Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from SAR 225

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Check Chester hotel prices

Tonight
23 Dhuʻl-Q. - 24 Dhuʻl-Q.
Tomorrow night
24 Dhuʻl-Q. - 25 Dhuʻl-Q.
Next weekend
29 Dhuʻl-Q. - 1 Dhuʻl-H.

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Compare 785 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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, (1012)
"Great stay"
The price is SAR 357
SAR 399 total
includes taxes & fees
9 Dec - 10 Dec
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
Front of property

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1020)
"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. The dinner was delicious. Plenty of seats but gave us a table facing wall (but near window) —why not more in middle of room area with more interesting view! And same table for breakfast and...
The price is SAR 563
SAR 797 total
includes taxes & fees
1 Dec - 2 Dec
The Red Lion Inn
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, (568)
"The unit was perfect in size, very good quality of towels. For the cribs, they provided new sheets and blanket that was important for us. "
The price is SAR 381
SAR 478 total
includes taxes & fees
26 Nov - 27 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Terrace/patio

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

3.5 star property
8.6 out of 10, Excellent, (404)
"This was a comfortable, clean room in a great little shopping and dining neighborhood. The staff was very friendly and helpful. I look forward to staying here again! "
The price is SAR 366
SAR 409 total
includes taxes & fees
25 Nov - 26 Nov
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Little Lion
Exterior

The Little Lion

3.0 star property
8.8 out of 10, Excellent, (435)
"this is a great little roadside motel that is perfect for road trips. clean and convenient. close to hoking if you like. minimal but totally fine. it’s what you want on a road trip"
The price is SAR 276
SAR 308 total
includes taxes & fees
8 Dec - 9 Dec
The Little Lion
The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
8.8 out of 10, Excellent, (1035)
"We were greeted warmly upon arrival with hot beverages and brownies. There were bakery items available all during our stay, and the property features a quaint little bar with many offerings. The breakfast was served in a bright and very well-appointed room with a fireplace and the staff were very friendly and attentive. The food was very nicely presented and delicious. This is a wonderful bed and breakfast at a very affordable price. Will definitely return. "
The price is SAR 458
SAR 537 total
includes taxes & fees
25 Nov - 26 Nov
The Cornell Inn, Lenox
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1054)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman "
The price is SAR 267
SAR 299 total
includes taxes & fees
8 Dec - 9 Dec
Quality Inn
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is SAR 589
SAR 691 total
includes taxes & fees
20 Dec - 21 Dec
Lakehouse Inn
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, (672)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is SAR 571
SAR 637 total
includes taxes & fees
26 Nov - 27 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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, (564)
"Look clean, great staffs."
The price is SAR 443
SAR 495 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is SAR 713
SAR 797 total
includes taxes & fees
24 Nov - 25 Nov
Chambery Inn
Blackberry River Inn
Breakfast meal

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (91)
"The room with bathroom was very comfortable and clean. The property was extensive and well maintained. Breakfast choices were extensive and our choices were delicious and cooked by Lucas."
The price is SAR 589
SAR 661 total
includes taxes & fees
25 Nov - 26 Nov
Blackberry River Inn
Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (678)
"Nice people operating a very clean, comfortable motel. A bargain."
The price is SAR 250
SAR 279 total
includes taxes & fees
24 Nov - 25 Nov
Monument Mountain Motel
Little Cat Lodge
Front of property

Little Cat Lodge

2.0 star property
9.0 out of 10, Wonderful, (27)
"Loved the place just go! "
The price is SAR 635
SAR 685 total
includes taxes & fees
24 Nov - 25 Nov
Little Cat Lodge
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1024)
"Clean and quiet. Easy check in. Nice breakfast "
The price is SAR 297
SAR 332 total
includes taxes & fees
8 Dec - 9 Dec
Quality Inn
Locust Tree Bed and Breakfast LLC
Exterior

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (367)
"Nice room at reasonable price with breakfast included. "
The price is SAR 394
SAR 453 total
includes taxes & fees
24 Nov - 25 Nov
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...
The price is SAR 614
SAR 758 total
includes taxes & fees
8 Dec - 9 Dec
Whistler's Inn Bed & Breakfast
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is SAR 728
SAR 814 total
includes taxes & fees
25 Nov - 26 Nov
Brook Farm Inn
Econo Lodge Lee - Great Barrington
Exterior

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (578)
"We were looking for a place not too expensive to just spend the night. This place fit the bill; clean and comfy. Bathroom needed some work and the floors were quite slippery, just coming in from the bad weather. Nothing a few scatter rugs and bathmat could fix. Bed was comfortable and a nice little dining table for 2 near the window. We'd stay there again."
The price is SAR 225
SAR 252 total
includes taxes & fees
24 Nov - 25 Nov
Econo Lodge Lee - Great Barrington
East Rock Inn
Front of property

East Rock Inn

2.0 star property
9.2 out of 10, Wonderful, (12)
"Love this motel. Visit the area monthly, this was my 5th visit at East Rock, every time has been perfect."
The price is SAR 416
SAR 464 total
includes taxes & fees
25 Nov - 26 Nov
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 traveler data. Other good choices for your trip to the area are Red Roof Inn PLUS+ West Springfield and Quality Inn West Springfield. 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 Pyramid Lake and Jacob's Pillow 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.