Chester Hotels from S$84

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Our top choices for Chester hotels

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (880 reviews)
"Beautiful little quaint hotel. I will definitely be returning"
United States
Erin
The price is S$99
includes taxes & fees
2 Apr - 3 Apr
Berkshires Untold

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (24 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is S$198
includes taxes & fees
31 Mar - 1 Apr
Element Lenox Berkshires

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, (140 reviews)
"So close to the Big E Fairgroynds, wonderful service, would stay again!"
United States
Terry
The price is S$148
includes taxes & fees
2 Apr - 3 Apr
Baldwin Inn & Suites, SureStay Collection by Best Western

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (834 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
Monument Mountain Motel

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (120 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is S$141
includes taxes & fees
26 Mar - 27 Mar
River Valley Inn

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)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is S$152
includes taxes & fees
26 Mar - 27 Mar
Best Western Plus Berkshire Hills Inn & Suites

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (75 reviews)
"Everything is great here and pet friendly :) "
United States
Jonathan
The price is S$217
includes taxes & fees
2 Apr - 3 Apr
TownePlace Suites by Marriott Hadley Amherst

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is S$82
includes taxes & fees
26 Mar - 27 Mar
Pleasant Valley Motel West Stockbridge

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)
"Cleanliness, staff courtesy, breakfast."
United States
Chris
The price is S$120
includes taxes & fees
7 Apr - 8 Apr
Quality Inn Lee - Lenox South

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (430 reviews)
"So cute and accommodating to our schedule "
United States
Carey Lynn
The price is S$149
includes taxes & fees
26 Mar - 27 Mar
Naomi's Inn Bed & Breakfast

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,221 reviews)
"This has become our company's preferred hotel for business trips to the Holyoke/Northampton area. It is clean, quiet, safe, convenient, and the breakfast is stellar."
United States
Alexander
The price is S$162
includes taxes & fees
30 Mar - 31 Mar
D. Hotel Suites & Spa

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,006 reviews)
"Friendly clean accommodation were just what we needed. "
United States
Carrie
The price is S$153
includes taxes & fees
2 Apr - 3 Apr
Tru by Hilton Chicopee Springfield

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (620 reviews)
"staff is nice and kind"
United States
Wanjiang
The price is S$168
includes taxes & fees
29 Mar - 30 Mar
Fairfield Inn & Suites Springfield Holyoke

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
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$132
includes taxes & fees
31 Mar - 1 Apr
The Yankee, Trademark Collection by Wyndham

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (574 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is S$107
includes taxes & fees
27 Mar - 28 Mar
Travelodge by Wyndham Great Barrington Berkshires

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 S$154
includes taxes & fees
29 Mar - 30 Mar
Hampton Inn West Springfield

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is S$157
includes taxes & fees
26 Mar - 27 Mar
The Little Lion

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, (750 reviews)
"Simple and clean hotel"
United States
Vitor
The price is S$152
includes taxes & fees
30 Mar - 31 Mar
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (885 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is S$158
includes taxes & fees
26 Mar - 27 Mar
Berkshire Mountain Lodge

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, (1,000 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is S$136
includes taxes & fees
13 Apr - 14 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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

Learn more about Chester

Experience the hiking, camping and monuments in Chester!

An amazing keystone arch bridge!
Photo by Chris Addams
Open Photo by Chris Addams

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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 Berkshires Untold. 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. 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 Pyramid Lake and Jacob's Pillow 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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