Photo by Elizabeth Massa Peroulakis

Chester hotels from RM371

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Top 10 trending Chester hotels

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, (1000)
"Great Indian restaurant in the hotel!"
The price is RM483
RM539 total
includes taxes & fees
27 Oct - 28 Oct
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (737)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is RM538
RM601 total
includes taxes & fees
2 Oct - 3 Oct
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1014)
"Nice area to visit "
The price is RM488
RM546 total
includes taxes & fees
2 Oct - 3 Oct
The Yankee, Trademark Collection by Wyndham
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, (1000)
"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 RM537
RM764 total
includes taxes & fees
29 Oct - 30 Oct
The Cornell Inn, Lenox & The Berkshires
Red Roof Inn PLUS+ West Springfield
Lobby

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1024)
"Great and what we expected. Clean Room. Awesome beds. Staff was polite. Bathrooms a bit outdated, but great stay for the price."
The price is RM394
RM451 total
includes taxes & fees
14 Oct - 15 Oct
Red Roof Inn PLUS+ West Springfield
River Valley Inn
Desk, laptop workspace, free WiFi, bed sheets

River Valley Inn

2.0 star property
8.6 out of 10, Excellent, (69)
"Great quiet motel. "
The price is RM543
RM606 total
includes taxes & fees
8 Oct - 9 Oct
River Valley Inn
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1010)
"great place have stayed several times, and hope to return."
The price is RM753
RM1,029 total
includes taxes & fees
30 Oct - 31 Oct
The Red Lion Inn
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (549)
"Excellent location, friendly service, clean, comfortable room."
The price is RM316
RM352 total
includes taxes & fees
2 Oct - 3 Oct
Travelodge by Wyndham Great Barrington Berkshires
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, (547)
"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "
The price is RM584
RM652 total
includes taxes & fees
29 Oct - 30 Oct
The Constance by the Lenox Collection
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (776)
"Great property! Very large clean room in a unique hotel! "
The price is RM676
RM755 total
includes taxes & fees
5 Oct - 6 Oct
Hotel On North
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, (741)
"The lodging was convenient to all the area attractions."
The price is RM564
RM689 total
includes taxes & fees
2 Oct - 3 Oct
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (883)
"Our stay was very pleasant "
The price is RM414
RM462 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Econo Lodge Lee - Great Barrington
Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (635)
"This property seemed improved over my last stay. It was clean and convenient for access to the local area amenities. I would stay there the next time I am in the area."
The price is RM283
RM316 total
includes taxes & fees
27 Oct - 28 Oct
Econo Lodge Lee - Great Barrington
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (668)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is RM453
RM600 total
includes taxes & fees
2 Oct - 3 Oct
Berkshire Mountain Lodge
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, (45)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is RM627
RM700 total
includes taxes & fees
2 Oct - 3 Oct
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
La Quinta Inn & Suites by Wyndham Springfield MA
Indoor pool

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
8.2 out of 10, Very good, (1269)
"Affordable and easy access to the Big E. Friendly staff. "
The price is RM501
RM568 total
includes taxes & fees
14 Oct - 15 Oct
La Quinta Inn & Suites by Wyndham Springfield MA
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (666)
"Very Good; Clean, Quiet Motel, Area has many dining options."
The price is RM564
RM630 total
includes taxes & fees
27 Oct - 28 Oct
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (766)
"I would definitely stay here again!"
The price is RM412
RM472 total
includes taxes & fees
26 Oct - 27 Oct
Candlewood Suites West Springfield by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (738)
"Thank you for nice hospity. Staff was very friendly and professional."
The price is RM703
RM785 total
includes taxes & fees
28 Oct - 29 Oct
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (492)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
The price is RM601
RM672 total
includes taxes & fees
3 Oct - 4 Oct
Whistler's Inn Bed & Breakfast
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!

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Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

10/10 Excellent
"We stayed here when we went to an event at the eastern states exposition. It was coles, by so we were able to walk from the hotel to the fairgrounds"
Joe 1-night trip
Posted 1 day ago
Baldwin Inn & Suites, SureStay Collection by Best Western

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 RM354 per night from 12 Oct to 13 Oct
RM354
RM406 total
12 Oct - 13 Oct
includes taxes & fees
7/10 Good! (1,032 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 Red Roof Inn PLUS+ 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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Explore a world of travel with Expedia