popular attractions Glendale Falls and Fox Den Wildlife Management Area are ...
Family Friendly Modern 3-bedroom Cottage w/ central AC & high end appliances
Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet

Becket MA
Book a stay at this family-friendly chalet in Becket. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Pyramid Lake and Jacob's ...
9.8/10 Exceptional! (27 reviews)
"Good location in the berkshires. Property is private and pretty with lots of amenities."

Reviewed on Jun 15, 2026

Little Longbow Lakefront Chalet
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

Cities near Chesterfield

Huntington

Huntington

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