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Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

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Our top choices for Chester hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is NZ$209
includes taxes & fees
26 May - 27 May
Best Western Plus Berkshire Hills Inn & Suites
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is NZ$207
includes taxes & fees
29 May - 30 May
The Yankee Inn
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very good, (1,002 reviews)
"The breakfast was great! The rooms and hallways could be cleaner."
United States
Rasha
The price is NZ$180
includes taxes & fees
9 June - 10 June
Hampton Inn West Springfield
Standard Room, 2 Queen Beds, Non Smoking

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
8.0 out of 10, Very good, (187 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is NZ$207
includes taxes & fees
28 May - 29 May
Baldwin Inn & Suites, SureStay Collection by Best Western
Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,199 reviews)
"Spacious room, very helpful staff, good coffee and an excellent breakfast."
United States
Clifford
The price is NZ$151
includes taxes & fees
14 June - 15 June
D. Hotel Suites & Spa
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,002 reviews)
"Great location "
United States
Edith
The price is NZ$215
includes taxes & fees
25 May - 26 May
Quality Inn Lee - Lenox South
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,002 reviews)
"It was a great stay."
United States
Geovani
The price is NZ$228
includes taxes & fees
22 June - 23 June
Tru by Hilton Chicopee Springfield
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (643 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is NZ$232
includes taxes & fees
22 June - 23 June
Fairfield Inn & Suites Springfield Holyoke
Studio Suite, Multiple Beds

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (156 reviews)
"Friendly staff, great under the radar spot alternative to chain motels!"
United States
Anthony
The price is NZ$184
includes taxes & fees
26 May - 27 May
River Valley Inn
Room, 2 Queen Beds, Refrigerator

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (860 reviews)
"very friendly, room was nice and breakfast was great"
United States
Lawrence
The price is NZ$224
includes taxes & fees
28 May - 29 May
Hampton Inn Westfield
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (946 reviews)
"Clean and great job staffing "
United States
Pedro
The price is NZ$205
includes taxes & fees
25 May - 26 May
Berkshire Mountain Lodge
Indoor pool

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, (96 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is NZ$249
includes taxes & fees
27 May - 28 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (932 reviews)
"Very clean& maintained. Most comfortable bed I've slept in"
United States
Keith
The price is NZ$185
includes taxes & fees
14 June - 15 June
Quality Inn Westfield - Springfield
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (856 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is NZ$130
includes taxes & fees
28 May - 29 May
Monument Mountain Motel
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is NZ$143
includes taxes & fees
25 May - 26 May
Travelodge by Wyndham Great Barrington Berkshires
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (954 reviews)
The price is NZ$204
includes taxes & fees
26 May - 27 May
Berkshires Untold
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (856 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is NZ$146
includes taxes & fees
25 May - 26 May
Berkshire Inn
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, (876 reviews)
"No issues, reasonable place to stay a night"
Canada
Selwyn
The price is NZ$156
includes taxes & fees
7 June - 8 June
Candlewood Suites West Springfield by IHG
Exterior

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
West Springfield
7.8 out of 10, Good, (1,005 reviews)
"Great stay"
United States
Norbert
The price is NZ$182
includes taxes & fees
28 May - 29 May
Best Western Springfield West Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
The price is NZ$181
includes taxes & fees
11 June - 12 June
The Little Lion
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 Chester attractions

Chester Town Hall

You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping and monuments in Chester!

See all hotels in Chester
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"The room is always clean. We enjoy our stay here every time we visit the Berkshires. We also love the food they serve in the motel restaurant. We love how clean and modern the property looks. Would come back here again when we visit Massachusetts."
Preeyus 2-night trip
Posted 2 hours ago
Berkshires Untold

More cheap accommodation in Chester

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street West Springfield MA
The price is NZ$173 per night from 28 May to 29 May
NZ$173
28 May - 29 May
includes taxes & fees
7/10 Good! (1,004 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Berkshire Mountain Lodge, located 17.2 mi (27.7 km) from the heart of Chester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are Berkshires Untold and Quality Inn West Springfield. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Peace and quiet on the lake: This holiday home rental outside of Chester 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 Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes, the majority of 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 reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer, including the waterfalls, shopping and riverfront. Tourists can also enjoy the city's restaurants, theatres and monuments. There are 879 hotels and other accommodation options in the surrounding area. Find out more about Chester.
What is there to see in Chester?
A favourite place to visit is Chester Town Hall. You'll also find Glendale Falls and Pyramid Lake in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

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