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Find hotels in Chester, MA from ฿1,543

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Check prices for these dates

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6 Jan - 7 Jan
Tomorrow
7 Jan - 8 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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Our top choices for Chester hotels

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, (840)
"Breakfast was convenient, loved coffee in the lobby and staff very friendly. "
United States
Julia
The price is ฿2,954
฿3,351 total
includes taxes & fees
1 Feb - 2 Feb
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, (478)
"The rooms were clean, large, and comfortable! We loved our stay here and will definitely be returning. All of the staff were also amazing and the hot breakfast is a great plus. Convenient location with lots of parking. "
United States
Samantha
The price is ฿4,765
฿5,405 total
includes taxes & fees
15 Jan - 16 Jan
Residence Inn Springfield Chicopee
Indoor pool
Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1003)
"Clean comfortable rooms, great breakfast, very nice staff"
United States
Edward
The price is ฿3,313
฿3,758 total
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn Chicopee/Springfield
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)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is ฿3,163
฿3,588 total
includes taxes & fees
14 Jan - 15 Jan
Naomi's Inn Bed & Breakfast
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)
"Room spotless and staff helpful."
United States
William
The price is ฿2,508
฿2,802 total
includes taxes & fees
2 Feb - 3 Feb
FairBridge Inn Express
Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"Nice place for a weekend away."
United States
Gregory
The price is ฿6,733
฿7,117 total
includes taxes & fees
7 Jan - 8 Jan
Harbour House Inn
Exterior
Homewood Suites by Hilton Holyoke-Springfield/North

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, (1000)
"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 ฿3,826
฿4,274 total
includes taxes & fees
13 Jan - 14 Jan
Homewood Suites by Hilton Holyoke-Springfield/North
Lobby
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield
2.5 star property
Chicopee
9.0 out of 10, Wonderful, (1005)
"Everything was perfect: clean room, great breakfast, courteous staff!"
United States
Tiffany
The price is ฿2,799
฿3,175 total
includes taxes & fees
19 Jan - 20 Jan
Tru by Hilton Chicopee Springfield
Property amenity
Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke

Fairfield Inn & Suites Springfield Holyoke
2.5 star property
Holyoke
9.2 out of 10, Wonderful, (601)
"Room was very clean, the breakfast was delicious!"
United States
William
The price is ฿3,695
฿4,128 total
includes taxes & fees
8 Jan - 9 Jan
Fairfield Inn & Suites Springfield Holyoke
Property amenity
TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst

TownePlace Suites by Marriott Hadley Amherst
3.0 star property
Hadley
9.6 out of 10, Exceptional, (60)
"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 ฿4,657
฿5,202 total
includes taxes & fees
13 Jan - 14 Jan
TownePlace Suites by Marriott Hadley Amherst
Reception
Elm Motel

Elm Motel

Elm Motel
2.0 star property
Westfield
7.2 out of 10, Good, (123)
"Very clean, lacking bathroom and bathroom storage. Good price."
United States
Daniel
The price is ฿2,787
฿3,113 total
includes taxes & fees
23 Jan - 24 Jan
Elm Motel
Front of property
Gedney Farm

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (133)
"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 ฿5,809
฿6,372 total
includes taxes & fees
8 Jan - 9 Jan
Gedney Farm
Microwave, oven, stovetop, dishwasher
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, (351)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ฿2,944
฿3,288 total
includes taxes & fees
12 Jan - 13 Jan
The Central Downtown Inn & Suites
Exterior
Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area

Hampton Inn Hadley-Amherst Area
2.5 star property
Hadley
9.0 out of 10, Wonderful, (967)
"Staff was very friendly, room very clean"
United States
Christine
The price is ฿4,033
฿4,504 total
includes taxes & fees
1 Feb - 2 Feb
Hampton Inn Hadley-Amherst Area
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
East Rock Inn

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is ฿4,080
฿4,557 total
includes taxes & fees
19 Jan - 20 Jan
East Rock Inn
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

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)
"Excellent location!!"
United States
Abdul Samad
The price is ฿2,349
฿2,624 total
includes taxes & fees
7 Jan - 8 Jan
Travelodge by Wyndham Great Barrington Berkshires
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)
"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 ฿2,693
฿3,008 total
includes taxes & fees
19 Jan - 20 Jan
Berkshire Inn
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished
The Old Inn On The Green

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)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is ฿9,551
฿11,525 total
includes taxes & fees
12 Jan - 13 Jan
The Old Inn On The Green
Terrace/patio
Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst

Homewood Suites by Hilton Hadley Amherst
3.0 star property
Hadley
9.4 out of 10, Exceptional, (723)
"great location and huge room, very nice hotel suite!"
United States
Lihong
The price is ฿4,408
฿4,924 total
includes taxes & fees
1 Feb - 2 Feb
Homewood Suites by Hilton Hadley Amherst
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"Perfect for pets "
United States
Maria
The price is ฿3,445
฿3,848 total
includes taxes & fees
12 Jan - 13 Jan
The Little Lion
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 on your trip to Chester. Wander the lakeside and forests in this relaxing area.
See properties

Learn more about Chester

Experience the hiking, camping and theatre 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

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

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

10/10 Excellent
"Pool was excellent ."
Robert 2-night trip
Posted 3 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

More cheap stays in Chester

Riverdale Inn

Riverdale Inn

1500 Riverdale Street West Springfield MA
The price is ฿2,297 per night from 8 Jan to 9 Jan
฿2,297
฿2,629 total
8 Jan - 9 Jan
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 traveller data. Other good choices for your visit to the area are The Red Lion Inn and Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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, 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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