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Find hotels in Chester, MA from ₩71,875

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Our top choices for Chester hotels

In-room dining
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (653 reviews)
"The room was clean and the service adequate"
United States
David
The price is ₩109,141
₩121,910 total
includes taxes & fees
Jan 25 - Jan 26
Econo Lodge Lee - Great Barrington
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

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)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ₩557,263
₩674,130 total
includes taxes & fees
Jan 25 - Jan 26
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
Chambery Inn

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
Room (Louis XIV) | Individually decorated, individually furnished, iron/ironing board
Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (424 reviews)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is ₩147,370
₩167,199 total
includes taxes & fees
Jan 14 - Jan 15
Naomi's Inn Bed & Breakfast
Individually decorated, individually furnished, desk, laptop workspace
Pilgrim Inn

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 ₩64,346
₩71,875 total
includes taxes & fees
Feb 3 - Feb 4
Pilgrim Inn
Front of property - evening/night
Devonfield Inn B&B

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
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

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 ₩116,875
₩130,549 total
includes taxes & fees
Jan 25 - Jan 26
FairBridge Inn Express
Seasonal outdoor pool
Sunset Inn

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 ₩131,320
₩146,684 total
includes taxes & fees
Jan 13 - Jan 14
Sunset Inn
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1,004 reviews)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is ₩142,993
₩159,729 total
includes taxes & fees
Jan 23 - Jan 24
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Porch
Lakehouse Inn

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 ₩210,112
₩246,429 total
includes taxes & fees
Jan 16 - Jan 17
Lakehouse Inn
Lobby
Elm Motel

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 ₩129,861
₩145,050 total
includes taxes & fees
Jan 23 - Jan 24
Elm Motel
Front of property
The Inn at Stockbridge

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 ₩383,454
₩449,742 total
includes taxes & fees
Jan 23 - Jan 24
The Inn at Stockbridge
Desk, iron/ironing board, free WiFi, bed sheets
Berkshire Inn

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 ₩125,469
₩140,148 total
includes taxes & fees
Jan 19 - Jan 20
Berkshire Inn
Balcony
The Central Downtown Inn & Suites

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 ₩137,156
₩153,206 total
includes taxes & fees
Jan 25 - Jan 26
The Central Downtown Inn & Suites
Exterior
River Valley Inn

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very Good, (102 reviews)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is ₩144,452
₩161,353 total
includes taxes & fees
Jan 13 - Jan 14
River Valley Inn
Standard Double Room, 2 Double Beds, Non Smoking | Premium bedding, desk, iron/ironing board, rollaway beds
Quality Inn Chicopee - Springfield

Quality Inn Chicopee - Springfield

Quality Inn Chicopee - Springfield
2.5 star property
Chicopee
6.4 out of 10, (842 reviews)
"Breakfast was convenient, loved coffee in the lobby and staff very friendly. "
United States
Julia
The price is ₩140,075
₩158,912 total
includes taxes & fees
Feb 2 - Feb 3
Quality Inn Chicopee - Springfield
Terrace/patio
Residence Inn Springfield Chicopee

Residence Inn Springfield Chicopee

Residence Inn Springfield Chicopee
3.0 star property
Chicopee
9.2 out of 10, Wonderful, (480 reviews)
"The hotel staff were very friendly and the hotel was clean"
United States
Samantha
The price is ₩222,004
₩251,863 total
includes taxes & fees
Jan 18 - Jan 19
Residence Inn Springfield Chicopee
Exterior
La Quinta Inn & Suites by Wyndham Springfield MA

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, (1,313 reviews)
"Eceryone was great but kudos to front desk Isha and Manager Greg who went above and beyond to make my stay enjoyable"
United States
Toni-Ann
The price is ₩161,232
₩182,917 total
includes taxes & fees
Jan 14 - Jan 15
La Quinta Inn & Suites by Wyndham Springfield MA
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ₩186,591
₩208,419 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is ₩111,439
₩124,478 total
includes taxes & fees
Jan 25 - Jan 26
Best Western Plus Berkshire Hills Inn & Suites
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
Frozen Sanderson Brook Falls in Chester
Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis

Top Chester Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"The staff are wonderful and the it is always very clean!"
Mona 3-night trip
Posted 3 days ago
The Ellery

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is ₩107,025 per night from Jan 13 to Jan 14
₩107,025
₩122,490 total
Jan 13 - Jan 14
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 Holiday Inn & Suites Pittsfield-Berkshires by IHG 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 Pyramid Lake and Skyline Trail 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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