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Top Chester hotels

D. Hotel Suites & Spa
The hotel was great. The biggest thing keeping this from being excellent was that the thermostat in the room didn't work. The fan was set to auto yet the heater kept heating until it was too hot. We had to turn it off at times and it made sleeping uncomfortably hot.
Reviewed on Nov 29, 2025

Berkshire Mountain Lodge
Everything was perfect!!!! Check in quick, staff so helpful. Room perfect!
Reviewed on Nov 24, 2025

Berkshires Untold
Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere.
Reviewed on Nov 10, 2025

Courtyard by Marriott West Springfield
The room was great. The staff quick and
Reviewed on Nov 27, 2025

The Ellery
beautifully renovated, excellent staff, quiet, great breakfast
Reviewed on Nov 26, 2025

The Red Lion Inn
Quaint Inn located in the Berkshire. Dinner in the tavern was delish. The main inn lobby has plenty of seating to lounge around and people watch. We enjoyed our stay.
Reviewed on Nov 20, 2025

Tru by Hilton Chicopee Springfield
Courteous staff clean rooms
Reviewed on Nov 23, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
Very sweet staff mf accommodating
Reviewed on Nov 24, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Staff very helpful
Reviewed on Nov 24, 2025
Chester Hotel & Travel Guide\n
You may have noticed there aren't any Travelocity-featured rooms in Chester. Travelers hoping to make memories in Chester should make reservations in one of the 15 hotels within easy driving distance.
The nearest Travelocity-listed room is the Holiday Inn Express & Suites Westfield, Massachusetts, situated 16 miles (25 kilometers) from the urban core of Chester. For an alternative, how about you try the Sunset Inn, located in Massachusetts, which is 14 miles (22 kilometers) from the heart of the city.
14 miles (22 kilometers) from the main part of Chester, you will find the Pilgrim Inn. The Econo Lodge can be found approximately 17 miles (28 kilometers) away. The Super 8 Lee/Berkshires/Outlet Area and also the Quality Inn Westfield - Springfield are some other Travelocity-listed accommodation options worth checking out around Chester.
When you've got the time, adventurous travelers could explore the other cultural and scenic delights of Western Massachusetts. Western Massachusetts is well known for mountains, and common tourist places of interest are history museums. Popular activities in this part of United States of America include skiing.
Looking for things to do? Spend some time exploring Volleyball Hall of Fame and Mount Tom, which you'll find in Holyoke, 18 miles (28 kilometers) east of Chester. The Homewood Suites by Hilton Holyoke-Springfield/North and Howard Johnson Holyoke/Springfield are just some examples of the great short and long-stay options in Holyoke. For another option, stay in Hadley, 20 miles (34 kilometers) east of Chester, where you can choose from the Courtyard by Marriott Hadley Amherst and Old Mill Inn. The Hadley Farm Museum and Porter Phelps Huntington Museum are some of the more frequented attractions to explore when visiting Hadley.
Before you head home, consider spending a few hours enjoying thrills and spills with excited lovers of sports at a local match. Times Union Center is located 45 miles (76 kilometers) to the northwest of Chester. Wise travelers wishing to book a Travelocity-listed hotel nearby can choose from the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.
Bradley International Airport is a convenient airport, and can be found 30 miles (46 kilometers) outside central Chester. Conveniently located hotel options include Sheraton Hartford Hotel at Bradley Airport and Holiday Inn Express & Suites Bradley Airport.
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D. Hotel Suites & Spa
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