Chester Hotels

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Our top choices for Chester hotels

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 €94
includes taxes & fees
2 Feb - 3 Feb
Quality Inn Chicopee - Springfield

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 €140
includes taxes & fees
21 Jan - 22 Jan
Residence Inn Springfield Chicopee

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 €99
includes taxes & fees
20 Jan - 21 Jan
Naomi's Inn Bed & Breakfast

Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,004 reviews)
"Clean room, courteous staff and all the amenities you could want. "
United States
Jeanann
The price is €103
includes taxes & fees
8 Feb - 9 Feb
Hampton Inn Chicopee/Springfield

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 €77
includes taxes & fees
29 Jan - 30 Jan
FairBridge Inn Express

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 €195
includes taxes & fees
29 Jan - 30 Jan
Harbour House Inn

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 €95
includes taxes & fees
30 Jan - 31 Jan
Elm Motel

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 €90
includes taxes & fees
25 Jan - 26 Jan
The Central Downtown Inn & Suites

Homewood Suites by Hilton Holyoke-Springfield/North

Homewood Suites by Hilton Holyoke-Springfield/North
3.0 star property
Holyoke
9.0 out of 10, Wonderful, (1,000 reviews)
"We absolutely love it here. My husband and I stay here a couple times a year for a getaway. The staff is always pleasant. They are renovating the hotel, but it is not affecting the stay at all. I highly recommend this hotel. I cannot wait for my next stay!"
United States
MELISSA
The price is €117
includes taxes & fees
21 Jan - 22 Jan
Homewood Suites by Hilton Holyoke-Springfield/North

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (134 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is €175
includes taxes & fees
19 Jan - 20 Jan
Gedney Farm

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is €133
includes taxes & fees
20 Jan - 21 Jan
East Rock 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 €143
includes taxes & fees
26 Jan - 27 Jan
TownePlace Suites by Marriott Hadley Amherst

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 €42
includes taxes & fees
3 Feb - 4 Feb
Pilgrim 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 €82
includes taxes & fees
21 Jan - 22 Jan
Berkshire Inn

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1,000 reviews)
"Great Breakfast and parking! "
United States
Oluwatimilehin
The price is €87
includes taxes & fees
1 Feb - 2 Feb
Tru by Hilton Chicopee Springfield

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
2.5 star property
Holyoke
9.2 out of 10, Wonderful, (606 reviews)
"Room was spotless, staff were nice. "
United States
Jose I Medina
The price is €113
includes taxes & fees
3 Feb - 4 Feb
Fairfield Inn & Suites Springfield Holyoke

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is €72
includes taxes & fees
19 Jan - 20 Jan
Travelodge by Wyndham Great Barrington Berkshires

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 €322
includes taxes & fees
15 Feb - 16 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is €316
includes taxes & fees
26 Jan - 27 Jan
The Old Inn On The Green

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)
"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 €94
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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

Top Chester Hotel Reviews

More cheap stays in Chester

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 Holiday Inn & Suites Pittsfield-Berkshires by IHG and Quality Inn West Springfield. 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 Skyline Trail 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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