Photo by Elizabeth Massa Peroulakis

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Aug 29 - Aug 30
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Aug 30 - Aug 31
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Aug 29 - Aug 31
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Sep 5 - Sep 7

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Compare 826 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Chester hotels

River Valley Inn
Basic Studio, 1 King Bed | 1 bedroom, desk, laptop workspace, free WiFi

River Valley Inn

2.0 star property
8.8 out of 10, Excellent, (42)
"Great quiet motel. "
The price is ₩178,584
₩199,478 total
includes taxes & fees
Aug 31 - Sep 1
River Valley Inn
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, (1003)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ₩175,330
₩195,843 total
includes taxes & fees
Sep 7 - Sep 8
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (546)
"Excellent location, friendly service, clean, comfortable room."
The price is ₩103,828
₩115,983 total
includes taxes & fees
Sep 8 - Sep 9
Travelodge by Wyndham Great Barrington Berkshires
D. Hotel Suites & Spa
Indoor pool

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2228)
"Nice hotel a bunch of options and the restaurant is delicious."
The price is ₩170,141
₩197,662 total
includes taxes & fees
Sep 3 - Sep 4
D. Hotel Suites & Spa
Fairfield Inn & Suites Springfield Holyoke
Property amenity

Fairfield Inn & Suites Springfield Holyoke

2.5 star property
9.2 out of 10, Wonderful, (563)
"Nice hotel"
The price is ₩168,893
₩188,654 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites Springfield Holyoke
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1004)
"Very clean rooms and excellent staff."
The price is ₩147,075
₩164,283 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is ₩109,365
₩122,157 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Lenox
Element Lenox Berkshires
Lobby lounge

Element Lenox Berkshires

3.0 star property
9.6 out of 10, Exceptional, (4)
"New hotel very nice"
The price is ₩210,424
₩235,043 total
includes taxes & fees
Sep 7 - Sep 8
Element Lenox Berkshires
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (744)
"A great mom & pop motel. Clean and friendly "
The price is ₩106,527
₩119,000 total
includes taxes & fees
Sep 1 - Sep 2
Monument Mountain Motel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (599)
"Amazing place to stay. Can’t wait to go again. "
The price is ₩106,257
₩149,616 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
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, (1002)
"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 ₩176,756
₩251,559 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
Blue - A Modern Hotel, Ascend Hotel Collection
Coffee service

Blue - A Modern Hotel, Ascend Hotel Collection

2.5 star property
The price is ₩175,330
₩200,665 total
includes taxes & fees
Sep 28 - Sep 29
Blue - A Modern Hotel, Ascend Hotel Collection
Hampton Inn Hadley-Amherst Area
Exterior

Hampton Inn Hadley-Amherst Area

2.5 star property
9.0 out of 10, Wonderful, (931)
"Friendly staff."
The price is ₩189,299
₩211,447 total
includes taxes & fees
Sep 21 - Sep 22
Hampton Inn Hadley-Amherst Area
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (699)
"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 ₩222,386
₩248,405 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Great staff! Comfortable bed! "
The price is ₩198,865
₩222,131 total
includes taxes & fees
Sep 4 - Sep 5
Hampton Inn & Suites Berkshires-Lenox
Tru by Hilton Chicopee Springfield
Lobby

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1012)
"Great housekeepers; available pool & gym; free parking & breakfast!"
The price is ₩175,330
₩198,911 total
includes taxes & fees
Sep 7 - Sep 8
Tru by Hilton Chicopee Springfield
Fairfield Inn & Suites Springfield Northampton/Amherst
Lobby

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
9.2 out of 10, Wonderful, (977)
"The place is amazing "
The price is ₩210,424
₩235,043 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites Springfield Northampton/Amherst
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (27)
"Do hotel, very clean we had a great day"
The price is ₩195,958
₩218,885 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (572)
"Fabulous place"
The price is ₩210,424
₩235,043 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (760)
"Quite and good location to around towns"
The price is ₩220,115
₩245,868 total
includes taxes & fees
Sep 28 - Sep 29
Hotel On North
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 riverfront 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

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 ₩135,807 per night from Sep 7 to Sep 8
₩135,807
₩155,431 total
Sep 7 - Sep 8
includes taxes & fees
7/10 Good! (1,004 reviews)

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 traveler data. Other good choices for your trip to the area are Quality Inn West Springfield and La Quinta Inn & Suites by Wyndham Springfield MA. 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.