Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from AED 220

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Check Chester hotel prices

Tonight
23 Dec - 24 Dec
Tomorrow night
24 Dec - 25 Dec
This weekend
27 Dec - 29 Dec
Next weekend
3 Jan - 5 Jan

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Compare 790 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"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 AED 356
AED 562 total
includes taxes & fees
6 Jan - 7 January 2025
The Red Lion Inn
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1002)
"The hotel was great! The attached AMAZING Indian restaurant was an unexpected treat! "
The price is AED 372
AED 415 total
includes taxes & fees
1 Jan - 2 January 2025
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Exterior

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

3.5 star property
8.6 out of 10, Excellent, (419)
"It was amazing! The staff was incredible, the room was very clean and cozy, and overall was a great place to stay. Loved it here!"
The price is AED 509
AED 569 total
includes taxes & fees
30 Dec - 31 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, (573)
"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 AED 474
AED 581 total
includes taxes & fees
6 Jan - 7 January 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (676)
"Service was good. Great location and good breakfast."
The price is AED 584
AED 652 total
includes taxes & fees
25 Dec - 26 Dec
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
8.8 out of 10, Excellent, (1004)
"the staff was great. rooms where clean there is a bar on site & a bottle of red wine complimentary in the room. a lot in the area unfortunately it was too cold to enjoy a lot of of it"
The price is AED 448
AED 526 total
includes taxes & fees
1 Jan - 2 January 2025
The Cornell Inn, Lenox
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1003)
"Friendly staff"
The price is AED 311
AED 347 total
includes taxes & fees
1 Jan - 2 January 2025
Quality Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (361)
"Everything was amazing. It was truly an experience. "
The price is AED 698
AED 779 total
includes taxes & fees
26 Dec - 27 Dec
Chambery Inn
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (443)
"The location was great, and being pet friendly was a Pius."
The price is AED 281
AED 314 total
includes taxes & fees
6 Jan - 7 January 2025
The Little Lion
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Exterior

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

2.5 star property
8.8 out of 10, Excellent, (577)
"Great comfortable stay. Front desk, breakfast and cleaning staff are the BEST!"
The price is AED 459
AED 513 total
includes taxes & fees
1 Jan - 2 January 2025
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (233)
"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 AED 463
AED 543 total
includes taxes & fees
31 Dec - 1 January 2025
Lakehouse Inn
Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (691)
"went for a quick ski overnight. the motel was very clean, in good shape, quiet, pleasant check in/out experience, free coffee, everything in the room worked, the water was hot the pressure was good there was a fridge and microwave and blowdryer, comfy bed, plenty of hanging closet space, a little table and chair area by the front window, a nice view of the playground, good heating unit, and very convenient to everything you need and want to do here, and most of all affordable including my...
The price is AED 244
AED 273 total
includes taxes & fees
1 Jan - 2 January 2025
Monument Mountain Motel
Little Cat Lodge
Front of property

Little Cat Lodge

2.0 star property
9.0 out of 10, Wonderful, (28)
"Beautiful place"
The price is AED 559
AED 603 total
includes taxes & fees
6 Jan - 7 January 2025
Little Cat Lodge
Blackberry River Inn
Breakfast meal

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 AED 576
AED 662 total
includes taxes & fees
6 Jan - 7 January 2025
Blackberry River Inn
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1002)
"Nice and clean rooms, great variety of free breakfast selections"
The price is AED 309
AED 345 total
includes taxes & fees
5 Jan - 6 January 2025
Quality Inn
Econo Lodge Lee - Great Barrington
Exterior

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 AED 220
AED 246 total
includes taxes & fees
25 Dec - 26 Dec
Econo Lodge Lee - Great Barrington
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 AED 672
AED 751 total
includes taxes & fees
4 Jan - 5 January 2025
Brook Farm Inn
Locust Tree Bed and Breakfast LLC
Exterior

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 AED 386
AED 444 total
includes taxes & fees
25 Dec - 26 Dec
Locust Tree Bed and Breakfast LLC
Whistler's Inn Bed & Breakfast
Interior

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
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (404)
"Quaint "
The price is AED 386
AED 423 total
includes taxes & fees
5 Jan - 6 January 2025
Shaker Mill 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 traveler data. Other good choices for your trip to the area are La Quinta Inn & Suites by Wyndham Springfield MA and Life House Berkshires. See all available top hotels, or vacation rentals in Chester.

What are some of the best vacation rentals in Chester?

Berkshire Village Carriage House - Super Private!!: This vacation home rental outside of Chester is located in the mountains and has a garden, a barbecue grill, 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 the 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! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

For additional details about picking new dates or cancelling your trip to Chester, go to https://www.expedia.com/service/.

What's the best accommodation near Logan International Airport (BOS)?

Hilton Boston Logan Airport is a popular 4-star hotel featuring a restaurant and an indoor pool. It's located a short 0.2 mi (0.4 km) from Logan Intl. Airport. Other accommodations close to the airport are Hyatt Regency Boston Harbor and Embassy Suites Boston Logan Airport.

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, theaters, and monuments. In Chester, there are 2 hotels and other accommodations to choose from. Find out more about Chester.

What should I see while I'm in Chester?

A favorite place to visit is Chester Town Hall. You'll also find Glendale Falls and Iroquis Waterfront in the area. Check out what more to see and do in Expedia's Chester guide.

What's the seasonal weather like in Chester?

The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.