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Our top choices for Chesterfield hotels

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (124)
"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
United States
Ben
The price is AU$185
includes taxes & fees
4 Jan - 5 Jan 2026
Blooming Inn

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (751)
"Room was clean and the bed was very comfortable. "
United States
Michael
Inn on Boltwood

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (903)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is AU$155
includes taxes & fees
12 Jan - 13 Jan 2026
Quality Inn Westfield - Springfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (816)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is AU$195
includes taxes & fees
21 Jan - 22 Jan 2026
Hampton Inn Westfield

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1006)
"Love staying on campus when we visit!"
United States
Joan
The price is AU$214
includes taxes & fees
22 Dec - 23 Dec
Hotel UMass

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (67)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AU$191
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (682)
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
The price is AU$228
includes taxes & fees
25 Dec - 26 Dec
Courtyard by Marriott Hadley Amherst

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
10.0 out of 10, Exceptional, (98)
"Was a wonderful inn and breakfast absolutely delicious!"
United States
Valerie
Black Walnut Inn

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (715)
"great location and huge room, very nice hotel suite!"
United States
Lihong
The price is AU$238
includes taxes & fees
5 Jan - 6 Jan 2026
Homewood Suites by Hilton Hadley Amherst

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (958)
"Great welcome at front desk."
United States
RAYMAN
The price is AU$208
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn Hadley-Amherst Area

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is AU$294
includes taxes & fees
22 Dec - 23 Dec
The Trail in Adams - Berkshires’ Art Hotel

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is AU$216
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Lenox Pittsfield

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (58)
"The property is very clean and pet friendly. The staff were very friendly and professional. I will definitely stay here again."
United States
Diana
The price is AU$251
includes taxes & fees
28 Dec - 29 Dec
TownePlace Suites by Marriott Hadley Amherst

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (805)
"Clean room and staff was super friendly"
United States
Yuen
The price is AU$252
includes taxes & fees
22 Dec - 23 Dec
Hotel On North

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AU$159
includes taxes & fees
23 Dec - 24 Dec
The Central Downtown Inn & Suites

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is AU$344
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25)
"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "
United States
melissa
The price is AU$254
includes taxes & fees
22 Dec - 23 Dec
The Revival House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (793)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is AU$201
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1004)
"Good hotel, staff and breakfast. "
United States
Julie
The price is AU$209
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Hadley - Amherst

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is AU$134
includes taxes & fees
23 Dec - 24 Dec
Berkshire Inn
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.
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Frequently asked questions

Where is the best place to stay in Chesterfield?
Located 14.5 mi (23.3 km) from the heart of Chesterfield, D. Hotel Suites & Spa is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are Holiday Inn & Suites Pittsfield-Berkshires by IHG and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Chesterfield.
What are some of the best holiday rentals that Chesterfield has to offer?
Peace and quiet on the lake: This holiday home rental outside of Chesterfield is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. See all vacation rentals in Chesterfield.
If I need to cancel my hotel reservation in Chesterfield, will I receive a refund?
Yes, you'll find most hotel room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.
What is staying in Chesterfield like?
Visitors can enjoy all that Chesterfield has to offer, including the restaurants, shopping and parks. There are 487 hotels and other accommodation options in the surrounding area. Find out more about Chesterfield.
What should I do while I'm visiting Chesterfield?
Natural beauty is on display at Chesterfield Gorge, Chesterfield Gorge Reservation and Westfield River. A couple of additional sights to add to your itinerary are Chesterfield Public Library and Chesterfield Town Hall. Take a look at what more there is to see and do in Expedia's Chesterfield guide.
What's the seasonal weather in Chesterfield?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterfield are January, February, November and March, with each month seeing an average of 16 cm of snowfall.

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