
Search Chester hotels
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Chester
Apartment
Family friendly
Check prices for these dates
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 ChesterwoodStockbridge
9.2 out of 10, Wonderful, (110 reviews)
The price is AU$558
includes taxes & fees
15 Feb - 16 Feb

Pilgrim Inn
Pilgrim InnLee
5.8 out of 10, (332 reviews)
The price is AU$133
includes taxes & fees
25 Jan - 26 Jan

Naomi's Inn Bed & Breakfast
Naomi's Inn Bed & BreakfastLiberty Heights
9.0 out of 10, Wonderful, (424 reviews)
The price is AU$172
includes taxes & fees
21 Jan - 22 Jan

Quality Inn Chicopee - Springfield
Quality Inn Chicopee - SpringfieldChicopee
6.4 out of 10, (843 reviews)
The price is AU$167
includes taxes & fees
27 Jan - 28 Jan

Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great BarringtonLee
6.4 out of 10, (654 reviews)
The price is AU$112
includes taxes & fees
27 Jan - 28 Jan

FairBridge Inn Express
FairBridge Inn ExpressPittsfield
5.4 out of 10, (811 reviews)
The price is AU$133
includes taxes & fees
3 Feb - 4 Feb

Residence Inn Springfield Chicopee
Residence Inn Springfield ChicopeeChicopee
9.2 out of 10, Wonderful, (480 reviews)
The price is AU$243
includes taxes & fees
27 Jan - 28 Jan

River Valley Inn
River Valley InnWest Hatfield
8.4 out of 10, Very good, (103 reviews)
The price is AU$165
includes taxes & fees
22 Jan - 23 Jan

Sunset Inn
Sunset InnLee
7.6 out of 10, Good, (411 reviews)
The price is AU$158
includes taxes & fees
21 Jan - 22 Jan

Hampton Inn Chicopee/Springfield
Hampton Inn Chicopee/SpringfieldChicopee
9.0 out of 10, Wonderful, (1,001 reviews)
The price is AU$179
includes taxes & fees
1 Feb - 2 Feb

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very good, (1,006 reviews)
The price is AU$163
includes taxes & fees
23 Jan - 24 Jan

Lakehouse Inn
Lakehouse InnLee
9.6 out of 10, Exceptional, (290 reviews)
The price is AU$227
includes taxes & fees
29 Jan - 30 Jan

Berkshire Inn
Berkshire InnPittsfield
7.8 out of 10, Good, (841 reviews)
The price is AU$142
includes taxes & fees
22 Jan - 23 Jan

TownePlace Suites by Marriott Hadley Amherst
TownePlace Suites by Marriott Hadley AmherstHadley
9.6 out of 10, Exceptional, (60 reviews)
The price is AU$248
includes taxes & fees
3 Feb - 4 Feb

The Central Downtown Inn & Suites
The Central Downtown Inn & SuitesPittsfield
8.6 out of 10, Excellent, (354 reviews)
The price is AU$156
includes taxes & fees
8 Feb - 9 Feb

Harbour House Inn
Harbour House InnCheshire
9.4 out of 10, Exceptional, (53 reviews)
The price is AU$316
includes taxes & fees
26 Jan - 27 Jan

Blue – A Modern Hotel, an Ascend Collection Hotel
Blue – A Modern Hotel, an Ascend Collection HotelWest Springfield
9.4 out of 10, Exceptional, (127 reviews)
The price is AU$202
includes taxes & fees
9 Feb - 10 Feb
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.
Save an average of 15% on thousands of hotels when you're signed in
Stay near popular Chester attractions
Learn more about Chester
Experience the hiking, camping and riverfront in Chester!

Photo by Elizabeth Massa Peroulakis
Open Photo by Elizabeth Massa Peroulakis
Top Chester Hotel Reviews
Recent Reviews in Chester

The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
More cheap accommodation in Chester

Riverdale Inn
1500 Riverdale Street West Springfield MA
The price is AU$116 per night from 25 Jan to 26 Jan
AU$116
25 Jan - 26 Jan
includes taxes & fees
5.8/10 (1,001 reviews)
Frequently asked questions
Explore a world of travel with Expedia
- Beach Hotels in Becket
- Cheap Hotels in Becket
- Hotels with Parking in Becket
- Cheap Hotels in Blandford
- Luxury Hotels in Blandford
- Ski Hotels in Blandford
- Blandford Hotels
- Chesterfield Hotels
- Cummington Hotels
- Dalton Hotels
- Easthampton Hotels
- Florence Hotels
- Holiday Homes in Goshen
- Luxury Hotels in Goshen
- Goshen Hotels
- Guest Houses in Granville
- Holiday Homes in Granville
- Cheap Hotels in Granville
- Granville Hotels
- Motels in Granville
- Cheap Hotels in Hinsdale
- Huntington Hotels
- Castles in Lee
- Lgbt Welcoming Hotels in Lee
- Lee Hotels
- Lenox Hotels
- B&B in Monterey
- Condominium Resort in Monterey
- Cheap Hotels in Monterey
- Family Hotels in Monterey
- Monterey Hotels
- Resort in Monterey
- Hotels near National Shrine of the Divine Mercy
- Northampton Hotels
- Apartments in Otis
- Caravan Parks in Otis
- Holiday Homes in Otis
- Otis Hotels
- Lodges in Otis
- Hotels near Otis Ridge
- B&B in Peru
- Holiday Homes in Peru
- Cheap Hotels in Peru
- Peru Hotels
- B&B in Russell
- Holiday Homes in Russell
- Family Hotels in Russell
- Russell Hotels
- Inns in Russell
- Motels in Russell
- Sherwood Forest Hotels
- B&B in Southampton
- Holiday Homes in Southampton
- Cheap Hotels in Southampton
- Historic Hotels in Southampton
- Luxury Hotels in Southampton
- Southampton Hotels
- Stockbridge Hotels
- Apartments in The Berkshires
- B&B in The Berkshires
- Holiday Homes in The Berkshires
- All Inclusive Hotels in The Berkshires
- Family Hotels in The Berkshires
- Pet Friendly Hotels in The Berkshires
- Spa Hotels in The Berkshires
- The Berkshires Hotels
- Resort in The Berkshires
- Hotels near The Mount
- Luxury Hotels in Tolland
- Tolland Hotels
- Tyringham Hotels
- Lodges in Tyringham
- B&B in Washington
- Washington Hotels
- Western Massachusetts Hotels
- Westfield Hotels
- Westhampton Hotels
- Cheap Hotels in Williamsburg
- Luxury Hotels in Williamsburg
- Windsor Hotels
- B&B in Worthington
- Luxury Hotels in Worthington












































































