Search 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
21 Feb - 22 Feb
Tomorrow
22 Feb - 23 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 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, (117 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 NZ$167
includes taxes & fees
26 Feb - 27 Feb
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, (1,002 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is NZ$179
includes taxes & fees
2 Mar - 3 Mar
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, (1,004 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is NZ$166
includes taxes & fees
9 Mar - 10 Mar
Quality Inn Lee - Lenox South
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is NZ$260
includes taxes & fees
2 Mar - 3 Mar
Element Lenox Berkshires
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (613 reviews)
"Room was spotless, staff were nice. "
United States
Jose I Medina
The price is NZ$206
includes taxes & fees
22 Feb - 23 Feb
Fairfield Inn & Suites Springfield Holyoke
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
9.2 out of 10, Wonderful, (2,232 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, (111 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is NZ$185
includes taxes & fees
23 Feb - 24 Feb
River Valley Inn
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,003 reviews)
"Friendly clean accommodation were just what we needed. "
United States
Carrie
The price is NZ$185
includes taxes & fees
1 Mar - 2 Mar
Tru by Hilton Chicopee Springfield
Lobby

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
West Springfield
9.4 out of 10, Exceptional, (150 reviews)
"Exceptionally clean, loved the massage chair and free shampoo .. the beds were so comfy!"
United States
Jackie
The price is NZ$221
includes taxes & fees
24 Feb - 25 Feb
Blue – A Modern Hotel, an Ascend Collection Hotel
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)
"The room was great and jose at the front desk was very kind amd helpful and at the breakfast department he was great."
United States
LUIS
The price is NZ$169
includes taxes & fees
24 Feb - 25 Feb
Best Western Springfield West Inn
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, (736 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is NZ$193
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (917 reviews)
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
United States
Gloria
The price is NZ$173
includes taxes & fees
11 Mar - 12 Mar
Quality Inn Westfield - Springfield
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (828 reviews)
"I will stay again"
United States
Jailene
The price is NZ$204
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn Westfield
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, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is NZ$129
includes taxes & fees
23 Feb - 24 Feb
Howard Johnson by Wyndham Lenox
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 NZ$187
includes taxes & fees
1 Mar - 2 Mar
Hampton Inn West Springfield
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 NZ$107
includes taxes & fees
24 Feb - 25 Feb
Pleasant Valley Motel West Stockbridge
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,008 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is NZ$173
includes taxes & fees
2 Mar - 3 Mar
The Yankee, Trademark Collection by Wyndham
Lobby

Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst
3.0 star property
Northampton
9.2 out of 10, Wonderful, (1,002 reviews)
"Nice hotel "
United States
Irfan
The price is NZ$252
includes taxes & fees
8 Mar - 9 Mar
Fairfield Inn & Suites Springfield Northampton/Amherst
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (972 reviews)
"clean room, nice staff"
United States
david
The price is NZ$250
includes taxes & fees
1 Mar - 2 Mar
The Ellery
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

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"great customer service"
Edward 2-night trip
Posted 3 days ago
The Red Lion Inn

More cheap accommodation in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is NZ$135 per night from 1 Mar to 2 Mar
NZ$135
1 Mar - 2 Mar
includes taxes & fees
5.8/10 (1,002 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?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Chester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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 selection of games and 1 hot tub. 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 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 Becket Land Trust Historic Quarry and Littleville 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