Chesterfield Hotels from S$114

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Top 10 trending Chesterfield hotels

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2263)
"Great hospitality and very pretty hotel and grounds"
D. Hotel Suites & Spa

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is S$269
includes taxes & fees
21 Jul - 22 Jul
Hotel On North

Inn on Boltwood

3.0 star property
9.4 out of 10, Exceptional, (665)
"Beautiful historic inn"
The price is S$1,000
includes taxes & fees
19 Jul - 20 Jul
Inn on Boltwood

Black Walnut Inn

2.0 star property
9.8 out of 10, Exceptional, (74)
"wonderful cooked to order breakfast quiet very kind staff"
The price is S$298
includes taxes & fees
8 Jul - 9 Jul
Black Walnut Inn

Hotel Northampton

3.5 star property
9.2 out of 10, Wonderful, (1006)
"Convenient location, friendly staff, nice bar/restaurants."
Hotel Northampton

Hotel UMass

2.5 star property
8.8 out of 10, Excellent, (997)
"Great hotel! "
Hotel UMass

Fairfield Inn & Suites Springfield Holyoke

2.5 star property
9.2 out of 10, Wonderful, (537)
"Very nice and clean hotel."
The price is S$168
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites Springfield Holyoke

Residence Inn Springfield Chicopee

3.0 star property
9.2 out of 10, Wonderful, (410)
"Absolutely loved our stay! The staff were exceptional, providing a warm welcome and outstanding service. Our room was fantastic! The amenities were top-notch, making our experience truly enjoyable. Highly recommend!"
The price is S$232
includes taxes & fees
27 Jul - 28 Jul
Residence Inn Springfield Chicopee

Hampton Inn Westfield

2.5 star property
8.4 out of 10, Very good, (745)
"It was clean & quiet. The breakfast buffet was very much appreciated "
The price is S$189
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Westfield

Courtyard by Marriott Hadley Amherst

3.0 star property
9.0 out of 10, Wonderful, (626)
"Room is clean, staff is so friendly "
The price is S$229
includes taxes & fees
13 Jul - 14 Jul
Courtyard by Marriott Hadley Amherst

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (294)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is S$169
includes taxes & fees
14 Jul - 15 Jul
The Central Downtown Inn & Suites

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (101)
"Great Place to stay in Small town"
The price is S$175
includes taxes & fees
9 Jul - 10 Jul
Blooming Inn

The Revival House

3.0 star property
10.0 out of 10, Exceptional, (3)
"The Revival House was charming and quiet. It had everything we needed for our short stay. It's only a 6 minute drive to the Bellows Pipe Trail/Mount Greylock, which was a huge plus for us. Wishing all the best for this newly opened hotel!"
The price is S$256
includes taxes & fees
8 Jul - 9 Jul
The Revival House

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (504)
"We enjoyed our stay here. It was very quiet, and had everything we needed."
Berkshire Mountain Lodge

TownePlace Suites by Marriott Hadley Amherst

3.0 star property
9.6 out of 10, Exceptional, (32)
"It was a beautiful property."
The price is S$255
includes taxes & fees
3 Aug - 4 Aug
TownePlace Suites by Marriott Hadley Amherst

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (727)
"A bit older facilities but otherwise meets all the basic needs and is easy on and off the 91 highway "
The price is S$136
includes taxes & fees
3 Aug - 4 Aug
Candlewood Suites West Springfield by IHG

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1004)
"This is a great place to stay and a very convenient location. Lots of shopping for essentials and the Munich haus had a very good diner! "
The price is S$156
includes taxes & fees
13 Jul - 14 Jul
Tru by Hilton Chicopee Springfield

Hampton Inn Hadley-Amherst Area

2.5 star property
9.0 out of 10, Wonderful, (914)
"Clean with friendly and helpful staff. "
The price is S$217
includes taxes & fees
15 Jul - 16 Jul
Hampton Inn Hadley-Amherst Area

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (813)
"Excellent service "
The price is S$229
includes taxes & fees
13 Jul - 14 Jul
Hampton Inn & Suites Greenfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (636)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is S$320
includes taxes & fees
13 Jul - 14 Jul
Hilton Garden Inn Lenox Pittsfield
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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Learn more about Chesterfield

Get away to Chesterfield! Enjoy the adventure, local cuisine and parks.

Frequently asked questions

Where is the best place to stay in Chesterfield?

Located 20.7 mi (33.3 km) from the heart of Chesterfield, Quality Inn West Springfield is a top choice for your stay, based on our traveller data. Two other choices for your visit to the area are Comfort Inn & Suites and Red Roof Inn PLUS+ West Springfield. 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 are some accommodation options with pools in Chesterfield?

D. Hotel Suites & Spa: 3-star hotel located near Mount Holyoke College. Offers 2 restaurants, an indoor pool and a full-service spa. Tru by Hilton Chicopee Springfield and Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel are two additional hotels with an on-site pool.

What is staying in Chesterfield like?

Visitors can enjoy all that Chesterfield has to offer, including the restaurants, shopping and parks. There are 465 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 Silvio O. Conte National Fish and Wildlife Refuge and Chesterfield Public Library. 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.