Find hotels in Chesterfield, MA from ₩121,735

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Feb 5 - Feb 6
Tomorrow
Feb 6 - Feb 7
This weekend
Feb 6 - Feb 8
Next weekend
Feb 13 - Feb 15

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chesterfield hotels

Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is ₩131,500
₩218,479 total
includes taxes & fees
Feb 8 - Feb 9
Blooming Inn
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (911 reviews)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is ₩127,482
₩142,396 total
includes taxes & fees
Feb 27 - Feb 28
Quality Inn Westfield - Springfield
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very Good, (825 reviews)
"I will stay again"
United States
Jailene
The price is ₩178,869
₩199,797 total
includes taxes & fees
Feb 26 - Feb 27
Hampton Inn Westfield
Front of property - evening/night

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (762 reviews)
"It is a beautiful and historic property with an amazing restaurant and bar."
United States
Kelly
The price is ₩298,866
₩333,833 total
includes taxes & fees
Feb 9 - Feb 10
Inn on Boltwood
Indoor pool

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, (81 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is ₩192,940
₩215,514 total
includes taxes & fees
Feb 26 - Feb 27
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
37-inch LCD TV with cable channels, TV, iPod dock

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,003 reviews)
"Friendly staff, access to a meal during a snowstorm, under-roof parking also during a snowstorm and a very clean room."
United States
Kevin
The price is ₩182,147
₩205,078 total
includes taxes & fees
Feb 9 - Feb 10
Hotel UMass
Breakfast, lunch and dinner served

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (665 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ₩200,289
₩223,711 total
includes taxes & fees
Feb 27 - Feb 28
Hilton Garden Inn Lenox Pittsfield
Property amenity

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (690 reviews)
"My son and I stayed during a big snow storm, staff not only got us checked in early but were super friendly and helpful. Hotel was also relatively spotless and clean given the circumstances with the storm."
United States
William
The price is ₩207,364
₩231,625 total
includes taxes & fees
Feb 11 - Feb 12
Courtyard by Marriott Hadley Amherst
Lobby

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (728 reviews)
"The room was efficient, clean and spacious. The pool was great and so was the breakfast. "
United States
Julianne
The price is ₩202,144
₩225,796 total
includes taxes & fees
Feb 11 - Feb 12
Homewood Suites by Hilton Hadley Amherst
Property entrance

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (821 reviews)
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is ₩216,065
₩241,340 total
includes taxes & fees
Feb 8 - Feb 9
Hotel On North
Lobby

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is ₩144,650
₩161,570 total
includes taxes & fees
Feb 24 - Feb 25
Elm Motel
Restaurant

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (975 reviews)
"Best hotel in the area, hands down"
United States
alexander
The price is ₩179,551
₩200,559 total
includes taxes & fees
Feb 18 - Feb 19
Hampton Inn Hadley-Amherst Area
50-inch flat-screen TV with cable channels, TV, streaming services

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (355 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ₩147,572
₩164,842 total
includes taxes & fees
Mar 1 - Mar 2
The Central Downtown Inn & Suites
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (827 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is ₩143,103
₩192,242 total
includes taxes & fees
Feb 10 - Feb 11
Berkshire Mountain Lodge
Deluxe Room, 1 King Bed | Hypo-allergenic bedding, individually decorated, individually furnished

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (101 reviews)
"Enjoyable stay with a warm environment. Enjoyed the breakfast which was well prepared based on my order choice and request. Would stay again!"
United States
Karri
Black Walnut Inn
Terrace/patio

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, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is ₩251,955
₩281,433 total
includes taxes & fees
Feb 6 - Feb 7
The Trail in Adams - Berkshires’ Art Hotel
Property amenity

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (62 reviews)
"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 ₩215,659
₩240,890 total
includes taxes & fees
Feb 11 - Feb 12
TownePlace Suites by Marriott Hadley Amherst
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (842 reviews)
"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 ₩124,694
₩139,282 total
includes taxes & fees
Feb 8 - Feb 9
Berkshire Inn
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is ₩311,772
₩329,550 total
includes taxes & fees
Feb 18 - Feb 19
Harbour House Inn
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,001 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is ₩149,033
₩166,464 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

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.
See properties

Top Chesterfield Hotel Reviews

Hotel Northampton

Hotel Northampton

10/10 Excellent
"The staff were amazing and the room was perfect. "
Shaun 2-night trip
Posted 4 days ago
Hotel Northampton

More cheap stays in Chesterfield

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is ₩106,365 per night from Feb 17 to Feb 18
₩106,365
₩121,735 total
Feb 17 - Feb 18
includes taxes & fees
5.8/10 (1,000 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 Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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, 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 506 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, Knightville Dam & 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.