Find hotels in Chesterfield, MA from ￥12,449

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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, (124)
Explore Glacial Potholes from this welcoming guesthouse offering snowshoeing, sledding, and snowmobiling on site. Enjoy daily housekeeping and easy access to local attractions like the Shelburne Falls Bowling Alley, with Greenfield Station just a 16-minute drive away.
"Excellent! Really fun space with beautiful objects all around you. One of a kind, well run, seamless experience. "
United States
Ben
The price is ￥10,222
￥19,148 total
includes taxes & fees
Jan 5 - Jan 6, 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)
Savor Colonial sophistication at this Amherst hotel with a rooftop terrace overlooking the historic campus. Just minutes from Emily Dickinson Museum, enjoy American cuisine at 30Boltwood restaurant, relax in the garden, or stroll to nearby cultural attractions.
"Room was clean and the bed was very comfortable. "
United States
Michael
The price is ￥28,253
￥31,559 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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, (903)
Enjoy peaceful accommodations praised by travelers for their quiet atmosphere. This business-friendly hotel provides free breakfast, WiFi, and parking, with helpful staff ready to assist. Conveniently located near General Wareham Park and Gateway Entrance Park.
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is ￥14,496
￥16,192 total
includes taxes & fees
Jan 12 - Jan 13, 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, (816)
Located in Westfield, this hotel offers a complimentary breakfast that guests rave about. Take a refreshing dip in the indoor pool, work out in the fitness center, or visit nearby General Wareham Park. Free WiFi and parking add convenience.
"Very pet friendly and the night check in agent was super kind and friendly"
United States
olivia townsend
The price is ￥18,237
￥20,371 total
includes taxes & fees
Jan 21 - Jan 22, 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, (1006)
Located on UMass Amherst campus, this hotel offers convenient access to Amherst College just 5 minutes away. Enjoy free breakfast, WiFi, and room service before exploring nearby Mullins Center and Fine Arts Center. The Commonwealth restaurant and bar/lounge serve lunch and dinner.
"Love staying on campus when we visit!"
United States
Joan
The price is ￥19,815
￥22,311 total
includes taxes & fees
Dec 22 - Dec 23
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, (67)
Located 10 minutes from Tanglewood Music Center, this hotel provides complimentary breakfast, WiFi, and parking. After exploring nearby attractions, unwind in the indoor pool or soothing hot tub for a peaceful end to your Pittsfield adventure.
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ￥17,834
￥19,921 total
includes taxes & fees
Jan 4 - Jan 5, 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)
Within a 5-minute drive of University of Massachusetts Amherst, this hotel offers The Cafe for tasty American meals. Unwind in the indoor pool, grab drinks at the bar, and stay fit in the 24-hour gym, all backed by a notably helpful staff.
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
The price is ￥21,320
￥23,815 total
includes taxes & fees
Dec 24 - Dec 25
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)
Charming inn offering free full breakfast, WiFi, and parking, just 5 minutes from UMass Amherst. Adventure awaits on nearby hiking and biking trails, while Puffers Pond South Beach provides scenic relaxation after a day of exploration.
"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)
Hadley's Homewood Suites offers spacious rooms near University of Massachusetts Amherst. Guests love the helpful staff, indoor pool, and fitness center. Enjoy free breakfast, WiFi, and parking while exploring nearby Autobahn and Cinemark At Hampshire Mall.
"great location and huge room, very nice hotel suite!"
United States
Lihong
The price is ￥22,249
￥24,852 total
includes taxes & fees
Jan 5 - Jan 6, 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, (957)
Discover this Hadley hotel with an indoor pool for morning swims, just minutes from UMass Amherst. Guests love the helpful staff and clean rooms. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby Hadley Farm Museum.
"Great welcome at front desk."
United States
RAYMAN
The price is ￥19,504
￥21,786 total
includes taxes & fees
Dec 28 - Dec 29
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, (142)
Immerse yourself in this artistic B&B offering hiking trails right from the property. Close to Adams Theater and the Berkshire Scenic Railway Museum, this boutique hotel provides free WiFi, parking, and daily housekeeping.
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is ￥27,409
￥30,616 total
includes taxes & fees
Dec 22 - Dec 23
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, (658)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness center. Enjoy meals at Jae's Asian Fusion restaurant and bar, plus in-room refrigerators and microwaves. Nearby attractions include Herman Melville's Arrowhead and Guido's Marketplace.
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ￥20,173
￥22,533 total
includes taxes & fees
Jan 2 - Jan 3, 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)
This business-friendly hotel offers all-day swimming in the indoor pool and 24-hour fitness center access. Just a short drive from UMass Amherst, it provides free breakfast, WiFi, and parking for a convenient stay near local attractions.
"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 ￥23,461
￥26,207 total
includes taxes & fees
Dec 28 - Dec 29
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, (805)
Minutes from Barrington Stage Company and Berkshire Athenaeum, this hotel offers comfortable rooms and attentive service. Just a 2-minute walk from Pittsfield Intermodal Transportation Center, enjoy room service and the convenient downtown location.
"Clean room and staff was super friendly"
United States
Yuen
The price is ￥23,505
￥26,255 total
includes taxes & fees
Dec 22 - Dec 23
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, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ￥14,087
￥15,735 total
includes taxes & fees
Dec 22 - Dec 23
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)
Unwind at this cozy Cheshire inn offering free WiFi and parking. Explore nearby Mount Greylock State Reservation or catch a show at Adams Theater, then return to comfortable accommodations just 16 minutes from Pittsfield Station.
"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 ￥33,916
￥35,850 total
includes taxes & fees
Jan 7 - Jan 8, 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)
Unwind at this charming guesthouse offering free perks including WiFi, parking, and daily breakfast. Located near Adams Theater and Berkshire Scenic Railway Museum, this cozy retreat provides a perfect base for exploring local attractions.
"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 ￥23,675
￥26,444 total
includes taxes & fees
Dec 22 - Dec 23
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, (793)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ￥15,567
￥20,913 total
includes taxes & fees
Jan 11 - Jan 12, 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, (1003)
Just 5 minutes from UMass Amherst, this hotel offers an indoor pool for year-round swimming and convenient fitness center. Guests praise the free breakfast, helpful staff, and comfortable beds. Explore nearby attractions like Autobahn and Cinemark At Hampshire Mall.
"Good hotel, staff and breakfast. "
United States
Julie
The price is ￥19,537
￥21,823 total
includes taxes & fees
Dec 28 - Dec 29
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 peaceful motel offers a seasonal outdoor pool and clean rooms just 15 minutes from Tanglewood Music Center. Close to Colonial Theater and Berkshire Museum, with free WiFi and parking. Guests praise the helpful staff and quiet, relaxing atmosphere.
"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 ￥13,158
￥14,697 total
includes taxes & fees
Dec 28 - Dec 29
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 forest 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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Spacious room and loved pool and hot tub!"
Deanna 5-night trip
Posted 2 days ago
Berkshire Mountain Lodge

