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Chester Hotels

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Check prices for these dates

This weekend
17 Jul - 19 Jul
Next weekend
24 Jul - 26 Jul

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Our top choices for Chester hotels

Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (61 reviews)
"Comfortable stay "
United States
Paul
The price is €146
includes taxes & fees
19 Jul - 20 Jul
Becket Motel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"Great place"
United States
Michelle
The price is €129
includes taxes & fees
20 Jul - 21 Jul
Quality Inn Lee - Lenox South
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is €175
includes taxes & fees
19 Jul - 20 Jul
The Yankee Inn
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)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is €115
includes taxes & fees
4 Aug - 5 Aug
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (882 reviews)
"Nice hotel for an overnight trip. Staff was very friendly and helpful."
United States
Brian
The price is €127
includes taxes & fees
28 Jul - 29 Jul
Hampton Inn Westfield
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (425 reviews)
"It was a great stay, close to many amenities. The room was clean, with a comfortable bed."
Canada
Kevin
The price is €96
includes taxes & fees
22 Jul - 23 Jul
Sunset Inn
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, (137 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is €162
includes taxes & fees
22 Jul - 23 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires 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, (962 reviews)
"The coffee was fantastic. Rooms were quiet"
United States
Richard
The price is €99
includes taxes & fees
9 Aug - 10 Aug
Quality Inn Westfield - Springfield
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.4 out of 10, Exceptional, (6 reviews)
"Everything was perfect!!"
United States
Grzegorz
The price is €204
includes taxes & fees
28 Jul - 29 Jul
Berkshire Lake Lodge
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,019 reviews)
"Amazing place to stay and fantastic location. Already wanting to plan my next trip!"
United States
Tara
The price is €148
includes taxes & fees
12 Aug - 13 Aug
The Ellery
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, (885 reviews)
"Great place"
United States
Luciane
The price is €96
includes taxes & fees
26 Jul - 27 Jul
Howard Johnson by Wyndham Lenox
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (855 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
United States
DAVID
The price is €60
includes taxes & fees
9 Aug - 10 Aug
FairBridge Inn Express
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (676 reviews)
"Good location to towns in area"
United States
William
The price is €82
includes taxes & fees
10 Aug - 11 Aug
Econo Lodge Lee - Great Barrington
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
"Fantastic pool to top off the great location and fun historic hotel!"
United States
Antoinette G.
The price is €220
includes taxes & fees
29 Jul - 30 Jul
The Red Lion Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (880 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
The price is €88
includes taxes & fees
19 Jul - 20 Jul
Berkshire Inn
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.2 out of 10, Wonderful, (936 reviews)
"Wonderful stay for families."
United States
Kimberly
The price is €182
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (791 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is €145
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Studio Suite, Multiple Beds

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (187 reviews)
"It's a really nice place to stay!"
United States
Vidita
The price is €107
includes taxes & fees
29 Jul - 30 Jul
River Valley Inn
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, (1,003 reviews)
"enjoyable stay"
United States
James
The price is €208
includes taxes & fees
23 Jul - 24 Jul
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Children’s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Very comfortable. Will stay there again"
United States
Peter
The price is €65
includes taxes & fees
19 Jul - 20 Jul
Pleasant Valley Motel West Stockbridge
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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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 riverfront in Chester!

See all hotels in Chester
A stone bridge over a flowing river with rocks and autumn foliage.
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

Frequently asked questions

What's the best place to stay in Chester?
Quality Inn West Springfield, located 20.6 mi (33.1 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 La Quinta Inn & Suites by Wyndham Springfield MA and The Yankee Inn. 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 5 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. There are 877 hotels and other accommodation options in the surrounding area. 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 Glendale Falls 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.

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