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Find hotels in Chester, MA from ₩99,889

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Oct 13 - Oct 14
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Oct 14 - Oct 15
This weekend
Oct 17 - Oct 19
Next weekend
Oct 24 - Oct 26

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Compare 834 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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, (1006)
"Great Indian restaurant in the hotel!"
The price is ₩151,565
₩169,298 total
includes taxes & fees
Nov 2 - Nov 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
Interior
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (756)
"Easy parking, great community spaces, beautiful decor! "
The price is ₩124,817
₩139,421 total
includes taxes & fees
Nov 2 - Nov 3
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, (1006)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
The price is ₩191,292
₩213,674 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
Red Roof Inn PLUS+ West Springfield
Lobby
Red Roof Inn PLUS+ West Springfield
2.5 star property
7.0 out of 10, Good, (1010)
"The staff was very helpful and nice"
The price is ₩139,926
₩160,146 total
includes taxes & fees
Nov 2 - Nov 3
Red Roof Inn PLUS+ West Springfield
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, (1005)
"Very friendly staff. "
The price is ₩182,134
₩259,213 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
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, (898)
"Excellent customer service and great rooms"
The price is ₩146,928
₩164,118 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
River Valley Inn
Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (75)
"Great quiet motel. "
The price is ₩169,752
₩189,613 total
includes taxes & fees
Nov 9 - Nov 10
River Valley Inn
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (53)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is ₩170,038
₩189,923 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (754)
"Lovely spot, great accommodations, friendly staff, and great location."
The price is ₩165,615
₩204,906 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hotel On North
Front of property - evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (779)
"Great property! Very large clean room in a unique hotel! "
The price is ₩167,299
₩186,870 total
includes taxes & fees
Nov 11 - Nov 12
Hotel On North
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (698)
"Great stay, perfect "
The price is ₩132,953
₩180,376 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
Candlewood Suites West Springfield by IHG
Exterior
Candlewood Suites West Springfield by IHG
2.5 star property
8.4 out of 10, Very Good, (771)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
The price is ₩139,796
₩159,997 total
includes taxes & fees
Oct 26 - Oct 27
Candlewood Suites West Springfield 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, (1286)
"Affordable and easy access to the Big E. Friendly staff. "
The price is ₩162,477
₩184,330 total
includes taxes & fees
Nov 9 - Nov 10
La Quinta Inn & Suites by Wyndham Springfield MA
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (551)
"Excellent location, friendly service, clean, comfortable room."
The price is ₩106,987
₩119,512 total
includes taxes & fees
Oct 15 - Oct 16
Travelodge by Wyndham Great Barrington Berkshires
Quality Inn West Springfield
Check-in/check-out kiosk
Quality Inn West Springfield
2.5 star property
7.0 out of 10, Good, (1014)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
The price is ₩120,039
₩137,384 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn West Springfield
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, (674)
"Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. "
The price is ₩147,214
₩164,432 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Blue – A Modern Hotel, an Ascend Collection Hotel
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (38)
"Nice hotel"
The price is ₩180,665
₩206,771 total
includes taxes & fees
Oct 26 - Oct 27
Blue – A Modern Hotel, an Ascend Collection Hotel
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (636)
"Easy check in"
The price is ₩89,427
₩99,889 total
includes taxes & fees
Nov 2 - Nov 3
Econo Lodge Lee - Great Barrington
D. Hotel Suites & Spa
Indoor pool
D. Hotel Suites & Spa
3.0 star property
9.4 out of 10, Exceptional, (2238)
"The staff is wonderful both at the hotel and dining ! "
The price is ₩156,766
₩182,111 total
includes taxes & fees
Oct 22 - Oct 23
D. Hotel Suites & Spa
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, (743)
"The property is very nice and the staff was extremely friendly and helpful."
The price is ₩203,988
₩227,855 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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 during your trip to Chester. Wander the lakeside and forest in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping, and theater 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

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Clean room, friendly staff, good breakfast, lots of action and people in lobby. I didn’t like that there wasn’t a fan in the bathroom, making it hard to put makeup on after showering in a humid bathroom… in a humid state. "
Kyra 2-night trip
Posted 10 hours ago
Tru by Hilton Chicopee Springfield

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is ₩120,039 per night from Oct 26 to Oct 27
₩120,039
₩137,384 total
Oct 26 - Oct 27
includes taxes & fees
7/10 Good! (1,010 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 traveler data. Other good choices for your trip to the area are Red Roof Inn PLUS+ West Springfield and Berkshire Mountain Lodge. 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! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
For additional details about picking new dates or cancelling your trip to Chester, go to https://www.expedia.com/service/.
What's the best accommodation near Logan International Airport (BOS)?
Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.
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, theaters, and monuments. In Chester, there are 2 hotels and other accommodations to choose from. Find out more about Chester.
What should I see while I'm in Chester?
A favorite place to visit is Chester Town Hall. You'll also find Glendale Falls and Pyramid Lake in the area. Check out what more to see and do in Expedia's Chester guide.
What's the seasonal weather like in Chester?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

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