Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from ￥10,507

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 16 - Jul 17
Tomorrow
Jul 17 - Jul 18
This weekend
Jul 18 - Jul 20
Next weekend
Jul 25 - Jul 27

Filter by

Guest rating
Guest rating
Star rating

Compare 827 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

D. Hotel Suites & Spa
Swimmers can enjoy the pool surrounded by a checkered tile floor and high ceilings.

D. Hotel Suites & Spa

3.0 star property
9.4 out of 10, Exceptional, (2279)
"Great hospitality and very pretty hotel and grounds"
The price is ￥20,237
￥23,511 total
includes taxes & fees
Jul 29 - Jul 30
D. Hotel Suites & Spa
Hotel On North
Enjoy a diverse menu at this restaurant, featuring a selection of drinks and a modern design.

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is ￥28,142
￥31,434 total
includes taxes & fees
Jul 28 - Jul 29
Hotel On North
Berkshire Mountain Lodge
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and gas range.

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (514)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
Berkshire Mountain Lodge
Hampton Terrace Inn
Welcome to this charming two-story house with a cozy front porch and balcony, featuring a wreath above the door and green shutters.

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 ￥51,860
￥57,927 total
includes taxes & fees
Jul 20 - Jul 21
Hampton Terrace Inn
Hampton Inn Westfield
Two beds with white linens and headboards feature a unique design, complemented by a desk and chair.

Hampton Inn Westfield

2.5 star property
8.4 out of 10, Very Good, (750)
"It was clean & quiet. The breakfast buffet was very much appreciated "
The price is ￥20,124
￥22,478 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn Westfield
Gedney Farm
Enjoy a serene dining experience in a picturesque countryside setting at Gedney Farm.

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (121)
"Beautiful, clean property that is well run."
Gedney Farm
TownePlace Suites by Marriott Hadley Amherst
Relax in the hotel's spacious lobby, featuring a central seating area with sofas and armchairs, a coffee table, and a large abstract artwork.

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 ￥26,531
￥29,635 total
includes taxes & fees
Aug 3 - Aug 4
TownePlace Suites by Marriott Hadley Amherst
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

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 ￥64,414
￥77,922 total
includes taxes & fees
Jul 22 - Jul 23
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Daniel Stebbins House
A charming two-story home with a green door and picket fence, surrounded by a beautifully manicured lawn and flowering bushes.

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 ￥39,940
￥44,613 total
includes taxes & fees
Jul 20 - Jul 21
Daniel Stebbins House
The Constance by the Lenox Collection
Situated in a tranquil setting, The Whittock offers a traditional home with a covered front porch and mature trees surrounding the property.

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (494)
"Had a fantastic stay, love this property. Cant wsit to go back"
The price is ￥25,641
￥28,641 total
includes taxes & fees
Jul 22 - Jul 23
The Constance by the Lenox Collection
The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

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 ￥28,892
￥38,926 total
includes taxes & fees
Aug 13 - Aug 14
The Red Lion Inn
La Quinta Inn & Suites by Wyndham Springfield MA
Relax by the pool surrounded by comfortable lounge chairs and a serene atmosphere.

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
8.2 out of 10, Very Good, (1266)
"Staff were amazing."
The price is ￥16,835
￥19,098 total
includes taxes & fees
Aug 12 - Aug 13
La Quinta Inn & Suites by Wyndham Springfield MA
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

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
Traditional hotel with a welcoming entrance, flanked by lush greenery and a flag.

Residence Inn by Marriott West Springfield

3.0 star property
8.6 out of 10, Excellent, (445)
"Great stay"
The price is ￥19,953
￥22,836 total
includes taxes & fees
Jul 27 - Jul 28
Residence Inn by Marriott West Springfield
Naomi's Inn Bed & Breakfast
Classic bedroom with a large bed, nightstands, and elegant curtains.

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (399)
"Very unique property! Comfortable and spacious rooms, and nice breakfast area."
The price is ￥16,700
￥18,946 total
includes taxes & fees
Jul 31 - Aug 1
Naomi's Inn Bed & Breakfast
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

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
Guests can enjoy a serene outdoor setting with a tranquil lawn and a charming two-story building in the background.

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (512)
"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 ￥23,646
￥26,412 total
includes taxes & fees
Jul 21 - Jul 22
The Little Lion
Old Mill Inn
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, white cabinetry, and a tiled backsplash.

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 ￥69,992
￥78,182 total
includes taxes & fees
Jul 19 - Jul 20
Old Mill Inn
Candlewood Suites West Springfield by IHG
Stylish hotel exterior with a central entrance and evenly spaced windows.

Candlewood Suites West Springfield by IHG

2.5 star property
8.4 out of 10, Very Good, (731)
"A bit older facilities but otherwise meets all the basic needs and is easy on and off the 91 highway "
The price is ￥12,388
￥14,178 total
includes taxes & fees
Jul 27 - Jul 28
Candlewood Suites West Springfield by IHG
Hampton Inn & Suites Berkshires-Lenox
Hotel features a two-story design with a flat roof and a mix of brick and siding.

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Good lodgings in a great area to visit."
The price is ￥22,655
￥25,305 total
includes taxes & fees
Jul 30 - Jul 31
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Chester

Experience the hiking, camping, and waterfalls in Chester!

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

Top Chester Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Booked this hotel for our wedding weekend and it did not disappoint! The staff was AMAZING!! The property we’ll maintained and everyone genuinely made our stay that much better !!"
Tameika 1-night trip
Posted 1 day ago
D. Hotel Suites & Spa

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 traveler data. Other good choices for your trip to the area are D. Hotel Suites & Spa and Quality Inn West Springfield. See all available top hotels, or vacation rentals in Chester.

What are some of the best vacation rentals in Chester?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This vacation home rental outside of Chester offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. See all 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.