More cheap stays in Chesterfield

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is ￥10,878 per night from Dec 28 to Dec 29
￥10,878
￥12,449 total
Dec 28 - Dec 29
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 traveler data. Other good choices for your trip 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 vacation rentals that Chesterfield has to offer?
Peace and quiet on the lake: Visitors like this Chesterfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection 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, most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chesterfield.
Where can I learn more about changing or cancelling my trip to Chesterfield?
For additional details about rescheduling or cancelling your trip to Chesterfield, click here.
Where is the best place to stay close to Chesterfield Gorge?
Fiddlehead Inn is one of the top choices for your stay based on our traveler data, and this 3-star inn offers a restaurant and free parking. It's located 2.9 mi (4.7 km) from Chesterfield Gorge. Another good choice is Charming Farmhouse - quiet, private & peaceful, located 3 mi (4.9 km) away.
What's the best hotel for staying near Logan International Airport (BOS)?
Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.
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 accommodations in the surrounding area. Find out more about Chesterfield.
What should I see while I'm in Chesterfield?
Natural beauty is on display at Chesterfield Gorge, Chesterfield Gorge Reservation, and Westfield River. A couple of additional sights to add to your agenda are Chesterfield Public Library and Chesterfield Town Hall. Check out what more to see and do in Expedia's Chesterfield guide.
What's the weather like in Chesterfield?
The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

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