Photo by Elizabeth Massa Peroulakis

Chester Hotels

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Check Chester hotel prices

Tonight
19 Dec - 20 Dec
Tomorrow night
20 Dec - 21 Dec
This weekend
20 Dec - 22 Dec
Next weekend
27 Dec - 29 Dec

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Top 10 trending Chester hotels

The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"It is one of the oldest inns in America - so it creaks a lot, uneven floors, and for sure that look of old.. not necessarily bad... just a heritage property that has its quirks. We liked it.. the bed could be better for sure... I think that's the main fault.. the restaurant and pub were wonderful, good food and service. The common, fireplace room ambiance was nice. "
The price is €151
includes taxes & fees
1 Jan - 2 Jan 2025
The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Lobby

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Good "
The price is €108
includes taxes & fees
2 Jan - 3 Jan 2025
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Free WiFi, bed sheets

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (413)
"Cute hotel in a beautiful town. Convenient location."
The price is €165
includes taxes & fees
26 Dec - 27 Dec
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 star property
9.0 out of 10, Wonderful, (571)
"Westayed at the resort for the Stockbridge Christmas weekend location was so convenient to town, dining and events, Resort facilities were extra special pool movie theatre and resort Christmas themed activities would recommend."
The price is €151
includes taxes & fees
6 Jan - 7 Jan 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Cornell Inn, Lenox
Porch

The Cornell Inn, Lenox

3.0 star property
8.8 out of 10, Excellent, (1002)
"Beautiful place to stay - loved it - interior decor first rate! "
The price is €138
includes taxes & fees
12 Jan - 13 Jan 2025
The Cornell Inn, Lenox
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (673)
"Staff are very nice and accommodating. Self parking is safe and easy. Rooms are always clean and comfortable. "
The price is €169
includes taxes & fees
22 Dec - 23 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn
Standard Room, 2 Queen Beds, Non Smoking

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Friendly staff"
The price is €91
includes taxes & fees
25 Dec - 26 Dec
Quality Inn
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (442)
"It was so convenient to check in. They send a code for the door, so it was super helpful when I am checking in later in the evening. Parking right outside my door. The room was super cute and nicely warm on a very cold day. The one issue I had was the walls are very thin so I could hear every conversation in the room next door, and was woken up by screaming children. "
The price is €81
includes taxes & fees
1 Jan - 2 Jan 2025
The Little Lion
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (360)
"What an amazing room! From the canopied bed to the cozy gas fireplace. Not to mention that it is the most spacious room you could imagine! The breakfast basket was amazing, too! "
The price is €202
includes taxes & fees
26 Dec - 27 Dec
Chambery Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (574)
"Convenient hotel."
The price is €129
includes taxes & fees
12 Jan - 13 Jan 2025
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (232)
"We really enjoyed our stay. The breakfast was really good and the added touch of a welcome drink was really fun and made our stay feel special. We would like to come back again. "
The price is €153
includes taxes & fees
20 Dec - 21 Dec
Lakehouse Inn
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (687)
"Clean, friendly, and good location. "
The price is €71
includes taxes & fees
22 Dec - 23 Dec
Monument Mountain Motel
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.0 out of 10, Wonderful, (28)
"Beautiful place"
The price is €159
includes taxes & fees
5 Jan - 6 Jan 2025
Little Cat Lodge
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (95)
"Very clean. The host was friendly and attentive. Great complimentary breakfast. Clean,quiet and very comfortable. "
The price is €174
includes taxes & fees
2 Jan - 3 Jan 2025
Blackberry River Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (581)
"Was convenient and inexpensive. The back stairs were a little rickety. Also had to ring the bell to check in later in the evening, but was fine. Room was just the basics, but served the purpose for my one night stay. "
The price is €64
includes taxes & fees
23 Dec - 24 Dec
Econo Lodge Lee - Great Barrington
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Nice and clean rooms, great variety of free breakfast selections"
The price is €90
includes taxes & fees
5 Jan - 6 Jan 2025
Quality Inn
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is €184
includes taxes & fees
22 Dec - 23 Dec
Brook Farm Inn
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (373)
"Very pretty setting and house. Comfortable bed. Nice view Would have liked bottled water available in the room. Breakfast was nice."
The price is €115
includes taxes & fees
27 Dec - 28 Dec
Locust Tree Bed and Breakfast LLC
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast
East Rock Inn
Exterior

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (13)
"Love this motel. Visit the area monthly, this was my 5th visit at East Rock, every time has been perfect."
The price is €125
includes taxes & fees
1 Jan - 2 Jan 2025
East Rock Inn
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?

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 La Quinta Inn & Suites by Wyndham Springfield MA 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?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Chester is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind. 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 are some hotels with pools in Chester?

La Quinta Inn & Suites by Wyndham Springfield MA: 3-star hotel located near Springfield Museums. Offers a children's pool, an indoor pool and a snack bar. Tru by Hilton Chicopee Springfield and D. Hotel Suites & Spa are two additional hotels that offer an on-site pool. View all hotels with pools 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 2 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 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.