Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from ฿2,238

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Check prices for these dates

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13 Jul - 14 Jul
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14 Jul - 15 Jul
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18 Jul - 20 Jul
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25 Jul - 27 Jul

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Top 10 Chester hotels and places to stay

D. Hotel Suites & Spa
Indoor pool

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2270)
"Great hospitality and very pretty hotel and grounds"
The price is ฿3,565
฿4,142 total
includes taxes & fees
27 Jul - 28 Jul
D. Hotel Suites & Spa
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is ฿6,131
฿6,849 total
includes taxes & fees
24 Jul - 25 Jul
Hotel On North
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (513)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
Berkshire Mountain Lodge
Hampton Terrace Inn
Exterior

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is ฿11,384
฿12,715 total
includes taxes & fees
16 Jul - 17 Jul
Hampton Terrace Inn
Hampton Inn Westfield
Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout curtains

Hampton Inn Westfield

2.5 star property
8.4 out of 10, Very good, (748)
"It was clean & quiet. The breakfast buffet was very much appreciated "
The price is ฿4,384
฿4,897 total
includes taxes & fees
20 Jul - 21 Jul
Hampton Inn Westfield
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (120)
"Great staff. Quiet.. and an excellent chef! Unique property and well worth it!"
Gedney Farm
TownePlace Suites by Marriott Hadley Amherst
Lobby

TownePlace Suites by Marriott Hadley Amherst

3.0 star property
9.6 out of 10, Exceptional, (33)
"It was a beautiful property."
The price is ฿6,252
฿6,984 total
includes taxes & fees
12 Aug - 13 Aug
TownePlace Suites by Marriott Hadley Amherst
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is ฿14,139
฿17,105 total
includes taxes & fees
15 Jul - 16 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Daniel Stebbins House
Exterior

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (45)
"Beautiful home that provided a relaxed, comfortable stay. If we are in the area again we would definitely return."
The price is ฿8,767
฿9,793 total
includes taxes & fees
15 Jul - 16 Jul
Daniel Stebbins House
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (492)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is ฿5,507
฿6,151 total
includes taxes & fees
15 Jul - 16 Jul
The Constance by the Lenox Collection
The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"I had excellent stay at the Red Lion Inn "
The price is ฿6,131
฿8,298 total
includes taxes & fees
15 Jul - 16 Jul
The Red Lion Inn
La Quinta Inn & Suites by Wyndham Springfield MA
Indoor pool

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
8.2 out of 10, Very good, (1269)
"Staff were amazing."
The price is ฿3,695
฿4,192 total
includes taxes & fees
17 Jul - 18 Jul
La Quinta Inn & Suites by Wyndham Springfield MA
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Residence Inn by Marriott West Springfield
Exterior

Residence Inn by Marriott West Springfield

3.0 star property
8.6 out of 10, Excellent, (444)
"Great stay"
The price is ฿4,347
฿4,975 total
includes taxes & fees
27 Jul - 28 Jul
Residence Inn by Marriott West Springfield
Naomi's Inn Bed & Breakfast
Room (Louis XIV) | 2 bedrooms, individually decorated, individually furnished

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (398)
"Very unique property! Comfortable and spacious rooms, and nice breakfast area."
The price is ฿3,666
฿4,159 total
includes taxes & fees
15 Jul - 16 Jul
Naomi's Inn Bed & Breakfast
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Little Lion
Pet-friendly

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (511)
"Hotel was clean and facilities were maintained. Best part was that you are permitted to use amenities at The Red Lion Inn down the road. "
The price is ฿5,191
฿5,798 total
includes taxes & fees
15 Jul - 16 Jul
The Little Lion
Old Mill Inn
Room, River View (The Williamsburg Suite) | Private kitchen | Coffee/tea maker, cleaning supplies, paper towels

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (486)
"Quiet and very relaxing, making it a great and enjoyable stay! "
The price is ฿15,364
฿17,161 total
includes taxes & fees
19 Jul - 20 Jul
Old Mill Inn
Candlewood Suites West Springfield by IHG
Exterior

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very good, (730)
"A bit older facilities but otherwise meets all the basic needs and is easy on and off the 91 highway "
The price is ฿2,569
฿2,941 total
includes taxes & fees
3 Aug - 4 Aug
Candlewood Suites West Springfield by IHG
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Good lodgings in a great area to visit."
The price is ฿4,806
฿5,368 total
includes taxes & fees
31 Jul - 1 Aug
Hampton Inn & Suites Berkshires-Lenox
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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Learn more about Chester

Experience the hiking, camping and waterfalls in Chester!

See all hotels in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Frequently asked questions

What's the best place to stay in Chester?

La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 km) from the heart of Chester, is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are D. Hotel Suites & Spa and Quality Inn 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, the majority of room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

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 offer an on-site pool. View all hotels with pools in Chester.

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, theatres and monuments. In Chester, there are 2 hotels and other accommodation options to choose from. Find out more about Chester.

What is there to see in Chester?

A favourite place to visit is Chester Town Hall. You'll also find Glendale Falls and Pyramid Lake in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.