Chester Hotels

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Our top choices for Chester hotels

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is €120
includes taxes & fees
29 Jun - 30 Jun
The Yankee Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (859 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
The price is €74
includes taxes & fees
3 Jun - 4 Jun
Monument Mountain Motel

D. Hotel Suites & Spa

D. Hotel Suites & Spa
3.0 star property
Holyoke
9.2 out of 10, Wonderful, (2,194 reviews)
"Spacious room, very helpful staff, good coffee and an excellent breakfast."
United States
Clifford
The price is €96
includes taxes & fees
14 Jun - 15 Jun
D. Hotel Suites & Spa

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,002 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is €108
includes taxes & fees
4 Jun - 5 Jun
Quality Inn Lee - Lenox South

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, (194 reviews)
"Front desk staff was very friendly and informative. Great location for the local colleges."
United States
Chris
The price is €109
includes taxes & fees
8 Jun - 9 Jun
Baldwin Inn & Suites, SureStay Collection by Best Western

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (162 reviews)
"Friendly staff, great under the radar spot alternative to chain motels!"
United States
Anthony
The price is €97
includes taxes & fees
3 Jun - 4 Jun
River Valley Inn

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
The price is €126
includes taxes & fees
2 Jun - 3 Jun
Berkshire Lake Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (100 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is €126
includes taxes & fees
7 Jun - 8 Jun
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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)
"clean room, friendly staff, great breakfast"
United States
charles
The price is €105
includes taxes & fees
15 Jun - 16 Jun
Best Western Plus Berkshire Hills Inn & Suites

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (442 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is €115
includes taxes & fees
3 Jun - 4 Jun
Naomi's Inn Bed & Breakfast

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (966 reviews)
"Friendly good location"
United States
Vivian
The price is €103
includes taxes & fees
7 Jun - 8 Jun
Berkshires Untold

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is €68
includes taxes & fees
2 Jun - 3 Jun
Pleasant Valley Motel West Stockbridge

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (862 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is €76
includes taxes & fees
2 Jun - 3 Jun
Howard Johnson by Wyndham Lenox

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (859 reviews)
"Great stay "
United States
Brian
The price is €82
includes taxes & fees
2 Jun - 3 Jun
Berkshire Inn

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (581 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 €76
includes taxes & fees
2 Jun - 3 Jun
Travelodge by Wyndham Great Barrington Berkshires

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is €95
includes taxes & fees
3 Jun - 4 Jun
The Little Lion

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
West Springfield
8.2 out of 10, Very good, (1,002 reviews)
"Our room was very clean, staff was very friendly. We would stay here again."
United States
Sherry
The price is €88
includes taxes & fees
9 Jun - 10 Jun
Hampton Inn West Springfield

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (820 reviews)
"Scammers!! I booked a night just to shower and refresh. An abandoned public bathroom is 100 times cleaner than their room"
United States
Elie
The price is €68
includes taxes & fees
14 Jun - 15 Jun
FairBridge Inn Express

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (3 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
The price is €110
includes taxes & fees
2 Jun - 3 Jun
Hideaway Inn Lenox

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (960 reviews)
"Great location and resort. Very happy with accommodation's"
United States
Robert
The price is €136
includes taxes & fees
2 Jun - 3 Jun
Berkshire Mountain Lodge
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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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 Quality Inn West Springfield. 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. There are 870 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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