Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from NT$2,127

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Compare 836 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Had a wonderful time "
The price is NT$3,799
NT$4,244 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Wonderful place to stay"
The price is NT$4,023
NT$4,494 total
includes taxes & fees
Sep 8 - Sep 9
The Yankee, Trademark Collection by Wyndham

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (671)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is NT$4,819
NT$5,383 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (516)
"Great place , love it, will return"
The price is NT$4,551
NT$5,083 total
includes taxes & fees
Sep 10 - Sep 11
The Constance by the Lenox Collection

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1000)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is NT$3,830
NT$5,451 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (622)
"It was lovely!"
The price is NT$1,912
NT$2,136 total
includes taxes & fees
Aug 26 - Aug 27
Econo Lodge Lee - Great Barrington

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is NT$5,924
NT$7,953 total
includes taxes & fees
Aug 18 - Aug 19
The Red Lion Inn

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.4 out of 10, Good, (537)
"Excellent location, friendly service, clean, comfortable room."
The price is NT$2,250
NT$2,513 total
includes taxes & fees
Sep 1 - Sep 2
Travelodge by Wyndham Great Barrington Berkshires

Quality Inn West Springfield

2.5 star property
7.0 out of 10, Good, (1006)
"My daughter and the kids said it was perfect for their overnight stay after visiting Six Flags. "
The price is NT$2,779
NT$3,181 total
includes taxes & fees
Aug 26 - Aug 27
Quality Inn West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 star property
7.0 out of 10, Good, (1000)
"Rooms were clean and the staff was nice. "
The price is NT$2,665
NT$3,050 total
includes taxes & fees
Aug 21 - Aug 22
Red Roof Inn PLUS+ West Springfield

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (690)
"This was our third year of two summer weeks at Oak 'n' Spruce. The accommodations are comfortable and convenient, and the staff is wonderful. We hope to be back next summer."
The price is NT$2,745
NT$3,485 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

FairBridge Inn Express

2.5 star property
5.4 out of 10, (766)
"Close to our target event a plus"
The price is NT$2,127
NT$2,376 total
includes taxes & fees
Aug 26 - Aug 27
FairBridge Inn Express

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very Good, (742)
"I would definitely stay here again!"
The price is NT$2,940
NT$3,365 total
includes taxes & fees
Aug 24 - Aug 25
Candlewood Suites West Springfield by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (856)
"Consistently a clean room with welcoming staff."
The price is NT$3,450
NT$3,854 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (557)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
8.2 out of 10, Very Good, (1268)
"Place is clean"
The price is NT$3,442
NT$3,905 total
includes taxes & fees
Aug 21 - Aug 22
La Quinta Inn & Suites by Wyndham Springfield MA

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (724)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is NT$4,996
NT$5,581 total
includes taxes & fees
Aug 25 - Aug 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2234)
"always a good stay"
The price is NT$3,871
NT$4,498 total
includes taxes & fees
Aug 19 - Aug 20
D. Hotel Suites & Spa

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (648)
"Great place to stay. Excellent staff."
The price is NT$3,720
NT$4,155 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Fairfield Inn & Suites Springfield Northampton/Amherst

3.0 star property
9.2 out of 10, Wonderful, (975)
"The place is amazing "
The price is NT$4,560
NT$5,093 total
includes taxes & fees
Aug 17 - Aug 18
Fairfield Inn & Suites Springfield Northampton/Amherst
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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Stay near popular Chester attractions

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.

Learn more about Chester

Experience the hiking, camping, and riverfront in Chester!

Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

Frequently asked questions

What's the best place to stay in Chester?

Quality Inn West Springfield, located 20.6 mi (33.1 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 Berkshire Mountain Lodge 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 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 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.