Photo by Elizabeth Massa Peroulakis

Chester Hotels

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Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

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Top 10 trending Chester hotels

Exterior
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, (1006)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is €97
includes taxes & fees
10 Dec - 11 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1012)
"Great stay!"
United States
Ann
The price is €60
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (805)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is €106
includes taxes & fees
1 Dec - 2 Dec
Berkshires Untold
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1003)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is €170
includes taxes & fees
21 Dec - 22 Dec
The Cornell Inn, Lenox & The Berkshires
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 star property
West Springfield
8.4 out of 10, Very good, (789)
"Nice, friendly staff, clean room and comfortable suite.. highly recommend "
United States
Christopher
The price is €70
includes taxes & fees
7 Dec - 8 Dec
Candlewood Suites West Springfield by IHG
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is €92
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is €183
includes taxes & fees
16 Dec - 17 Dec
The Red Lion Inn
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very good, (975)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is €89
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
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, (700)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
The price is €103
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Property amenity
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

3.5 star property
South Lee
9.0 out of 10, Wonderful, (792)
"Place was great!"
United States
Benjamin
The price is €115
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Front of property – evening/night
Hotel On North

Hotel On North

3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (801)
"Clean room and staff was super friendly"
United States
Yuen
The price is €128
includes taxes & fees
22 Dec - 23 Dec
Hotel On North
Basic Studio, 1 King Bed
River Valley Inn

River Valley Inn

2.0 star property
West Hatfield
8.6 out of 10, Excellent, (98)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is €105
includes taxes & fees
1 Dec - 2 Dec
River Valley Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (774)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
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, (560)
"The staff were very friendly and accommodating "
United States
Tom
The price is €72
includes taxes & fees
1 Dec - 2 Dec
Travelodge by Wyndham Great Barrington Berkshires
Indoor pool
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3.0 star property
Holyoke
9.4 out of 10, Exceptional, (2273)
"Very clean room, great variety of food at breakfast, friendly and helpful staff."
United States
Liz
The price is €86
includes taxes & fees
3 Dec - 4 Dec
D. Hotel Suites & Spa
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (588)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is €130
includes taxes & fees
7 Dec - 8 Dec
Courtyard by Marriott Lenox Berkshires
Lobby
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

2.5 star property
West Springfield
6.8 out of 10, (1006)
"Great like always "
United States
Sharee
The price is €82
includes taxes & fees
7 Dec - 8 Dec
Red Roof Inn PLUS+ West Springfield
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (757)
"Clean room, very courteous staff "
United States
Thomas
The price is €145
includes taxes & fees
4 Dec - 5 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Indoor pool
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3.0 star property
Metro Center
8.2 out of 10, Very good, (1309)
"Great staff, very clean property, and good breakfast. "
United States
Jasmine
The price is €108
includes taxes & fees
2 Dec - 3 Dec
La Quinta Inn & Suites by Wyndham Springfield MA
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 forests in Chester!

See all hotels in Chester
Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Room was great. Accommodated amenities while I’m adjusting from rough surgery and bad news was a nice surprise and helped lifted my spirits a lot. Come every year on Thanksgiving and always enjoy my stay. This year was gonna tough and like I said, I just told them it was tough for me and they went out of way to make my room fill me with joy and surprise. It just made me happy to know someone put care into everything. I’m grateful. "
Richard 1-night trip
Posted 2 days ago
D. Hotel Suites & Spa

More cheap stays in Chester

Quality Inn West Springfield

Quality Inn West Springfield

1150 Riverdale St West Springfield MA
The price is €83 per night from 14 Dec to 15 Dec
€83
14 Dec - 15 Dec
includes taxes & fees
7/10 Good! (1,019 reviews)

Frequently asked questions

What's the best place to stay in Chester?
La Quinta Inn & Suites by Wyndham Springfield MA, located 22.9 mi (36.8 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 D. Hotel Suites & Spa and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Chester is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. 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 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 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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