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Our top choices for Chester hotels

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 AU$558
includes taxes & fees
15 Feb - 16 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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 AU$133
includes taxes & fees
25 Jan - 26 Jan
Pilgrim Inn

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 AU$172
includes taxes & fees
21 Jan - 22 Jan
Naomi's Inn Bed & Breakfast

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

Quality Inn Chicopee - Springfield

Quality Inn Chicopee - Springfield
2.5 star property
Chicopee
6.4 out of 10, (843 reviews)
"Breakfast was convenient, loved coffee in the lobby and staff very friendly. "
United States
Julia
The price is AU$167
includes taxes & fees
27 Jan - 28 Jan
Quality Inn Chicopee - Springfield

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (654 reviews)
"The room was clean and the service adequate"
United States
David
The price is AU$112
includes taxes & fees
27 Jan - 28 Jan
Econo Lodge Lee - Great Barrington

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 AU$133
includes taxes & fees
3 Feb - 4 Feb
FairBridge Inn Express

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 AU$243
includes taxes & fees
27 Jan - 28 Jan
Residence Inn Springfield Chicopee

River Valley Inn

River Valley Inn
2.0 star property
West Hatfield
8.4 out of 10, Very good, (103 reviews)
"Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!"
United States
Deb
The price is AU$165
includes taxes & fees
22 Jan - 23 Jan
River Valley 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 AU$158
includes taxes & fees
21 Jan - 22 Jan
Sunset Inn

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

Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean comfortable rooms, great breakfast, very nice staff"
United States
Edward
The price is AU$179
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn Chicopee/Springfield

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 AU$149
includes taxes & fees
21 Jan - 22 Jan
Elm Motel

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, (1,006 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is AU$163
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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 AU$227
includes taxes & fees
29 Jan - 30 Jan
Lakehouse 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 AU$142
includes taxes & fees
22 Jan - 23 Jan
Berkshire Inn

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (60 reviews)
"The property is very clean and pet friendly. The staff were very friendly and professional. I will definitely stay here again."
United States
Diana
The price is AU$248
includes taxes & fees
3 Feb - 4 Feb
TownePlace Suites by Marriott Hadley Amherst

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 AU$156
includes taxes & fees
8 Feb - 9 Feb
The Central Downtown Inn & Suites

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AU$316
includes taxes & fees
26 Jan - 27 Jan
Harbour House Inn

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
West Springfield
9.4 out of 10, Exceptional, (127 reviews)
"Clean, cool rooms. Staff was very welcoming & professional."
United States
David
The price is AU$202
includes taxes & fees
9 Feb - 10 Feb
Blue – A Modern Hotel, an Ascend Collection Hotel
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

Learn more about Chester

Experience the hiking, camping and riverfront in Chester!

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

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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 traveller data. Other good choices for your visit 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 holiday rentals that Chester has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Chester offers a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes, the majority of room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
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, theatres and monuments. In Chester, there are 2 hotels and other accommodation options to choose from. Find out more about Chester.
What is there to see in Chester?
A favourite place to visit is Chester Town Hall. You'll also find Pyramid Lake and Blandford Ski Area in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.

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