Chesterfield Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chesterfield hotels

Lobby
Hotel UMass

Hotel UMass

2.5 star property
Amherst
8.8 out of 10, Excellent, (1011)
"Great on campus location!"
United States
Shuhui
The price is €108
includes taxes & fees
29 Dec - 30 Dec
Hotel UMass
Balcony
Inn on Boltwood

Inn on Boltwood

3.0 star property
Amherst
9.4 out of 10, Exceptional, (745)
"Such a treat to stay here!"
United States
Elizabeth
Inn on Boltwood
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, (972)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is €89
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very good, (787)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is €70
includes taxes & fees
7 Dec - 8 Dec
Candlewood Suites West Springfield by IHG
Lobby sitting area
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, (62)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is €92
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (801)
"Clean room and staff was super friendly"
United States
Yuen
The price is €128
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (768)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
Basic Studio, 1 King Bed
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (98)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is €105
includes taxes & fees
7 Dec - 8 Dec
River Valley Inn
Lobby
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1004)
"Great like always "
United States
Sharee
The price is €82
includes taxes & fees
8 Dec - 9 Dec
Red Roof Inn PLUS+ West Springfield
Check-in/check-out kiosk
Quality Inn West Springfield

Quality Inn West Springfield

2.5 star property
West Springfield
7.0 out of 10, Good, (1020)
"Room and staff were good "
United States
George
The price is €85
includes taxes & fees
22 Dec - 23 Dec
Quality Inn West Springfield
Property amenity
Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst

3.0 star property
Hadley
9.0 out of 10, Wonderful, (678)
"Nice and quiet and conveniently located very close to UMass"
United States
Connor
The price is €130
includes taxes & fees
7 Dec - 8 Dec
Courtyard by Marriott Hadley Amherst
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2266)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is €86
includes taxes & fees
30 Nov - 1 Dec
D. Hotel Suites & Spa
View from property
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3.0 star property
West Springfield
9.2 out of 10, Wonderful, (571)
"Room was clean and staff was super friendly "
United States
Jessuca
The price is €117
includes taxes & fees
7 Dec - 8 Dec
Courtyard by Marriott West Springfield
Lobby
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
Northampton
9.2 out of 10, Wonderful, (1003)
"Clean room great breakfast selections would stay here again"
United States
Mary
The price is €122
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites Springfield Northampton/Amherst
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

2.5 star property
West Springfield
9.6 out of 10, Exceptional, (94)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is €108
includes taxes & fees
28 Dec - 29 Dec
Blue – A Modern Hotel, an Ascend Collection Hotel
Lobby
Comfort Inn & Suites

Comfort Inn & Suites

2.5 star property
Hadley
9.2 out of 10, Wonderful, (1015)
"Hotel was clean, bed was comfortable, staff was friendly and good breakfast options. "
United States
Brandi
The price is €119
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very good, (1003)
"Clean room and good breakfast "
United States
Kelly
The price is €89
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4.0 star property
Pittsfield
8.6 out of 10, Excellent, (345)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is €86
includes taxes & fees
30 Nov - 1 Dec
The Central Downtown Inn & Suites
Lobby
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 star property
West Springfield
8.2 out of 10, Very good, (1001)
"The staff was absolutely amazing! Close to our event, rooms were clean and everything worked and though there is always that one loud group the staff was sure to address and fix the issue. "
United States
Pamela
The price is €102
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn West Springfield
Desk, laptop workspace, blackout curtains, iron/ironing board
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, (1011)
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
United States
Max
The price is €86
includes taxes & fees
4 Dec - 5 Dec
Red Roof Inn PLUS+ South Deerfield – Amherst
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 forests while you're in the area.
See properties

Chesterfield Public Library

Chesterfield Public Library is just one of the places to see in Chesterfield, so why not enjoy the other things to explore during your travels? Amble around the area's parks or visit its shops.
See properties

Top Chesterfield Hotel Reviews

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

10/10 Excellent
"The room was great. The staff quick and "
Danny 1-night trip
Posted 21 hours ago
Courtyard by Marriott West Springfield

More cheap stays in Chesterfield

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
The price is €85 per night from 22 Dec to 23 Dec
€85
22 Dec - 23 Dec
includes taxes & fees
7/10 Good! (1,014 reviews)

Frequently asked questions

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 traveller data. Two other choices for your visit to the area are D. Hotel Suites & Spa and Quality Inn West Springfield. 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 483 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, Westfield River and Knightville Dam & Reservation. 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.

Explore a world of travel with Expedia