Find hotels in Chesterfield, MA from ฿2,613

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22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Chesterfield hotels

Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (125)
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
United States
Allison
The price is ฿2,101
฿3,872 total
includes taxes & fees
6 Jan - 7 Jan 2026
Blooming Inn
Front of property – evening/night
Inn on Boltwood

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
Free daily buffet breakfast
Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (904)
"We left too early for breakfast. Parking was fine "
United States
Virginia
The price is ฿2,937
฿3,280 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Westfield - Springfield
Lobby
Hampton Inn Westfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (817)
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is ฿3,624
฿4,048 total
includes taxes & fees
21 Jan - 22 Jan 2026
Hampton Inn Westfield
37-inch LCD TV with cable channels, TV, iPod dock
Hotel UMass

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1007)
"Love staying on campus when we visit!"
United States
Joan
The price is ฿3,909
฿4,402 total
includes taxes & fees
20 Jan - 21 Jan 2026
Hotel UMass
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (68)
"Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!"
United States
Jeanne
The price is ฿3,551
฿3,966 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property amenity
Courtyard by Marriott Hadley Amherst

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 ฿4,491
฿5,017 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Hadley Amherst
Deluxe Room, 1 King Bed | Hypo-allergenic bedding, individually decorated, individually furnished
Black Walnut Inn

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
Lobby
Homewood Suites by Hilton Hadley Amherst

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 ฿4,430
฿4,948 total
includes taxes & fees
5 Jan - 6 Jan 2026
Homewood Suites by Hilton Hadley Amherst
Restaurant
Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (959)
"Great welcome at front desk."
United States
RAYMAN
The price is ฿4,095
฿4,574 total
includes taxes & fees
29 Dec - 30 Dec
Hampton Inn Hadley-Amherst Area
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

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, (143)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is ฿5,408
฿6,041 total
includes taxes & fees
29 Dec - 30 Dec
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

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 ฿4,016
฿4,486 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Lenox Pittsfield
Property amenity
TownePlace Suites by Marriott Hadley Amherst

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 ฿4,629
฿5,170 total
includes taxes & fees
21 Jan - 22 Jan 2026
TownePlace Suites by Marriott Hadley Amherst
Property entrance
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (807)
"Clean room and staff was super friendly"
United States
Yuen
The price is ฿4,637
฿5,180 total
includes taxes & fees
30 Dec - 31 Dec
Hotel On North
Balcony
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (347)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ฿2,926
฿3,268 total
includes taxes & fees
30 Dec - 31 Dec
The Central Downtown Inn & Suites
Exterior
Harbour House Inn

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 ฿6,692
฿7,073 total
includes taxes & fees
21 Jan - 22 Jan 2026
Harbour House Inn
55-inch LCD TV with digital channels, printers
The Revival House

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 ฿4,671
฿5,217 total
includes taxes & fees
29 Dec - 30 Dec
The Revival House
Check-in/check-out kiosk
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (794)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ฿3,100
฿4,164 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge
Exterior
Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1005)
"Good hotel, staff and breakfast. "
United States
Julie
The price is ฿3,890
฿4,345 total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Hadley - Amherst
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

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 ฿2,676
฿2,989 total
includes taxes & fees
24 Dec - 25 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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Stay near popular Chesterfield attractions

Chesterfield Gorge

Explore the great outdoors at Chesterfield Gorge, a lovely green space in Chesterfield. Wander the lakeside and forests while you're in the area.
See properties

Chesterfield Town Hall

After visiting Chesterfield Town Hall, make a plan to see the other sights and activities in Chesterfield. Amble around the area's parks or visit its shops.
See properties

Top Chesterfield Hotel Reviews

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"The staff was courteous and helpful. The room was very clean as was the entire building."
Sylvia 4-night trip
Posted 5 days ago
Tru by Hilton Chicopee Springfield
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Room was clean and neat. Staff was very friendly and professional. Nice amenities - very good free fresh baked cookies, snacks and water, coffee/tea. Nice bathroom. Small fridge- great for leftovers or cooling beverages. Microwave. Excellent tv. Great bed linens. Plenty of towels. Oh, and nice bathrobes and slippers. We definitely will come back. We often hp out to this area. It's good to find a hotel like this. Quiet, but just moments away from dining, shopping, and nearby local activities."
Ingrid 1-night trip
Posted 10 days ago
Blue – A Modern Hotel, an Ascend Collection Hotel

More cheap stays in Chesterfield

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is ฿2,283 per night from 25 Dec to 26 Dec
฿2,283
฿2,613 total
25 Dec - 26 Dec
includes taxes & fees
5.8/10 (999 reviews)

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.
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.