Find hotels in Chester, MA from ₩94,864
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Check prices for these dates
Tonight
Sep 1 - Sep 2Tomorrow
Sep 2 - Sep 3This weekend
Sep 4 - Sep 6Next weekend
Sep 11 - Sep 13Our top choices for Chester hotels
1. D. Hotel Suites & Spa
D. Hotel Suites & SpaHolyoke
Kerri
₩166,348
₩194,646 total
includes taxes & fees
Sep 14 - Sep 15
2. Best Western Springfield West Inn
Best Western Springfield West InnWest Springfield
Luz
₩139,482
₩159,636 total
includes taxes & fees
Sep 7 - Sep 8
3. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
₩149,957
₩167,502 total
includes taxes & fees
Sep 21 - Sep 22
4. Hampton Inn Westfield
Hampton Inn WestfieldWestfield
Mykola
₩166,232
₩185,681 total
includes taxes & fees
Sep 8 - Sep 9
5. Hotel Northampton
Hotel NorthamptonNorthampton
steven
₩203,089
₩226,844 total
includes taxes & fees
Sep 22 - Sep 23
6. Tru by Hilton Chicopee Springfield
Tru by Hilton Chicopee SpringfieldChicopee
Leon
₩167,093
₩189,567 total
includes taxes & fees
Sep 7 - Sep 8
7. Hampton Inn West Springfield
Hampton Inn West SpringfieldWest Springfield
Matthew
₩134,303
₩153,710 total
includes taxes & fees
Sep 6 - Sep 7
8. The Yankee Inn
The Yankee InnLenox
Karen
₩118,228
₩132,061 total
includes taxes & fees
Sep 28 - Sep 29
9. La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MAMetro Center
Sophoeun
₩161,582
₩183,314 total
includes taxes & fees
Sep 7 - Sep 8
10. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
BJORN
₩170,666
₩190,637 total
includes taxes & fees
Sep 20 - Sep 21
11. Quality Inn Westfield - Springfield
Quality Inn Westfield - SpringfieldWestfield
Thomas
₩145,308
₩162,309 total
includes taxes & fees
Sep 29 - Sep 30
12. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Prasanna
₩133,439
₩149,051 total
includes taxes & fees
Sep 15 - Sep 16
13. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
James
₩174,369
₩194,770 total
includes taxes & fees
Sep 23 - Sep 24
14. River Valley Inn
River Valley InnWest Hatfield
Michael
₩126,708
₩141,532 total
includes taxes & fees
Sep 7 - Sep 8
15. Homewood Suites by Hilton Holyoke-Springfield/North
Homewood Suites by Hilton Holyoke-Springfield/NorthHolyoke
Andrew
₩201,078
₩224,605 total
includes taxes & fees
Sep 10 - Sep 11
16. Fairfield Inn & Suites Springfield Northampton/Amherst
Fairfield Inn & Suites Springfield Northampton/AmherstNorthampton
rob
₩208,080
₩232,424 total
includes taxes & fees
Sep 20 - Sep 21
17. The Ellery
The ElleryNorthampton
Holly
₩204,620
₩228,560 total
includes taxes & fees
Sep 22 - Sep 23
18. Comfort Inn & Suites West Springfield
Comfort Inn & Suites West SpringfieldWest Springfield
Heriberto
₩167,920
₩192,175 total
includes taxes & fees
Sep 14 - Sep 15
19. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
₩109,944
₩153,359 total
includes taxes & fees
Oct 1 - Oct 2
20. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Debra
₩173,685
₩194,008 total
includes taxes & fees
Sep 15 - Sep 16
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.
Learn more about Chester
Experience the hiking, camping, and waterfalls in Chester!
See all hotels in Chester
Photo by Chris Addams
Top Chester Hotel Reviews
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Perfect stay"
Berkshire Mountain Lodge
10/10 Excellent
"Enjoyed my stay! Spacious rooms, clean, quiet, surrounded by nature, free custom coffee ☕️ in lobby, free laundry facilities (bring your own detergent), no restaurant on-site. Pittsfield had lots of dining options nearby. I recommend the local nature trails at the Audubon Sanctuary, so beautiful 😍"
The Red Lion Inn
10/10 Excellent
"The Red Lion Inn is always charming and comfortable!"
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
8/10 Good
"The room was very quiet"
D. Hotel Suites & Spa
10/10 Excellent
"My room was clean, spacious and comfortable. Breakfast was yummy."
La Quinta Inn & Suites by Wyndham Springfield MA
10/10 Excellent
"👌"
Candlewood Suites West Springfield by IHG
10/10 Excellent
"The staff that helped me check in was super helpful"
Hotel Northampton
10/10 Excellent
"Lovely, central hotel. Highly recommend."
FairBridge Inn Express
10/10 Excellent
"It was very nice and everyone was extremely helpful"
More cheap stays in Chester
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
₩84,928
₩94,864 total
Sep 6 - Sep 7
includes taxes & fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
₩118,228
₩132,061 total
Sep 28 - Sep 29
includes taxes & fees
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
₩126,708
₩145,016 total
Sep 28 - Sep 29
includes taxes & fees
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street West Springfield MA
₩126,764
₩145,082 total
Sep 10 - Sep 11
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
₩173,685
₩194,008 total
Sep 13 - Sep 14
includes taxes & fees
9.2/10 Wonderful! (181 reviews)
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
₩180,181
₩201,263 total
Sep 27 - Sep 28
includes taxes & fees
7.2/10 Good! (1,006 reviews)
