Photo by Elizabeth Massa Peroulakis

Chester Hotels from S$89

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20 Sept - 21 Sept
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26 Sept - 28 Sept
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Top 10 trending Chester hotels

Our top choices for Chester hotels

Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (771)
"Hotel on North punches above its weight. It's a great hotel in an OK downtown. "
The price is S$228
includes taxes & fees
28 Sept - 29 Sept
Hotel On North
The Ellery
Lobby

The Ellery

3.5 star property
9.2 out of 10, Wonderful, (819)
"Wonderful place! We always stay there if we can!"
The price is S$176
includes taxes & fees
29 Sept - 30 Sept
The Ellery
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (733)
"The lodging was convenient to all the area attractions."
The price is S$185
includes taxes & fees
23 Sept - 24 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1004)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is S$217
includes taxes & fees
22 Sept - 23 Sept
The Cornell Inn, Lenox & The Berkshires
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (726)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise "
The price is S$171
includes taxes & fees
25 Sept - 26 Sept
Berkshires Untold
Brook Farm Inn
1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Hotel Northampton
2 restaurants, breakfast, lunch, dinner served; American cuisine

Hotel Northampton

3.5 star property
9.2 out of 10, Wonderful, (1008)
"Beautiful historic property with great dining options."
Hotel Northampton
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (649)
"Clean, bright, great value, love the hot tub and pool!"
The price is S$162
includes taxes & fees
21 Sept - 22 Sept
Berkshire Mountain Lodge
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (319)
"Nice place "
The price is S$149
includes taxes & fees
1 Oct - 2 Oct
The Central Downtown Inn & Suites
D. Hotel Suites & Spa
Indoor pool

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2238)
"Safe area and clean hotel."
The price is S$193
includes taxes & fees
28 Sept - 29 Sept
D. Hotel Suites & Spa
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is S$481
includes taxes & fees
6 Oct - 7 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Monument Mountain Motel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (754)
"Good value for the price"
Monument Mountain Motel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1010)
"The staff and location make it excellent"
The price is S$182
includes taxes & fees
28 Sept - 29 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Courtyard by Marriott West Springfield
View from property

Courtyard by Marriott West Springfield

3.0 star property
9.2 out of 10, Wonderful, (521)
"Exceptionally satisfying stay in all aspects "
The price is S$219
includes taxes & fees
5 Oct - 6 Oct
Courtyard by Marriott West Springfield
TownePlace Suites by Marriott Hadley Amherst
Property amenity

TownePlace Suites by Marriott Hadley Amherst

3.0 star property
9.8 out of 10, Exceptional, (44)
"I had a great stay for five nights. It a brand new hotel. Everything is clean and quiet. Very friendly staff."
The price is S$264
includes taxes & fees
28 Sept - 29 Sept
TownePlace Suites by Marriott Hadley Amherst
Fairfield Inn & Suites Springfield Northampton/Amherst
Lobby

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
9.2 out of 10, Wonderful, (988)
"Clean room and convenient location "
The price is S$225
includes taxes & fees
28 Sept - 29 Sept
Fairfield Inn & Suites Springfield Northampton/Amherst
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (645)
"We always stay at the Garden Inn when visiting the Berkshires."
The price is S$228
includes taxes & fees
22 Sept - 23 Sept
Hilton Garden Inn Lenox Pittsfield
The Constance by the Lenox Collection
Front of property

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (545)
"Great place , love it, will return"
The price is S$215
includes taxes & fees
23 Sept - 24 Sept
The Constance by the Lenox Collection
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (574)
"Fabulous place"
The price is S$231
includes taxes & fees
29 Sept - 30 Sept
Courtyard by Marriott Lenox Berkshires
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (40)
"Hotel was clean, the rooms had good space, the breakfast was excellent and the team there was very friendly and accommodating "
The price is S$181
includes taxes & fees
24 Sept - 25 Sept
Holiday Inn Express & 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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Learn more about Chester

Experience the hiking, camping and waterfalls in Chester!

See all hotels in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience."
SABRINA 5-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Chester

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is S$146 per night from 2 Oct to 3 Oct
S$146
2 Oct - 3 Oct
includes taxes & fees
7/10 Good! (1,023 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 La Quinta Inn & Suites by Wyndham Springfield MA and Quality Inn West Springfield. See all available top hotels, or 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. In Chester, there are 2 hotels and other accommodation options to choose from. 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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