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 Sep 21 to Sep 22
$126 total
Sep 21 - Sep 22
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 ...
8.8/10 Excellent! (640 reviews)
"Clean, bright, great value, love the hot tub and pool!"

Reviewed on Sep 15, 2025

Berkshire Mountain Lodge
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 out of 5
1254 Riverdale Street, West Springfield, MA
$89 nightly
The price is $102 total per night from Oct 1 to Oct 2
$102 total
Oct 1 - Oct 2
Total with taxes and fees
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,008 reviews)
"Excellent overall!"

Reviewed on Sep 13, 2025

Red Roof Inn PLUS+ West Springfield
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
$158 nightly
The price is $177 total per night from Sep 28 to Sep 29
$177 total
Sep 28 - Sep 29
Total with 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! (2,230 reviews)
"Beautiful facility. Unfortunately we arrived after 8 pm and restaurant and bar were closed and are also closed on Monday. I did find it odd that all dining options on site are not available on Mondays. It should be noted that Northampton has lots of dining options, although some are also closed on ..."

Reviewed on Sep 15, 2025

D. Hotel Suites & Spa
See all 471 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.
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Amherst
Stay at this vacation home in Amherst. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Puffers Pond South Beach and Athletic Fields ...
9.8/10 Exceptional! (106 reviews)
"Check in was easy breezy, communication with host was timely and helpful. It was perfect for our two day stay. Fresh eggs and homemade bread and Cushman's cafe close by wwre added treats!"

Reviewed on Aug 4, 2025

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
Stay at this apartment in Lanesborough. Enjoy a garden, an in-room coffeemaker, and in-room fireplaces. Popular attractions Jiminy Peak Mountain Resort and Mount ...
9.6/10 Exceptional! (64 reviews)
Quaint Little Room!
"The room itself was well kept, clean, and had everything we needed!Located right near a coffee house / country store, down the road from Jiminy Peak, and a short drive to some great hiking spots- this is all you need for a weekend getaway!"

Reviewed on Feb 27, 2025

Cozy Rustic Apt in 18th c Berkshire Farmhouse
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Becket
Stay at this cabin in Becket. Enjoy a garden, laundry facilities, and furnished lanais. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
9.6/10 Exceptional! (191 reviews)
"We appreciated how clean and well stocked the cottage was. The owner was very easy to work with. Accurate description of a quiet, secluded get-away in the woods"

Reviewed on Sep 1, 2025

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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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