Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from NT$2,122

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

The Ellery

3.5 star property
9.2 out of 10, Wonderful, (784)
"Wonderful breakfast and cute and cozy lobby "
The price is NT$4,012
NT$4,481 total
includes taxes & fees
Aug 18 - Aug 19
The Ellery

River Valley Inn

2.0 star property
8.6 out of 10, Excellent, (37)
"Great quiet motel. "
The price is NT$3,850
NT$4,300 total
includes taxes & fees
Aug 13 - Aug 14
River Valley Inn

Element Lenox Berkshires

3.0 star property
10.0 out of 10, Exceptional, (2)
The price is NT$4,547
NT$5,079 total
includes taxes & fees
Sep 1 - Sep 2
Element Lenox Berkshires

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2232)
"Clean, comfortable beds and fun live music at the restaurant attached"
The price is NT$3,862
NT$4,486 total
includes taxes & fees
Aug 19 - Aug 20
D. Hotel Suites & Spa

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (406)
"We had a great stay and breakfast was delicious!"
The price is NT$3,381
NT$3,835 total
includes taxes & fees
Aug 17 - Aug 18
Naomi's Inn Bed & Breakfast

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$2,244
NT$2,506 total
includes taxes & fees
Sep 1 - Sep 2
Travelodge by Wyndham Great Barrington Berkshires

Fairfield Inn & Suites Springfield Holyoke

2.5 star property
9.2 out of 10, Wonderful, (552)
"Great place in a great location."
The price is NT$3,530
NT$3,943 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites Springfield Holyoke

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (555)
"Amazing place to stay. Can’t wait to go again. "
Berkshire Mountain Lodge

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (736)
"Helpful, friendly staff. Clean, convenient, quiet."
Monument Mountain Motel

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Had a wonderful time "
The price is NT$3,789
NT$4,232 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (782)
"My stay was perfect. I can't wait to stay there again. "
The price is NT$2,363
NT$2,640 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Lenox

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1004)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is NT$3,820
NT$5,436 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires

Tru by Hilton Chicopee Springfield

2.5 star property
8.8 out of 10, Excellent, (1005)
"Staff is wonderful & attentive. "
The price is NT$3,280
NT$3,722 total
includes taxes & fees
Aug 24 - Aug 25
Tru by Hilton Chicopee Springfield

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$4,536
NT$5,067 total
includes taxes & fees
Aug 18 - Aug 19
Fairfield Inn & Suites Springfield Northampton/Amherst

Best Western Springfield West Inn

2.5 star property
7.8 out of 10, Good, (1009)
"Great stay"
The price is NT$2,797
NT$3,201 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Springfield West Inn

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (569)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is NT$4,547
NT$5,079 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires

Hampton Inn Hadley-Amherst Area

2.5 star property
9.0 out of 10, Wonderful, (923)
"Front desk was very nice and helpful. Kitchen and cleaning staff were great as well."
The price is NT$4,043
NT$4,516 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn Hadley-Amherst Area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1008)
"Very clean rooms and excellent staff."
The price is NT$3,560
NT$3,976 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (670)
"Fun place and very clean. Friendly staff and an amazing outdoor area to hang out."
The price is NT$4,794
NT$5,355 total
includes taxes & fees
Sep 1 - Sep 2
Berkshires Untold

Hotel Northampton

3.5 star property
9.2 out of 10, Wonderful, (1006)
"Historic hotel but was in great condition and very beautiful."
Hotel Northampton
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.