Lodging Image

Find hotels in Chester, MA from ￥12,345

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jun 19 - Jun 21
In two weeks
Jun 26 - Jun 28

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chester hotels

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ￥17,818
￥19,903 total
includes taxes & fees
Jun 16 - Jun 17
The Yankee Inn
Standard Room, 2 Queen Beds, Non Smoking | Pillowtop beds, desk, laptop workspace, blackout drapes

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
7.8 out of 10, Good, (198 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is ￥15,256
￥17,459 total
includes taxes & fees
Jun 16 - Jun 17
Baldwin Inn & Suites, SureStay Collection by Best Western
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"Breakfast was reasonable. We had issue with our room and the staff helpfully moved us to another room. Would stay again"
United States
Anandaraja
The price is ￥18,460
￥20,619 total
includes taxes & fees
Jun 18 - Jun 19
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,006 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ￥21,656
￥24,190 total
includes taxes & fees
Jul 6 - Jul 7
Quality Inn Lee - Lenox South
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (565 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ￥14,101
￥15,751 total
includes taxes & fees
Jun 16 - Jun 17
The Little Lion
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (107 reviews)
"Most comfortable hotel bed I've ever slept in"
United States
Matthew
The price is ￥22,434
￥25,059 total
includes taxes & fees
Jun 22 - Jun 23
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,014 reviews)
"Very nice, clean, love the parking. Great hotel"
United States
Thomas Howard
The price is ￥23,876
￥26,670 total
includes taxes & fees
Jun 30 - Jul 1
The Ellery
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (868 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is ￥12,330
￥13,774 total
includes taxes & fees
Jun 18 - Jun 19
Monument Mountain Motel
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ￥11,537
￥12,655 total
includes taxes & fees
Jun 15 - Jun 16
Pleasant Valley Motel West Stockbridge
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (867 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ￥12,659
￥14,140 total
includes taxes & fees
Jun 15 - Jun 16
Howard Johnson by Wyndham Lenox
Studio Suite, Multiple Beds | Bathroom | Hair dryer, towels, soap, shampoo

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (165 reviews)
"It's a really nice place to stay!"
United States
Vidita
The price is ￥15,723
￥17,563 total
includes taxes & fees
Jun 22 - Jun 23
River Valley Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (986 reviews)
"Great lobby and dining room atmosphere!"
United States
Carin
The price is ￥22,720
￥25,378 total
includes taxes & fees
Jun 17 - Jun 18
Berkshires Untold
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (583 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is ￥12,659
￥14,140 total
includes taxes & fees
Jun 15 - Jun 16
Travelodge by Wyndham Great Barrington Berkshires
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (942 reviews)
"The coffee was fantastic. Rooms were quiet"
United States
Richard
The price is ￥15,841
￥17,695 total
includes taxes & fees
Jul 14 - Jul 15
Quality Inn Westfield - Springfield
Room (Louis XIV) | Individually decorated, individually furnished, iron/ironing board

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (442 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is ￥18,907
￥21,450 total
includes taxes & fees
Jun 15 - Jun 16
Naomi's Inn Bed & Breakfast
Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,210 reviews)
"Breakfast was excellent."
United States
Candyce
The price is ￥19,490
￥22,806 total
includes taxes & fees
Jun 21 - Jun 22
D. Hotel Suites & Spa
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect!!"
United States
Grzegorz
The price is ￥22,882
￥25,559 total
includes taxes & fees
Jun 15 - Jun 16
Berkshire Lake Lodge
Apartment (0 Bedroom) | Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is ￥15,704
￥43,268 total
includes taxes & fees
Jun 18 - Jun 19
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Exterior

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
West Springfield
7.8 out of 10, Good, (1,002 reviews)
"Good stay for the value"
United States
Frank
The price is ￥15,381
￥17,604 total
includes taxes & fees
Jun 17 - Jun 18
Best Western Springfield West Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (979 reviews)
"Very quiet and clean will book again"
United States
Sade
The price is ￥22,489
￥28,700 total
includes taxes & fees
Jul 14 - Jul 15
Berkshire Mountain Lodge
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Chester attractions

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.
See properties

Learn more about Chester

Experience the hiking, camping, and waterfalls in Chester!

See all hotels in Chester
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

8/10 Good
"Our room was clean and comfortable but we had several issues with the bathroom. Saturday morning we reported that the toilet seat was loose, the bathroom sink was not draining and that the shower doors would not stay shut. We were told it would be taken care of by the time we returned. The toilet seat was fastened but nothing else was addressed. No room service with fresh towels, coffee pod refills or tissues since there were only 2 in the box. I mentioned the remaining 2 issues at checkout this morning and was told there was no notes in the file about these things. On a positive note the beds and linens were super, the massage chair was a big hit and the location has lots of restaurants nearby. The manager and staff were extremely friendly and helpful with check in. Fresh baked cookies were a treat. Nice coffee machines in the lobby. Only limited baked goods and some fruit were offered for breakfast."
Nancy 2-night trip
Posted less than an hour ago
Blue – A Modern Hotel, an Ascend Collection Hotel

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is ￥12,109 per night from Jun 17 to Jun 18
￥12,109
￥13,859 total
Jun 17 - Jun 18
includes taxes & fees
6/10 (1,005 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Berkshire Mountain Lodge, located 17.2 mi (27.7 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 Quality Inn West Springfield and D. Hotel Suites & Spa. See all available top hotels, or vacation rentals in Chester.
What are some of the best vacation rentals in Chester?
Cozy Riverside Berkshires Retreat: This vacation home rental outside of Chester is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and an electric kettle, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. 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'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. There are 876 hotels and other accommodations in the surrounding area. 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 Pyramid Lake and Jacob's Pillow 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.

Explore a world of travel with Expedia