Chester Hotels from S$90

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Check prices for these dates

Tonight
9 May - 10 May
Tomorrow
10 May - 11 May
Next weekend
15 May - 17 May
In two weeks
22 May - 24 May

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Our top choices for Chester hotels

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)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is S$156
includes taxes & fees
11 May - 12 May
Best Western Plus Berkshire Hills Inn & Suites
Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is S$140
includes taxes & fees
13 May - 14 May
The Yankee Inn
Pillow-top beds, desk, laptop workspace, blackout curtains

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
West Springfield
8.0 out of 10, Very good, (177 reviews)
"Bed was comfy room was clean woman at front desk was cheerful."
United States
Kathleen
The price is S$158
includes taxes & fees
12 May - 13 May
Baldwin Inn & Suites, SureStay Collection by Best Western
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (639 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is S$180
includes taxes & fees
1 Jun - 2 Jun
Fairfield Inn & Suites Springfield Holyoke
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (932 reviews)
"Great stay!"
United States
Aditya
The price is S$161
includes taxes & fees
14 May - 15 May
Berkshires Untold
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is S$97
includes taxes & fees
13 May - 14 May
Monument Mountain Motel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,004 reviews)
"Great location "
United States
Edith
The price is S$156
includes taxes & fees
19 May - 20 May
Quality Inn Lee - Lenox South
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is S$236
includes taxes & fees
27 May - 28 May
Element Lenox Berkshires
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,012 reviews)
"Great place"
United States
William
The price is S$160
includes taxes & fees
2 Jun - 3 Jun
Tru by Hilton Chicopee Springfield
Premium bedding, desk, laptop workspace, blackout curtains

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (852 reviews)
"Yes to both plus easy access to Turnpike"
United States
Karen
The price is S$171
includes taxes & fees
27 May - 28 May
Hampton Inn Westfield
Desk, laptop workspace, free WiFi, bed sheets

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (146 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is S$137
includes taxes & fees
9 Jun - 10 Jun
River Valley Inn
Individually decorated, individually furnished, iron/ironing board

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.2 out of 10, Wonderful, (435 reviews)
"We really enjoyed our brief stay at Naomi's. It's a real Bed and Breakfast, with real home-made breakfast, great coffee, and an old-time charm that you really have to search for these days. The recommendation of where to eat was also spot-on. Will stay again."
United States
Daniel
The price is S$170
includes taxes & fees
17 May - 18 May
Naomi's Inn Bed & Breakfast
Property amenity

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (86 reviews)
"Clean room, good breakfast and friendly staff."
Canada
Michelle
The price is S$248
includes taxes & fees
31 May - 1 Jun
TownePlace Suites by Marriott Hadley Amherst
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, (760 reviews)
"Nice clean room, clean and well maintained breakfast was tasteful each day. Desk Clerk very helpful in giving out direction, Breaksfast person, very friendly. Hotel is centrally located, shop and restaurant nearby"
United States
Berdest
The price is S$176
includes taxes & fees
27 May - 28 May
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (925 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is S$153
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge
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, (1,003 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is S$87
includes taxes & fees
26 May - 27 May
Pleasant Valley Motel West Stockbridge
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, (578 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 S$106
includes taxes & fees
10 May - 11 May
Travelodge by Wyndham Great Barrington Berkshires
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, (853 reviews)
"Great value"
United States
Ralph
The price is S$112
includes taxes & fees
10 May - 11 May
Howard Johnson by Wyndham Lenox
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,005 reviews)
"Staff was friendly, room was clean and the beds were comfortable. Dog friendly also. Good breakfast selection. I would stay there again."
United States
Lillian
The price is S$173
includes taxes & fees
27 May - 28 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,007 reviews)
"Excellent breakfast, clean room, good location, quiet, friendly and helpful staff, comfortable bed."
United States
Susan
The price is S$191
includes taxes & fees
26 May - 27 May
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.
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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 monuments in Chester!

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

Top Chester Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Everything was great"
Riri 2-night trip
Posted 7 hours ago
The Red Lion Inn

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is S$106 per night from 25 May to 26 May
S$106
25 May - 26 May
includes taxes & fees
6/10 (1,002 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 traveller data. Other good choices for your visit to the area are Berkshires Untold and D. Hotel Suites & Spa. See all available top hotels, or 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 873 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 Glendale Falls 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.

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