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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, (891 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is NZ$180
includes taxes & fees
9 Apr - 10 Apr
Berkshires Untold

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (838 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is NZ$117
includes taxes & fees
8 Apr - 9 Apr
Monument Mountain Motel

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 NZ$217
includes taxes & fees
21 Apr - 22 Apr
Best Western Plus Berkshire Hills Inn & Suites

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (127 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is NZ$213
includes taxes & fees
9 Apr - 10 Apr
River Valley Inn

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 NZ$280
includes taxes & fees
13 Apr - 14 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, (159 reviews)
"So close to the Big E Fairgroynds, wonderful service, would stay again!"
United States
Terry
The price is NZ$204
includes taxes & fees
29 Apr - 30 Apr
Baldwin Inn & Suites, SureStay Collection by Best Western

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.8 out of 10, Exceptional, (77 reviews)
"The check in staff were amazing "
United States
mandeep
The price is NZ$298
includes taxes & fees
20 Apr - 21 Apr
TownePlace Suites by Marriott Hadley Amherst

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2,231 reviews)
"Very clean, comfortable, and quiet hotel. We enjoyed our visit."
United States
Larry
The price is NZ$250
includes taxes & fees
22 Apr - 23 Apr
D. Hotel Suites & Spa

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (431 reviews)
"Breakfast was exceptional. We couldn’t have been happier during our stay."
United States
Robert
The price is NZ$222
includes taxes & fees
12 Apr - 13 Apr
Naomi's Inn Bed & Breakfast

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 visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is NZ$198
includes taxes & fees
21 Apr - 22 Apr
Quality Inn Lee - Lenox South

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, (1,003 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is NZ$200
includes taxes & fees
23 Apr - 24 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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 NZ$215
includes taxes & fees
9 Apr - 10 Apr
The Little Lion

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is NZ$137
includes taxes & fees
8 Apr - 9 Apr
Pleasant Valley Motel West Stockbridge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (896 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is NZ$209
includes taxes & fees
7 May - 8 May
Berkshire Mountain Lodge

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
The price is NZ$259
includes taxes & fees
12 Apr - 13 Apr
Hideaway Inn Lenox

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,005 reviews)
"Best hotel in area."
United States
William
The price is NZ$210
includes taxes & fees
21 Apr - 22 Apr
Tru by Hilton Chicopee Springfield

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, (754 reviews)
"Staff was great! Clean room, parking was always available. Breakfast was great. Had a great time!"
United States
Brigid
The price is NZ$225
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (575 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NZ$147
includes taxes & fees
15 Apr - 16 Apr
Travelodge by Wyndham Great Barrington Berkshires

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (625 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is NZ$248
includes taxes & fees
22 Apr - 23 Apr
Fairfield Inn & Suites Springfield Holyoke

Hampton Inn Westfield

Hampton Inn Westfield
2.5 star property
Westfield
8.4 out of 10, Very good, (840 reviews)
"We had an excellent experience all around. "
United States
Jennifer
The price is NZ$231
includes taxes & fees
19 Apr - 20 Apr
Hampton Inn Westfield
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 waterfalls in Chester!

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Top Chester Hotel Reviews

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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.
What are some of the best holiday rentals that Chester has to offer?
Cozy Riverside Berkshires Retreat: This holiday home rental outside of Chester is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 Pyramid Lake and Skyline Trail 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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