Chesterfield, MA

Travel Guide

Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St West Springfield MA
$91 nightly
The price is $104 total per night from Aug 7 to Aug 8
$104 total
Aug 7 - Aug 8
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 ...
Quality Inn West Springfield
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night from Aug 16 to Aug 17
$173 total
Aug 16 - Aug 17
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! (1,008 reviews)
"The staff were very friendly and helpful. It’s a rustic style hotel room but having the full kitchen was amazing! Great location and cozy room."

Reviewed on Jul 17, 2026

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
$142 nightly
The price is $158 total per night from Jul 26 to Jul 27
$158 total
Jul 26 - Jul 27
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! (2,147 reviews)
"Overall the hotel is very good. Very clean really nice room. Restaurant was very good."

Reviewed on Jul 16, 2026

D. Hotel Suites & Spa
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.
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA
Stay at this cottage in Otis. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Larkum Pond and Otis Reservoir are located nearby.
8.6/10 Excellent! (9 reviews)
"Location was wonderful, panoramic lake view.Glassed in porch was the primo spot to just relax and chill. Main bedroom and living room were good size. Kitchen was well appointed except for one staple item, no microwave! Second bedroom and bathroom are very small. You’ll want to bring your own linens, ..."

Reviewed on Oct 14, 2025

Private Island - Largest Fresh Water Reservoir in Mass
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! (59 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"

Reviewed on Jul 8, 2026

Lovely 2nd Floor Apartment
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Sandisfield MA
Stay at this cabin in Sandisfield. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Lake Garfield and Otis Ridge are located ...
9.6/10 Exceptional! (54 reviews)
"We had a wonderful stay! The tennis court is a nice feature and the screened in porch was perfect for enjoying the passing summer storms while staying nice and dry."

Reviewed on Jul 2, 2026

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.

Stay near popular Chesterfield attractions

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.
See properties

Cities near Chesterfield

A rocky stream with cascading water surrounded by trees.

Huntington

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