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Chester Hotels

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May 5 - May 6
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May 6 - May 7
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May 10 - May 12

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Top 10 trending Chester hotels

Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Our room was on the lake and had a nice deck where we could relax with a beer purchased (very cheap!) from the front reception area. Also the Indian restaurant was excellent with ample portions. And because it's in MA, everything was ADA accessible which made it feel inclusive to all. Some guest had their dogs with them but the place was very clean even with pets. "
The price is P 6,144
per night
May 7 - May 8
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, (874)
"Nice renovated and updated room in the maple glen building. "
The price is P 6,090
per night
May 6 - May 7
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, (461)
"The room was spacious- 2 bedrooms, large living room, full kitchen, terrace, TV's in every room. It was spotless when we arrived. The stay was exceptional."
The price is P 7,974
per night
May 6 - May 7
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, (150)
"Love this Inn, all employees were friendly and knowledgeable about things to do in the area. The breakfast was delicious . I look forward to staying at the Inn again."
The price is P 7,745
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, (645)
"Employees were excellent. Very nice location to stay. Pool was nice and well kept "
The price is P 9,237
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)
"Great breakfast. "
The price is P 6,887
per night
May 7 - May 8
The Cornell Inn, Lenox
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (588)
"The owners are what make this property very good. Very clean"
The price is P 3,815
per night
May 6 - May 7
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 P 6,456
per night
May 16 - May 17
Apple Tree Inn
1 bedroom, premium bedding, pillowtop beds, desk
Quality Inn
2.5 star property
8.0 out of 10, Very Good, (1001)
"Generally a good stay, great value"
The price is P 4,595
per night
May 8 - May 9
Quality Inn
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, (496)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is P 8,532
per night
May 19 - May 20
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 P 13,723
per night
May 13 - May 14
Chambery Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (24)
"Lucas was very accommodating and helpful. Pleasant and great place to stay. Great fresh breakfast!!"
The price is P 10,413
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, (454)
" price, close to everything, "
The price is P 3,959
per night
May 6 - May 7
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 P 5,743
per night
May 13 - May 14
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, (380)
"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 P 7,515
per night
May 8 - May 9
Shaker Mill Inn
Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (502)
"Not the greatest place in the world, but well worth the bang for my buck. Would recommend if you are staying on a budget, but do not have high expectations."
The price is P 3,614
per night
May 6 - May 7
Econo Lodge Lee - Great Barrington
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (319)
"The friendly owner and easy nature was a pleasure. Breakfast was perfectly prepared. I really enjoyed staying there. "
The price is P 6,024
per night
May 6 - May 7
Locust Tree Bed and Breakfast LLC
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (189)
"Nice renovation of an older property - still thin walls, not a lot of hot water, and minimal gym "
The price is P 4,657
per night
May 12 - May 13
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 P4,898 per night from May 20 to May 21
P4,898
per night
20 May - 21 May
7.2/10 Good! (1,004 reviews)

Near an Attraction

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
5,891
Accommodation
769 hotels
Lowest Price
P3,614
Highest Price
P13,723

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.

Recent Reviews in Chester
Expedia verified reviews

The Red Lion Inn

The Red Lion Inn

5/5 Excellent
"Nice renovated and updated room in the maple glen building. "
A verified traveler from Norwich stayed at The Red Lion Inn
Posted 3 hours ago
The Red Lion Inn