Chesterfield, MA

Travel Guide

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 Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total includes 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 ...
8.8/10 Excellent! (561 reviews)
Rest, relax, and repeat
"Great value for families! The welcoming staff, location (Lenox/Pittsfield border), spacious suite, and ample amenities made for a fantastic vacation. No free breakfast but there are several dining options and markets nearby. Gorgeous view of the sunset from the upper floors. There was a note of upcoming ..."

Reviewed on Aug 14, 2025

Berkshire Mountain Lodge
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $99 total per night from Aug 24 to Aug 25
$99 total
Aug 24 - Aug 25
Total includes 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! (1,001 reviews)
Enjoyable one night stay at the Quality Inn!
"I recently stayed 1 night at the Quality Inn while in the area for Six Flags. This is my go to hotel when visiting the park as it is a great value and about 15 minutes away. I checked in later, around 9pm, and long time employee Rick was at the desk. He is never shy about his dislike for computers ..."

Reviewed on Aug 12, 2025

Quality Inn West Springfield
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
$119 nightly
The price is $132 total per night from Aug 17 to Aug 18
$132 total
Aug 17 - Aug 18
Total includes taxes and fees
Stay at this 3-star 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! (2,217 reviews)
"Lovely property. The front desk clerk was angry and bitter and the breakfast was underwhelming but otherwise, ok."

Reviewed on Aug 13, 2025

D. Hotel Suites & Spa
See all 466 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.
Easthampton Vacation Rental - Walk to Breweries!

Easthampton Vacation Rental - Walk to Breweries!

Easthampton
Stay at this apartment in Easthampton. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Mount Tom State Reservation and Mount Tom are located ...
9.6/10 Exceptional! (14 reviews)
Great Location
"Nice little property in a great location. Easy access to Northampton and trails."

Reviewed on Aug 2, 2025

Easthampton Vacation Rental - Walk to Breweries!
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! (187 reviews)
My stay
"Everything was great: kitchen, WiFI, etc."

Reviewed on Aug 6, 2025

The Clearing - Quiet - Close To Nature
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! (216 reviews)
Lake House Getaway with Access to Berkshire Highlights
"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any ..."

Reviewed on Jul 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