Chester Hotels

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Check prices for these dates

Tonight
16 Apr - 17 Apr
Tomorrow
17 Apr - 18 Apr
This weekend
17 Apr - 19 Apr
Next weekend
24 Apr - 26 Apr

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Our top choices for Chester hotels

Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (899 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 €74
includes taxes & fees
27 Apr - 28 Apr
Berkshires Untold
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (840 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is €57
includes taxes & fees
23 Apr - 24 Apr
Monument Mountain Motel
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, (1,004 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 €96
includes taxes & fees
21 Apr - 22 Apr
Best Western Plus Berkshire Hills Inn & Suites
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, (79 reviews)
"The check in staff were amazing "
United States
mandeep
The price is €144
includes taxes & fees
30 Apr - 1 May
TownePlace Suites by Marriott Hadley Amherst
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, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is €66
includes taxes & fees
18 Apr - 19 Apr
Pleasant Valley Motel West Stockbridge
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (906 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is €97
includes taxes & fees
19 Apr - 20 Apr
Berkshire Mountain Lodge
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 €139
includes taxes & fees
22 Apr - 23 Apr
Element Lenox Berkshires
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, (166 reviews)
"So close to the Big E Fairgroynds, wonderful service, would stay again!"
United States
Terry
The price is €106
includes taxes & fees
26 Apr - 27 Apr
Baldwin Inn & Suites, SureStay Collection by Best Western
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, (849 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is €75
includes taxes & fees
18 Apr - 19 Apr
Howard Johnson by Wyndham Lenox
Room (Louis XIV)

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (432 reviews)
"Breakfast was exceptional. We couldn’t have been happier during our stay."
United States
Robert
The price is €108
includes taxes & fees
19 Apr - 20 Apr
Naomi's Inn Bed & Breakfast
Studio Suite, Multiple Beds

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (130 reviews)
"Friendly staff, really nice room, quiet. I really enjoyed my stay."
United States
Desiree
The price is €103
includes taxes & fees
19 Apr - 20 Apr
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
9.0 out of 10, Wonderful, (1,000 reviews)
"Room was spotless, staff was very kind!"
United States
Ilia
The price is €96
includes taxes & fees
28 Apr - 29 Apr
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 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 €96
includes taxes & fees
3 May - 4 May
Quality Inn Lee - Lenox South
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (852 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is €76
includes taxes & fees
4 May - 5 May
Berkshire Inn
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, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is €71
includes taxes & fees
17 Apr - 18 Apr
Travelodge by Wyndham Great Barrington Berkshires
Exterior

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 €104
includes taxes & fees
20 Apr - 21 Apr
The Little Lion
View from property

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (629 reviews)
"We enjoyed our 3 nights it was quiet and very clean "
United States
Joanne
The price is €115
includes taxes & fees
4 May - 5 May
Fairfield Inn & Suites Springfield Holyoke
Lobby

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,002 reviews)
"Best hotel in area."
United States
William
The price is €110
includes taxes & fees
6 May - 7 May
Tru by Hilton Chicopee Springfield
Free daily buffet breakfast

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield
2.5 star property
Westfield
7.2 out of 10, Good, (921 reviews)
"Everything clean "
United States
GLADYS
The price is €87
includes taxes & fees
10 May - 11 May
Quality Inn Westfield - Springfield
Front of property

The Ellery

The Ellery
3.5 star property
Northampton
9.2 out of 10, Wonderful, (1,011 reviews)
"Really liked staying here and will come back when I am in the area again!"
United States
William
The price is €151
includes taxes & fees
28 Apr - 29 Apr
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 waterfalls in Chester!

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

Top Chester Hotel Reviews

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

10/10 Excellent
"Great"
Vanessa 2-night trip
Posted 15 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
The price is €86 per night from 30 Apr to 1 May
€86
30 Apr - 1 May
includes taxes & fees
7/10 Good! (1,013 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 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 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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