Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from ¥10,568

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Compare 838 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1008)
"Great Indian restaurant in the hotel!"
The price is ¥16,034
¥17,910 total
includes taxes & fees
Nov 2 - Nov 3
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (763)
"We had a nice room and the food was delicious. Great place to stay. "
The price is ¥13,205
¥14,749 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1010)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
The price is ¥20,237
¥22,605 total
includes taxes & fees
Nov 2 - Nov 3
The Yankee, Trademark Collection by Wyndham
Red Roof Inn PLUS+ West Springfield
2.5 star property
7.0 out of 10, Good, (1013)
"The staff was very helpful and nice"
The price is ¥14,803
¥16,943 total
includes taxes & fees
Nov 2 - Nov 3
Red Roof Inn PLUS+ West Springfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (902)
"Excellent customer service and great rooms"
The price is ¥15,544
¥17,362 total
includes taxes & fees
Nov 7 - Nov 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1006)
"Very friendly staff. "
The price is ¥19,268
¥27,423 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
River Valley Inn
2.0 star property
8.6 out of 10, Excellent, (78)
"Great quiet motel. "
The price is ¥17,958
¥20,059 total
includes taxes & fees
Nov 16 - Nov 17
River Valley Inn
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 ¥17,988
¥20,092 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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 ¥17,023
¥19,015 total
includes taxes & fees
Nov 11 - Nov 12
Hotel On North
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (552)
"Excellent location, friendly service, clean, comfortable room."
The price is ¥11,318
¥12,643 total
includes taxes & fees
Oct 20 - Oct 21
Travelodge by Wyndham Great Barrington Berkshires
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1011)
"Picture perfect Inn"
The price is ¥20,584
¥29,774 total
includes taxes & fees
Nov 9 - Nov 10
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (757)
"Lovely spot, great accommodations, friendly staff, and great location."
The price is ¥17,520
¥21,678 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 ¥14,789
¥16,926 total
includes taxes & fees
Oct 26 - Oct 27
Candlewood Suites West Springfield by IHG
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (705)
"Great stay, perfect "
The price is ¥14,065
¥19,081 total
includes taxes & fees
Nov 2 - Nov 3
Berkshire Mountain Lodge
La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
8.2 out of 10, Very Good, (1291)
"Affordable and easy access to the Big E. Friendly staff. "
The price is ¥17,317
¥19,646 total
includes taxes & fees
Nov 11 - Nov 12
La Quinta Inn & Suites by Wyndham Springfield MA
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (675)
"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 ¥14,970
¥16,721 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Inn Express Hotel & Suites Great Barrington by IHG
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very Good, (552)
"Very quiet and comfortable "
The price is ¥14,620
¥16,330 total
includes taxes & fees
Nov 3 - Nov 4
The Constance by the Lenox Collection
Quality Inn West Springfield
2.5 star property
7.0 out of 10, Good, (1017)
"Convenient nice cozy hotel with breakfast included and spacious rooms. "
The price is ¥12,699
¥14,533 total
includes taxes & fees
Oct 29 - Oct 30
Quality Inn West Springfield
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (638)
"Stayed one night just because we had been driving for 10 hours but nice place for the price. "
The price is ¥9,461
¥10,568 total
includes taxes & fees
Nov 2 - Nov 3
Econo Lodge Lee - Great Barrington
Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
9.4 out of 10, Exceptional, (45)
"Nice hotel"
The price is ¥18,541
¥21,220 total
includes taxes & fees
Oct 29 - Oct 30
Blue – A Modern Hotel, an Ascend Collection Hotel
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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Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

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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.
What are some of the best vacation rentals in Chester?
Spacious 5-bedroom house in charming Lee with WiFi: This vacation home rental outside of Chester offers a fireplace, a barbecue grill, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a microwave can make your vacation run smoothly. See all 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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