Photo by Elizabeth Massa Peroulakis

Find hotels in Chester, MA from AED 228

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Check prices for these dates

Tonight
23 Apr - 24 Apr
Tomorrow
24 Apr - 25 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

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Compare 805 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Becket Motel
Front of property

Becket Motel

2.5 star property
6.6 out of 10, (55)
"I liked how there was walking trails and shopping near by. "
The price is AED 349
AED 513 total
includes taxes & fees
24 Apr - 25 Apr
Becket Motel
Pilgrim Inn
Individually decorated, individually furnished, desk, laptop workspace

Pilgrim Inn

2.5 star property
5.8 out of 10, (305)
"Very comfortable and in a convenient location"
The price is AED 253
AED 283 total
includes taxes & fees
4 May - 5 May
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Super clean and friendly My only issue was the cable tv had no news channels. MSNBC or CNN. "
The price is AED 330
AED 369 total
includes taxes & fees
18 May - 19 May
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (380)
"The room was clean and perfect for our stay."
The price is AED 331
AED 369 total
includes taxes & fees
29 Apr - 30 Apr
Sunset Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 881
AED 985 total
includes taxes & fees
25 Apr - 26 Apr
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (587)
"While the gentleman at the front desk can be a bit cold, the women that work at the property are very pleasant. They were super accommodating and did a nice job cleaning the room during our stay. The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
The price is AED 228
AED 255 total
includes taxes & fees
29 Apr - 30 Apr
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (124)
"Very enjoyable comfortable stay"
The price is AED 915
AED 1,022 total
includes taxes & fees
24 Apr - 25 Apr
Devonfield Inn B&B
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, (1001)
"Nice hotel, very helpful staff, and very nice and peaceful lake view from my room."
The price is AED 340
AED 380 total
includes taxes & fees
29 Apr - 30 Apr
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (622)
"We always have a great time, have stayed several times. Try and get a top unit if you can because we went several nights of no sleep due to running playing children above us."
The price is AED 393
AED 491 total
includes taxes & fees
29 Apr - 30 Apr
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Quality Inn Westfield - Springfield
Lobby

Quality Inn Westfield - Springfield

2.5 star property
7.2 out of 10, Good, (773)
"Minutes from the highway. "
The price is AED 343
AED 384 total
includes taxes & fees
11 May - 12 May
Quality Inn Westfield - Springfield
Hampton Inn Westfield
Room, 2 Queen Beds, Refrigerator | Premium bedding, desk, laptop workspace, blackout drapes

Hampton Inn Westfield

2.5 star property
8.4 out of 10, Very Good, (730)
"Nice room but limited housekeeping"
The price is AED 496
AED 555 total
includes taxes & fees
30 Apr - 1 May
Hampton Inn Westfield
Gateways Inn & Restaurant
Room (King Room) | Iron/ironing board, free WiFi, bed sheets

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (186)
"Always a good place to stay. And so convenient to walk to all the restaurants and shops in town."
The price is AED 633
AED 739 total
includes taxes & fees
29 Apr - 30 Apr
Gateways Inn & Restaurant
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, (438)
"Lovely location!"
The price is AED 279
AED 312 total
includes taxes & fees
1 May - 2 May
The Constance, The Whitlock, & The Dewey By The Lenox Collection
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AED 1,441
AED 1,610 total
includes taxes & fees
24 Apr - 25 Apr
33 Main
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...
The price is AED 601
AED 741 total
includes taxes & fees
6 May - 7 May
Whistler's Inn Bed & Breakfast
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"We had a wonderful wknd in Lenox. The Cornell Inn was very accommodating and everyone was extremely friendly, welcoming and helpful. We had emailed beforehand about dietary restrictions and they were helpful and gave great recommendations for places that could accommodate us. Their breakfasts are excellent and filling. That starts your day off so nicely. The rooms were comfortable and roomy. Although the room was a bit dated -it was cozy and suited us perfectly. It was a great location...
The price is AED 455
AED 652 total
includes taxes & fees
24 Apr - 25 Apr
The Cornell Inn, Lenox & The Berkshires
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (553)
"Clean , Nice staff , quiet "
The price is AED 621
AED 693 total
includes taxes & fees
27 Apr - 28 Apr
Courtyard by Marriott Lenox Berkshires
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"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 780
AED 871 total
includes taxes & fees
27 Apr - 28 Apr
Brook Farm Inn
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (119)
"Beautiful and rustic, less than 15 minutes to Butternut and Great Barrington."
The price is AED 791
AED 989 total
includes taxes & fees
24 Apr - 25 Apr
Gedney Farm
Berkshires Untold
Lobby

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (567)
"It was an older motel, remodeled recently. It was a mini-vacation, a great place and great food."
The price is AED 392
AED 438 total
includes taxes & fees
6 May - 7 May
Berkshires Untold
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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Learn more about Chester

Experience the hiking, camping, and monuments in Chester!

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

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 Berkshires Untold and Quality Inn West Springfield. See all available top hotels, or 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.