Chester Hotels from S$89
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14 Aug - 16 AugOur top choices for Chester hotels
2. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Jeanne
S$146
includes taxes & fees
31 Aug - 1 Sept
3. Berkshire Lake Lodge
Berkshire Lake LodgeLee
Rita
S$229
includes taxes & fees
2 Sept - 3 Sept
5. Hampton Inn Westfield
Hampton Inn WestfieldWestfield
Karen
S$161
includes taxes & fees
1 Sept - 2 Sept
6. Quality Inn Westfield - Springfield
Quality Inn Westfield - SpringfieldWestfield
Christopher J.
S$137
includes taxes & fees
31 Aug - 1 Sept
7. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
S$163
includes taxes & fees
31 Aug - 1 Sept
8. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
James
S$193
includes taxes & fees
7 Sept - 8 Sept
10. Fairfield Inn & Suites Springfield Holyoke
Fairfield Inn & Suites Springfield HolyokeHolyoke
Michael
S$169
includes taxes & fees
23 Aug - 24 Aug
11. River Valley Inn
River Valley InnWest Hatfield
Vidita
S$126
includes taxes & fees
6 Sept - 7 Sept
13. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Courtney
S$188
includes taxes & fees
7 Sept - 8 Sept
14. The Red Lion Inn
The Red Lion InnStockbridge
Merideth
S$310
includes taxes & fees
7 Sept - 8 Sept
15. Berkshires Untold
Berkshires UntoldLenox
Ivana
S$186
includes taxes & fees
7 Sept - 8 Sept
16. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
Kimberly
S$204
includes taxes & fees
7 Sept - 8 Sept
17. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Joseph
S$182
includes taxes & fees
30 Aug - 31 Aug
18. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
Luciane
S$113
includes taxes & fees
31 Aug - 1 Sept
19. Hampton Inn West Springfield
Hampton Inn West SpringfieldWest Springfield
Benny
S$161
includes taxes & fees
9 Aug - 10 Aug
20. D. Hotel Suites & Spa
D. Hotel Suites & SpaHolyoke
Smittie
S$182
includes taxes & fees
30 Aug - 31 Aug
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.
Learn more about Chester
Experience the hiking, camping and riverfront in Chester!
See all hotels in Chester
Photo by Chris Addams
Top Chester Hotel Reviews
D. Hotel Suites & Spa
8/10 Good
"Wonderful breakfast"
Hampton Inn West Springfield
8/10 Good
"Quick check in. Room was ok . A bit dated. Comfortable bed and good shower. Breakfast was good."
The Red Lion Inn
8/10 Good
"Property is aging and needs attention. Still a nice place to stay."
Blue A Modern Hotel, an Ascend Collection Hotel
10/10 Excellent
"Room was bright and new. Massage chair was next level comfort. Ever fixture had an interesting flair of modern convenience. That goes for the lobby which has a wider than normal array of snacks and adult drinks. and Staff was exceptionally friendly and helpful. Cookies and pastry by the coffee station but lots of food choices available nearby. Tucked well off the busy crossroads in the area make it like an oasis, but at the same time close to anywhere in the western mass area. Competitive price point."
Berkshire Mountain Lodge
10/10 Excellent
"Itโs low key and chill. I loke that a lot. Great staff."
Berkshires Untold
10/10 Excellent
"We loved the hotel. Outside area was great. Need to upgrade the cushions"
The Yankee Inn
10/10 Excellent
"Last minute reservations and we will return next year. Room, facilities, breakfast, and pool excellent."
Quality Inn & Suites Northampton - Amherst
8/10 Good
"Great, attentive staff. Awesome breakfast! Good rooms, great location, decent exercise room. Thank you!"
Tru by Hilton Chicopee Springfield
8/10 Good
"Jonathan at the front desk was super helpful and very accommodating to my families needs."
More cheap stays in Chester
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
S$89
12 Aug - 13 Aug
includes taxes & fees
5.4/10 (864 reviews)
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
S$130
2 Sept - 3 Sept
includes taxes & fees
Red Roof Inn PLUS+ West Springfield
1254 Riverdale Street West Springfield MA
S$148
18 Aug - 19 Aug
includes taxes & fees
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
S$177
18 Aug - 19 Aug
includes taxes & fees
7.2/10 Good! (1,006 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
S$188
7 Sept - 8 Sept
includes taxes & fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
S$228
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
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