Chester Hotels

  • 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

Tonight
1 Mar - 2 Mar
Tomorrow
2 Mar - 3 Mar
Next weekend
6 Mar - 8 Mar
In two weeks
13 Mar - 15 Mar

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chester hotels

Standard Room, 2 Queen Beds, Non Smoking

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, (121 reviews)
"Clean room and very spacious, staff was friendly, i would only add a small dinning table to the room. "
United States
Tomarie
The price is €85
includes taxes & fees
3 Mar - 4 Mar
Baldwin Inn & Suites, SureStay Collection by Best Western
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,000 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is €91
includes taxes & fees
2 Mar - 3 Mar
Best Western Plus Berkshire Hills Inn & Suites
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (21 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is €131
includes taxes & fees
8 Mar - 9 Mar
Element Lenox Berkshires
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is €81
includes taxes & fees
22 Mar - 23 Mar
Quality Inn Lee - Lenox South
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
Terrace/patio

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,207 reviews)
"Great service, clean & quiet rooms, and a solid breakfast to start the day"
United States
Stephanie
D. Hotel Suites & Spa
Exterior

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (115 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is €94
includes taxes & fees
2 Mar - 3 Mar
River Valley Inn
In-room safe, desk, free cots/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, (573 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is €71
includes taxes & fees
2 Mar - 3 Mar
Travelodge by Wyndham Great Barrington Berkshires
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (741 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is €101
includes taxes & fees
5 Mar - 6 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (614 reviews)
"Room was spotless, staff were nice. "
United States
Jose I Medina
The price is €112
includes taxes & fees
16 Mar - 17 Mar
Fairfield Inn & Suites Springfield Holyoke
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (976 reviews)
"clean room, nice staff"
United States
david
The price is €117
includes taxes & fees
10 Mar - 11 Mar
The Ellery
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is €54
includes taxes & fees
3 Mar - 4 Mar
Pleasant Valley Motel West Stockbridge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (865 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
The price is €95
includes taxes & fees
2 Mar - 3 Mar
Berkshires Untold
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
United States
Anindita
The price is €92
includes taxes & fees
22 Mar - 23 Mar
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (829 reviews)
"I will stay again"
United States
Jailene
The price is €108
includes taxes & fees
22 Mar - 23 Mar
Hampton Inn Westfield
Free daily full breakfast

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (428 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is €97
includes taxes & fees
15 Mar - 16 Mar
Naomi's Inn Bed & Breakfast
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,002 reviews)
"Friendly clean accommodation were just what we needed. "
United States
Carrie
The price is €102
includes taxes & fees
8 Mar - 9 Mar
Tru by Hilton Chicopee Springfield
Lobby

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very good, (1,000 reviews)
"Very good place to stay"
United States
Gloria
The price is €102
includes taxes & fees
3 Mar - 4 Mar
Hampton Inn West Springfield
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (84 reviews)
"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."
United States
Laura Pearson
The price is €125
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (845 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is €81
includes taxes & fees
1 Apr - 2 Apr
Berkshire Inn
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 on your trip to Chester. Wander the lakeside and forests in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping and waterfalls in Chester!

See all hotels in Chester
An amazing keystone arch bridge!
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Overall pleasant stay; great facilities, staff, and location"
Casey 2-night trip
Posted 5 days ago
Berkshire Mountain Lodge

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is €71 per night from 2 Mar to 3 Mar
€71
2 Mar - 3 Mar
includes taxes & fees
5.8/10 (999 reviews)

Frequently asked questions

What's the best place to stay in Chester?
D. Hotel Suites & Spa, located 19.1 mi (30.7 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 Berkshire Mountain Lodge and The Yankee, Trademark Collection by Wyndham. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Chester is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 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, 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 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 3 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 Littleville Lake 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.

Explore a world of travel with Expedia