Find hotels in Chester, MA from ￥12,052

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Check prices for these dates

Tonight
Jan 27 - Jan 28
Tomorrow
Jan 28 - Jan 29
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

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Our top choices for Chester hotels

Room (Louis XIV) | Individually decorated, individually furnished, iron/ironing board

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (425 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is ￥15,746
￥17,864 total
includes taxes & fees
Jan 28 - Jan 29
Naomi's Inn Bed & Breakfast
Individually decorated, individually furnished, desk, laptop workspace

Pilgrim Inn

Pilgrim Inn
2.5 star property
Lee
5.8 out of 10, (332 reviews)
"Was horrible. Unsafe and scarey"
United States
Sharon
The price is ￥12,365
￥13,812 total
includes taxes & fees
Jan 28 - Jan 29
Pilgrim Inn
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (655 reviews)
"The room was clean and the service adequate"
United States
David
The price is ￥10,911
￥12,188 total
includes taxes & fees
Feb 13 - Feb 14
Econo Lodge Lee - Great Barrington
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Suite, Private Bathroom (RedBird Suite) | View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ￥47,773
￥57,792 total
includes taxes & fees
Feb 16 - Feb 17
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811 reviews)
"Room spotless and staff helpful."
United States
William
The price is ￥12,365
￥13,812 total
includes taxes & fees
Feb 10 - Feb 11
FairBridge Inn Express
Standard Double Room, 2 Double Beds, Non Smoking | Premium bedding, desk, iron/ironing board, rollaway beds

Quality Inn Chicopee - Springfield

Quality Inn Chicopee - Springfield
2.5 star property
Chicopee
6.4 out of 10, (845 reviews)
"Breakfast was convenient, loved coffee in the lobby and staff very friendly. "
United States
Julia
The price is ￥15,283
￥17,338 total
includes taxes & fees
Feb 1 - Feb 2
Quality Inn Chicopee - Springfield
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is ￥14,665
￥16,381 total
includes taxes & fees
Jan 28 - Jan 29
Sunset Inn
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Terrace/patio

Residence Inn Springfield Chicopee

Residence Inn Springfield Chicopee
3.0 star property
Chicopee
9.2 out of 10, Wonderful, (481 reviews)
"The hotel staff were very friendly and the hotel was clean"
United States
Samantha
The price is ￥22,175
￥25,157 total
includes taxes & fees
Feb 2 - Feb 3
Residence Inn Springfield Chicopee
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, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is ￥15,128
￥16,898 total
includes taxes & fees
Jan 30 - Jan 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is ￥36,864
￥43,236 total
includes taxes & fees
Feb 1 - Feb 2
The Inn at Stockbridge
Exterior

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.6 out of 10, Excellent, (104 reviews)
"Clean room, staff were excellent, and provided everything I needed. Its a cozy, relaxed place with minimal intrusion. "
United States
Steven
The price is ￥15,283
￥17,071 total
includes taxes & fees
Jan 28 - Jan 29
River Valley Inn
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ￥22,229
￥26,071 total
includes taxes & fees
Jan 29 - Jan 30
Lakehouse Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ￥12,743
￥14,234 total
includes taxes & fees
Feb 15 - Feb 16
Berkshire Inn
Lobby

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123 reviews)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is ￥13,739
￥15,346 total
includes taxes & fees
Jan 28 - Jan 29
Elm Motel
Balcony

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (354 reviews)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ￥14,511
￥16,209 total
includes taxes & fees
Feb 15 - Feb 16
The Central Downtown Inn & Suites
Front of property

Becket Motel

Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
"Comfortable stay "
United States
Paul
The price is ￥13,208
￥19,927 total
includes taxes & fees
Jan 28 - Jan 29
Becket Motel
Indoor pool

Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,002 reviews)
"Clean comfortable rooms, great breakfast, very nice staff"
United States
Edward
The price is ￥16,329
￥18,526 total
includes taxes & fees
Feb 8 - Feb 9
Hampton Inn Chicopee/Springfield
Exterior

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
Metro Center
8.0 out of 10, Very Good, (1,308 reviews)
"Breakfast "
United States
Twain
The price is ￥17,058
￥19,352 total
includes taxes & fees
Jan 29 - Jan 30
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 during your trip to Chester. Wander the lakeside and forest in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping, and riverfront in Chester!

See all hotels in Chester
An amazing keystone arch bridge!
Photo by Chris Addams
Open Photo by Chris Addams

Top Chester Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Everything good"
Herika 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is ￥10,531 per night from Feb 1 to Feb 2
￥10,531
￥12,052 total
Feb 1 - Feb 2
includes taxes & fees
5.8/10 (1,001 reviews)

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 Berkshire Mountain Lodge and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Chester.
What are some of the best vacation rentals in Chester?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental outside of Chester offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. 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 Hiram H. Fox Wildlife Management Area and Pyramid Lake 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.

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