Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from ฿2,218

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29 Oct - 30 Oct
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30 Oct - 31 Oct
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31 Oct - 2 Nov
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7 Nov - 9 Nov

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Top 10 Chester hotels and places to stay

BBQ/picnic Area
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great Indian restaurant in the hotel!"
United States
Chris
The price is ฿3,440
฿3,842 total
includes taxes & fees
5 Nov - 6 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (786)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is ฿2,999
฿3,350 total
includes taxes & fees
4 Nov - 5 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1022)
"Fresh breakfast menu, clean and great location."
United States
Gail
The price is ฿3,470
฿3,876 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (930)
"Friendly staff and clean rooms. Loved the onsite restaurant & bar."
United States
Carmen
The price is ฿3,335
฿3,725 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ฿4,170
฿5,923 total
includes taxes & fees
4 Nov - 5 Nov
The Cornell Inn, Lenox & The Berkshires
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (86)
"Great quiet motel. "
United States
Hector
The price is ฿3,853
฿4,303 total
includes taxes & fees
9 Nov - 10 Nov
River Valley Inn
Exterior
Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
2.5 star property
8.4 out of 10, Very good, (776)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is ฿3,173
฿3,631 total
includes taxes & fees
12 Nov - 13 Nov
Candlewood Suites West Springfield by IHG
Lobby
Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 star property
6.8 out of 10, (1001)
"The staff was very helpful and nice"
United States
Cristal
The price is ฿3,176
฿3,634 total
includes taxes & fees
5 Nov - 6 Nov
Red Roof Inn PLUS+ West Springfield
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (55)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
United States
Marti
The price is ฿4,100
฿4,580 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (740)
"Great stay, perfect "
United States
Lawrence
Berkshire Mountain Lodge
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1022)
"Picture perfect Inn"
United States
jeff
The price is ฿4,824
฿6,835 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (682)
"This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. "
United States
Tina
The price is ฿3,464
฿3,869 total
includes taxes & fees
5 Nov - 6 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (786)
"Clean room, great location. Restaurant phenomenal "
United States
Mary
The price is ฿3,788
฿4,231 total
includes taxes & fees
4 Nov - 5 Nov
Hotel On North
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
7.6 out of 10, Good, (556)
"The staff were very friendly and accommodating "
United States
Tom
The price is ฿2,428
฿2,712 total
includes taxes & fees
3 Nov - 4 Nov
Travelodge by Wyndham Great Barrington Berkshires
Check-in/check-out kiosk
Quality Inn West Springfield
Quality Inn West Springfield
2.5 star property
7.0 out of 10, Good, (1036)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
United States
Danielle
The price is ฿2,614
฿2,992 total
includes taxes & fees
16 Nov - 17 Nov
Quality Inn West Springfield
Property amenity
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
3.5 star property
9.0 out of 10, Wonderful, (773)
"We enjoyed our stay and will definitely be back."
United States
Howard
The price is ฿3,791
฿4,687 total
includes taxes & fees
18 Nov - 19 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
8.2 out of 10, Very good, (1289)
"Great staff, very clean property, and good breakfast. "
United States
Jasmine
The price is ฿3,715
฿4,215 total
includes taxes & fees
9 Nov - 10 Nov
La Quinta Inn & Suites by Wyndham Springfield MA
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (557)
"Everything was very nice. A very simple experience."
United States
Anthony
The price is ฿4,115
฿4,596 total
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (799)
"Good service and people"
United States
Jerod
The price is ฿2,185
฿2,441 total
includes taxes & fees
12 Nov - 13 Nov
FairBridge Inn Express
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (643)
"Staff friendly, room was quiet, large and comfortable. "
United States
Barbara
The price is ฿1,986
฿2,218 total
includes taxes & fees
12 Nov - 13 Nov
Econo Lodge Lee - Great Barrington
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 theatre in Chester!

See all hotels in Chester
Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"Clean and modern. Fancy. "
Andrew 1-night trip
Posted 2 days ago
Blue – A Modern Hotel, an Ascend Collection Hotel

More cheap stays in Chester

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street, West Springfield, MA
The price is ฿3,176 per night from 5 Nov to 6 Nov
฿3,176
฿3,634 total
5 Nov - 6 Nov
includes taxes & fees
6.8/10 (1,004 reviews)

Frequently asked questions

What's the best place to stay in Chester?
La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 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 Berkshire Mountain Lodge 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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