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6 Feb - 7 Feb
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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)
  • cleanliness
    Discover riverside charm in Shelburne Falls with free WiFi and winter activities.
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is NZ$252
includes taxes & fees
8 Feb - 9 Feb
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, (912 reviews)
  • cleanliness
    Quality Inn offering a serene stay in Westfield with complimentary amenities.
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is NZ$164
includes taxes & fees
27 Feb - 28 Feb
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)
  • cleanliness
    Enjoy a peaceful stay near Big E with an indoor pool and helpful service.
"I will stay again"
United States
Jailene
The price is NZ$232
includes taxes & fees
26 Feb - 27 Feb
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)
  • cleanliness
    Timeless American elegance at the heart of college town charm and culture.
"It is a beautiful and historic property with an amazing restaurant and bar."
United States
Kelly
The price is NZ$384
includes taxes & fees
8 Mar - 9 Mar
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)
  • cleanliness
    Relax in the heart of the Berkshires with an indoor pool and spa pool after a day out.
"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 NZ$246
includes taxes & fees
9 Mar - 10 Mar
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)
  • cleanliness
    Steps from UMass Amherst, enjoy modern rooms and campus views in a prime location.
"Great stay "
United States
Kyle
The price is NZ$236
includes taxes & fees
8 Feb - 9 Feb
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)
  • cleanliness
    Perfect setting for a Berkshires visit with an indoor pool and Asian dining.
" Nice staff - beautiful hotel!"
United States
MARY
The price is NZ$254
includes taxes & fees
8 Mar - 9 Mar
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)
  • cleanliness
    Convenient campus access with cosy indoor pool and American cuisine.
"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 NZ$266
includes taxes & fees
18 Feb - 19 Feb
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, (730 reviews)
  • cleanliness
    Modern hotel near UMass with pool, ideal for comfortable extended stays.
"The room was efficient, clean and spacious. The pool was great and so was the breakfast. "
United States
Julianne
The price is NZ$261
includes taxes & fees
5 Mar - 6 Mar
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)
  • cleanliness
    Explore city centre Pittsfield from a stylish hotel with complimentary WiFi and parking.
"Great staff, beautiful hotel. Would definitely recommend "
United States
Shawn
The price is NZ$278
includes taxes & fees
19 Feb - 20 Feb
Hotel On North
Lobby

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
  • cleanliness
    Comfortable motel near Big E with convenient parking and 24/7 service.
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is NZ$186
includes taxes & fees
24 Feb - 25 Feb
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)
  • cleanliness
    Serene stays near University of Massachusetts with indoor pool and free breakfast.
"Best hotel in the area, hands down"
United States
alexander
The price is NZ$234
includes taxes & fees
18 Feb - 19 Feb
Hampton Inn Hadley-Amherst Area
Exterior

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 NZ$188
includes taxes & fees
8 Mar - 9 Mar
The Central Downtown Inn & Suites
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (829 reviews)
  • cleanliness
    Experience the beauty of the Berkshires at a cosy lodge with golf access and pool.
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is NZ$223
includes taxes & fees
8 Feb - 9 Feb
Berkshire Mountain Lodge
Deluxe Room, 1 King Bed

Black Walnut Inn

Black Walnut Inn
2.0 star property
North Amherst
9.8 out of 10, Exceptional, (102 reviews)
  • cleanliness
    Cosy B&B close to UMass Amherst with complimentary breakfast and hiking trails.
"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)
  • cleanliness
    Take in art and nature steps from the Berkshires' best hiking trails and museums.
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is NZ$324
includes taxes & fees
9 Mar - 10 Mar
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)
  • cleanliness
    Discover a comfortable stay near UMass Amherst with indoor pool and fitness access.
"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 NZ$293
includes taxes & fees
18 Feb - 19 Feb
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)
  • cleanliness
    Enjoy a tranquil stay near Tanglewood Music Centre with a refreshing pool.
"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 NZ$157
includes taxes & fees
9 Mar - 10 Mar
Berkshire Inn
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
  • cleanliness
    Serene lakeside B&B near charming Adams Theatre with complimentary full breakfast.
"Nice place for a weekend away."
United States
Gregory
The price is NZ$379
includes taxes & fees
9 Mar - 10 Mar
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)
  • cleanliness
    Serene retreat in Pittsfield with indoor pool and tranquil rooms near Tanglewood.
"Staff was very courteous and rooms clean."
United States
Steven
The price is NZ$190
includes taxes & fees
7 Mar - 8 Mar
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.
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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

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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Great service, clean & quiet rooms, and a solid breakfast to start the day"
Stephanie 2-night trip
Posted 4 days ago
D. Hotel Suites & Spa

More cheap accommodation in Chesterfield

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is NZ$131 per night from 26 Feb to 27 Feb
NZ$131
26 Feb - 27 Feb
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 traveller data. Two other choices for your visit 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.
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 506 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 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.

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