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Go beyond your typical stay in Chesterfield

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Nov 7 - Nov 8
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Our top choices for Chesterfield hotels

A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.

1. Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
3.0 star property
Northampton
9.2 out of 10, Wonderful, (1,006 reviews)
"Nice, clean, room; friendly staff; good breakfast options"
United States
Erik
The price is ₩199,601
₩222,954 total
includes taxes & fees
Nov 16 - Nov 17
Fairfield Inn & Suites Springfield Northampton/Amherst
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.

2. Hotel Northampton

Hotel Northampton
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,001 reviews)
"nice place to stay in the heart of downtown Northampton"
United States
Beth
The price is ₩201,596
₩225,177 total
includes taxes & fees
Nov 12 - Nov 13
Hotel Northampton
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

3. River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (305 reviews)
"Super friendly and helpful staff, convenient parking, decently sized room."
United States
Brandon
The price is ₩127,677
₩142,616 total
includes taxes & fees
Nov 22 - Nov 23
River Valley Inn
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

4. The Ellery

The Ellery
3.5 star property
Northampton
9.4 out of 10, Exceptional, (1,009 reviews)
"great and quaint stay"
United States
Adalie
The price is ₩138,099
₩154,256 total
includes taxes & fees
Dec 7 - Dec 8
The Ellery
A hotel with a covered entrance, a flag, and a clear sky.

5. Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,002 reviews)
"Very clean spacious room and friendly staff. Will definitely stay here again!!"
United States
Jennifer
The price is ₩161,494
₩180,389 total
includes taxes & fees
Dec 1 - Dec 2
Comfort Inn & Suites Hadley - Amherst
A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

6. D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,090 reviews)
"Very comfortable beds nice clean bathroom Excellent hot breakfast"
United States
Luke
The price is ₩159,933
₩187,130 total
includes taxes & fees
Nov 29 - Nov 30
D. Hotel Suites & Spa
A modern kitchen with a central island, a refrigerator, and a coffee station.

7. Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst
2.5 star property
Northampton
7.2 out of 10, Good, (1,001 reviews)
"The hotel is a great place to stay for a trip in this area."
United States
Ni-Ling
The price is ₩160,395
₩179,161 total
includes taxes & fees
Nov 30 - Dec 1
Quality Inn & Suites Northampton - Amherst
A view of a red building by a waterway through a window.

8. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (552 reviews)
"The Old Mill is a great, unique hotel for staying in Western MA. The room was well decorated to match the historic usage of the building. Also, the bed was comfortable and the bathroom was great. It’s very convenient for getting around by I91 and 5&10. The area is beautiful in the fall."
United States
Wayne
The price is ₩243,651
₩272,158 total
includes taxes & fees
Nov 9 - Nov 10
Old Mill Inn
A hotel lobby with a bar area, dining tables, and comfortable seating.

9. Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (1,001 reviews)
"SPacious room, indoor pool, easy drive to Northampton. We enjoyed our stay."
United States
Esther
The price is ₩165,010
₩184,316 total
includes taxes & fees
Nov 17 - Nov 18
Hampton Inn Hadley-Amherst Area
A modern living room with a fireplace, red curtains, and a wooden dining table.

10. Hotel UMass

Hotel UMass
2.5 star property
Amherst
9.0 out of 10, Wonderful, (1,001 reviews)
"Lovely room, great location, staff excellent"
United States
Lyla
The price is ₩129,510
₩146,561 total
includes taxes & fees
Nov 9 - Nov 10
Hotel UMass
A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".

11. Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (900 reviews)
"the wonderful stay!"
United States
Yong
The price is ₩279,791
₩312,527 total
includes taxes & fees
Nov 8 - Nov 9
Inn on Boltwood
A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.

12. Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (709 reviews)
"Super clean room, excellent temperature control wihh the the room a/c. Breakfast was hot and fresh, eggs, sausage, fruit, yogurts, oatmeal with all the toppings"
United States
Caroline
The price is ₩169,830
₩189,700 total
includes taxes & fees
Dec 2 - Dec 3
Fairfield Inn & Suites Springfield Holyoke
A modern hotel lobby with a stone wall, a fireplace, a bar area, and seating arrangements.

13. Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (848 reviews)
"Great breakfast, excellent staff"
United States
Jenny
The price is ₩199,261
₩222,575 total
includes taxes & fees
Dec 1 - Dec 2
Homewood Suites by Hilton Hadley Amherst
An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.

14. Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (787 reviews)
":)"
United States
Eric
The price is ₩243,137
₩271,584 total
includes taxes & fees
Nov 11 - Nov 12
Courtyard by Marriott Hadley Amherst
A hotel reception area with a stone wall, leather chairs, a reception desk, and a sign indicating free Wi-Fi.

15. Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 star property
South Deerfield
7.2 out of 10, Good, (1,007 reviews)
"Room was neat and clean, air conditioning worked great and helped keep the room at a cool temperature. Friendly staff, easy location, a would recommend for a quick stay."
United States
Jack
The price is ₩121,230
₩135,414 total
includes taxes & fees
Dec 6 - Dec 7
Red Roof Inn PLUS+ South Deerfield – Amherst
A modern hotel building with a prominent 'tru' logo, multiple floors, and a covered entrance area.

16. Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,003 reviews)
"Was a great stay, very clean, quiet, and breakfast was good."
United States
Jose
The price is ₩148,855
₩168,876 total
includes taxes & fees
Nov 15 - Nov 16
Tru by Hilton Chicopee Springfield
An outdoor patio area with a circular fire pit surrounded by wicker chairs and tables.

17. TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (113 reviews)
"What a lovely property- such a great place to stay when in the Amherst area - staff is excellent- the rooms are all perfect and the amenities are outstanding"
United States
Sarah
The price is ₩195,012
₩217,828 total
includes taxes & fees
Nov 29 - Nov 30
TownePlace Suites by Marriott Hadley Amherst
A hotel lobby with a reception desk, seating area, and a dining section.

18. Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (933 reviews)
"It was a good family hotel."
United States
Shaleen
The price is ₩152,025
₩169,813 total
includes taxes & fees
Dec 7 - Dec 8
Hampton Inn Westfield
An indoor swimming pool with clear water, surrounded by windows with a view of trees.

19. Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (978 reviews)
"Staff were excellent!!! THANK YOU!"
United States
Quentin
The price is ₩239,336
₩267,338 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn & Suites Greenfield
A historic building with a covered porch, American flags, and a sign reading 'Deerfield Inn.'

20. Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
9.8 out of 10, Exceptional, (40 reviews)
"Excellent stay!"
United States
Debbie
The price is ₩249,246
₩327,931 total
includes taxes & fees
Nov 29 - Nov 30
Deerfield 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.
View all properties

Compare top hotels in Chesterfield

A modern living room with a stone fireplace, a white sofa, a round coffee table, and a green armchair.

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
Northampton
View
A multi-story hotel with a prominent "Hotel Northampton" sign, featuring a classic architectural style with a brick facade and multiple windows.

Hotel Northampton

3.5 star property
Northampton
View
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

River Valley Inn

2.0 star property
West Hatfield
View
A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.

The Ellery

3.5 star property
Northampton
View
A hotel with a covered entrance, a flag, and a clear sky.

Comfort Inn & Suites Hadley - Amherst

2.5 star property
Hadley
View
9.2
Wonderful
1,006 reviews
9.2
Wonderful
1,001 reviews
8.4
Very good
305 reviews
9.4
Exceptional
1,009 reviews
9.2
Wonderful
1,002 reviews
The price is ₩199,601
₩222,954 total
includes taxes & fees
Nov 16 - Nov 17
The price is ₩201,596
₩225,177 total
includes taxes & fees
Nov 12 - Nov 13
The price is ₩127,677
₩142,616 total
includes taxes & fees
Nov 22 - Nov 23
The price is ₩138,099
₩154,256 total
includes taxes & fees
Dec 7 - Dec 8
The price is ₩161,494
₩180,389 total
includes taxes & fees
Dec 1 - Dec 2
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, Parking

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

Top Chesterfield Hotel Reviews

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
The Ellery

The Ellery

The Ellery
Northampton

10/10 Excellent

It’s a great place to stay and we like the breakfast!
United States
Marilyn
Reviewed June 14, 2025
The Ellery

Frequently Asked Questions

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. In Chesterfield, there are 3 hotels and other accommodations to choose from. Find out more about Chesterfield.

What should I see while I'm in Chesterfield?

Natural beauty is on display at Chesterfield Gorge, Oak Hill, and Knightville Dam & Reservation. 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.

Where is the best place to stay in Chesterfield?

Located 21.7 mi (34.9 km) from the heart of Chesterfield, Berkshire Mountain Lodge is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are D. Hotel Suites & Spa and Hampton Inn West Springfield. See all available top hotels, or vacation rentals in Chesterfield.