Chesterfield hotels from HK$609

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Our top choices for Chesterfield hotels

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (129 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is HK$758
HK$1,228 total
includes taxes & fees
14 Jan - 15 Jan
Blooming Inn

Inn on Boltwood

Inn on Boltwood
3.0 star property
Amherst
9.4 out of 10, Exceptional, (756 reviews)
"Idyllic New England inn…. Cozy, super clean, great restaurant on the property, roaring fireplace, great way to spend weekend with family over the holidays!"
United States
Eileen
The price is HK$1,517
HK$1,695 total
includes taxes & fees
14 Jan - 15 Jan
Inn on Boltwood

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (907 reviews)
"Owner was very rude at check in"
United States
Robert
The price is HK$729
HK$814 total
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Westfield - Springfield

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (821 reviews)
"I will stay again"
United States
Jailene
The price is HK$888
HK$992 total
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn Westfield

Hotel UMass

Hotel UMass
2.5 star property
Amherst
8.8 out of 10, Excellent, (1,002 reviews)
"Love staying on campus when we visit!"
United States
Joan
The price is HK$979
HK$1,102 total
includes taxes & fees
14 Jan - 15 Jan
Hotel UMass

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (73 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is HK$955
HK$1,067 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Courtyard by Marriott Hadley Amherst

Courtyard by Marriott Hadley Amherst
3.0 star property
Hadley
9.0 out of 10, Wonderful, (686 reviews)
"The staff was helpful, available, the gym was clean and easy to use, the rooms were spacious and very clean. Great hotel"
United States
Jan
The price is HK$1,185
HK$1,323 total
includes taxes & fees
25 Jan - 26 Jan
Courtyard by Marriott Hadley Amherst

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
10.0 out of 10, Exceptional, (99 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

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 HK$694
HK$775 total
includes taxes & fees
23 Jan - 24 Jan
Elm Motel

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (723 reviews)
"great location and huge room, very nice hotel suite!"
United States
Lihong
The price is HK$1,080
HK$1,207 total
includes taxes & fees
10 Feb - 11 Feb
Homewood Suites by Hilton Hadley Amherst

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (968 reviews)
"Staff was very friendly, room very clean"
United States
Christine
The price is HK$1,004
HK$1,122 total
includes taxes & fees
12 Feb - 13 Feb
Hampton Inn Hadley-Amherst Area

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 HK$1,354
HK$1,513 total
includes taxes & fees
14 Jan - 15 Jan
The Trail in Adams - Berkshires’ Art Hotel

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is HK$997
HK$1,113 total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (60 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 HK$1,159
HK$1,295 total
includes taxes & fees
22 Jan - 23 Jan
TownePlace Suites by Marriott Hadley Amherst

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (815 reviews)
"Great staff, room was huge and comfortable. "
United States
Cameron
The price is HK$1,161
HK$1,297 total
includes taxes & fees
15 Jan - 16 Jan
Hotel On North

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (354 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is HK$733
HK$818 total
includes taxes & fees
25 Jan - 26 Jan
The Central Downtown Inn & Suites

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 HK$1,676
HK$1,771 total
includes taxes & fees
15 Jan - 16 Jan
Harbour House Inn

The Revival House

The Revival House
3.0 star property
Adams
9.0 out of 10, Wonderful, (25 reviews)
"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 HK$1,170
HK$1,307 total
includes taxes & fees
18 Jan - 19 Jan
The Revival House

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (810 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is HK$769
HK$1,033 total
includes taxes & fees
8 Feb - 9 Feb
Berkshire Mountain Lodge

Comfort Inn & Suites Hadley - Amherst

Comfort Inn & Suites Hadley - Amherst
2.5 star property
Hadley
9.2 out of 10, Wonderful, (1,003 reviews)
"Clean room, great staff, and good options for breakfast."
United States
nancy
The price is HK$899
HK$1,004 total
includes taxes & fees
12 Feb - 13 Feb
Comfort Inn & Suites Hadley - 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.
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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 traveller data. Two other choices for your visit to the area are Holiday Inn & Suites Pittsfield-Berkshires by IHG 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?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Chesterfield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. 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 487 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, Knightville Dam & Reservation and Westfield River. A couple of additional sights to add to your itinerary are Krug Sugarbush 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.

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