Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from ₩86,236

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May 15 - May 16
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May 16 - May 17
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May 17 - May 19
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May 24 - May 26

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Compare 767 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1002)
"My Family and I had a really great time. The staff were accommodating. The ambience was natural and peaceful. The air fresh and clean...and the lake, totally awesome. The building front is not as impressive but once you get inside, it is a completely immersive experience. The restaurant experience was splendid. Wasn't sure whether i would like it, but boy did I. :) will definitely return. "
The price is ₩138,479
per night
May 21 - May 22
The Black Swan Lee - Lenox, Ascend Hotel Collection
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (882)
"Stay was great"
The price is ₩187,204
per night
May 27 - May 28
The Red Lion Inn
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (467)
"We liked that the property was almost totally self contained. i.e. indoor & outdoor activities, bar, snacks, etc."
The price is ₩190,298
per night
May 20 - May 21
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
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Terrace/patio
Seven Hills Inn
4.0 star property
7.8 out of 10, Good, (467)
"Great breakfast, amazing property, comfortable beds! Water in shower wasn’t hot, had to take a “warm-cold” fast shower but it didn’t matter. The view, the quiet, nature and siting areas made the stay perfect. Will come again!!"
Seven Hills Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (152)
"The Lakehouse Inn is really cute, right on a lake with wonderful waterfront spaces. The bathroom situation is more European--toilet and shower in the bathroom, sink outside. There was no tub, not a problem for me but good to be aware of. The morning breakfast was delicious! I was greeted with a white wine sangria. It's conveniently located for roaming around Stockbridge, Great Barrington, etc. Close to the Norman Rockwell museum, Hancock Shaker Village, Edith Wharton estate. Would absolutely...
The price is ₩184,822
per night
May 16 - May 17
Lakehouse Inn
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (647)
"Staff was very friendly. Facilities were clean and comfortable. Breakfast was quite good. Convenient location. We had a terrific stay!"
The price is ₩208,096
per night
May 27 - May 28
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Porch
The Cornell Inn, Lenox
3.0 star property
8.6 out of 10, Excellent, (1000)
"It was a great place to stay for the night. "
The price is ₩167,024
per night
May 16 - May 17
The Cornell Inn, Lenox
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (593)
"Great stay for one night. "
The price is ₩90,464
per night
May 20 - May 21
Monument Mountain Motel
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very Good, (212)
"Absolutely gorgeous room. Wonderful staff, I felt like royalty. "
The price is ₩169,310
per night
May 23 - May 24
Apple Tree Inn
Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk
Quality Inn
2.5 star property
8.0 out of 10, Very Good, (1000)
"Whenever we are in the area we have stayed and been pleased. "
The price is ₩109,660
per night
May 16 - May 17
Quality Inn
Standard Room | Premium bedding, pillowtop beds, in-room safe, desk
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (497)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is ₩191,557
per night
Jun 4 - Jun 5
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is ₩327,475
per night
May 28 - May 29
Chambery Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (26)
"Lucas was very accommodating and helpful. Pleasant and great place to stay. Great fresh breakfast!!"
The price is ₩248,483
per night
May 20 - May 21
Blackberry River Inn
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, (455)
"Manager was friendly and patient late at night. "
The price is ₩94,464
per night
May 19 - May 20
Travelodge by Wyndham Great Barrington Berkshires
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, (384)
"We loved this place. It's dog friendly, the place is clean and quiet. The proprietor is awesome. It's super friendly. We spent a total of 9 days here, and I'd definitely come back again. Thanks for a great stay"
The price is ₩150,596
per night
May 16 - May 17
The Briarcliff Motel
Property grounds
The Ponds at Foxhollow by Capital Vacations
3.0 star property
8.6 out of 10, Excellent, (110)
"Comfortable condo accommodations. Ample size, Workable kitchen. Comfortable bed. Lovely setting. And a community facility with a pool, workout equipment, and sauna too! Small but tangible complaint: outside lighting is very bright and shines into BR window. "
The Ponds at Foxhollow by Capital Vacations
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (382)
"This is a lovely place to say. Very warm and welcoming. The staff was very helpful and even brought a little doggy basket for my dog. It included a blanket, dog bowls treats and more!! Had a very very nice time. "
The price is ₩187,594
per night
May 16 - May 17
Shaker Mill Inn
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.2 out of 10, (504)
"The woman at check-in was kind. We had a lovely view. Place was in a great location with a comfortable bed."
The price is ₩86,236
per night
May 19 - May 20
Econo Lodge Lee - Great Barrington
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (321)
"Great B&B … everything is easy, clean, friendly owners, great breakfast! "
The price is ₩142,838
per night
May 25 - May 26
Locust Tree Bed and Breakfast LLC
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (200)
"Nicely located to Lenox. Friendly greeting and very pleasant overreview of property. I was Upgraded to King room with no charge as hotel wasn't full. Large spacious period decor, with large soaking tub in generous barhriom. Sound travels through hallways, guest rooms and rooms above, as bedroom has areas rugs on hard wood floors. If you are a light sleeper, ask for top floor. "
The price is ₩122,366
per night
May 16 - May 17
The Lenox Collection
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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.

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St, West Springfield, MA
The price is ₩116,369 per night from May 22 to May 23
₩116,369
per night
May 22 - May 23
7.2/10 Good! (1,000 reviews)

Stay near popular Chester attractions

Image for Chester Town Hall

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
Chester Town Hall

Chester hotels information

Number of reviews
5,884
Accommodation
767 hotels
Lowest Price
₩86,236
Highest Price
₩327,475

Frequently asked questions

What's the best place to stay in Chester?

D. Hotel Suites & Spa, located 19.1 mi (30.7 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 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! 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 are some hotels with pools in Chester?

La Quinta Inn & Suites by Wyndham Springfield MA: 3-star hotel located near Springfield Museums. Offers a children's pool, an indoor pool, and a snack bar. Tru by Hilton Chicopee Springfield and D. Hotel Suites & Spa are two additional hotels that feature an onsite pool. View all hotels with pools in Chester.

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 Jacob's Pillow and Otis Reservoir 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.