Chester Hotels from S$89
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21 Sept - 22 SeptTomorrow
22 Sept - 23 SeptThis weekend
25 Sept - 27 SeptNext weekend
2 Oct - 4 OctOur top choices for Chester hotels
2. The Yankee Inn
The Yankee InnLenox
William
S$167
includes taxes & fees
28 Sept - 29 Sept
3. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Wendy
S$156
includes taxes & fees
19 Oct - 20 Oct
4. Berkshire Lake Lodge
Berkshire Lake LodgeLee
mike
S$210
includes taxes & fees
23 Sept - 24 Sept
5. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
Ann M
S$182
includes taxes & fees
28 Sept - 29 Sept
6. Hampton Inn Westfield
Hampton Inn WestfieldWestfield
Mykola
S$175
includes taxes & fees
7 Oct - 8 Oct
7. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
COLLEEN
S$113
includes taxes & fees
23 Sept - 24 Sept
8. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Susan
S$168
includes taxes & fees
20 Oct - 21 Oct
9. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Joe
S$151
includes taxes & fees
18 Oct - 19 Oct
10. Quality Inn Westfield - Springfield
Quality Inn Westfield - SpringfieldWestfield
Thomas
S$139
includes taxes & fees
18 Oct - 19 Oct
11. Hotel Northampton
Hotel NorthamptonNorthampton
zane
S$176
includes taxes & fees
23 Sept - 24 Sept
12. Monument Mountain Motel
Monument Mountain MotelGreat Barrington
Victor
S$110
includes taxes & fees
23 Sept - 24 Sept
13. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Larry
S$177
includes taxes & fees
29 Sept - 30 Sept
14. D. Hotel Suites & Spa
D. Hotel Suites & SpaHolyoke
Karen
S$182
includes taxes & fees
28 Sept - 29 Sept
15. Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great BarringtonLee
Anna
S$99
includes taxes & fees
28 Sept - 29 Sept
16. River Valley Inn
River Valley InnWest Hatfield
Michael
S$129
includes taxes & fees
23 Sept - 24 Sept
18. Berkshires Untold
Berkshires UntoldLenox
Drue
S$199
includes taxes & fees
28 Sept - 29 Sept
19. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
Maria Dulce
S$190
includes taxes & fees
19 Oct - 20 Oct
20. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
Tracy
S$202
includes taxes & fees
27 Sept - 28 Sept
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 theatre in Chester!
See all hotels in Chester
Photo by Chris Addams
Top Chester Hotel Reviews
D. Hotel Suites & Spa
10/10 Excellent
"Very convenient to Northampton, very clean and a beautiful property."
Berkshires Untold
8/10 Good
"Liked he cleanliness. Room was very cold and no heat was available."
The Yankee Inn
10/10 Excellent
"The room was spacious, clean and comfortable. I will definitely stay there again."
Hotel Northampton
8/10 Good
"Nice place"
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
10/10 Excellent
"The room was clean and perfect when we arrived! The pool area was a big hit with my boys and the breakfast the next morning was amazing!"
Riverdale Inn
8/10 Good
"Nice rooms, fridge available, comfy beds and decent showers. Only problem is no elevator for 2nd floor. And heavy doors to go through. Friendly helpful staff. Decent price. Right on the P20 bus line. Lots of restaurants in the area and Holyoke Mall is like a 5-10 min bus ride from the hotel."
La Quinta Inn & Suites by Wyndham Springfield MA
10/10 Excellent
"It was great. One staff had an attitude but overall nice place to stay."
Blue A Modern Hotel, an Ascend Collection Hotel
10/10 Excellent
"This was a great stay and the high tech massage chair was the cherry on top!"
The Red Lion Inn
10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
More cheap stays in Chester
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
S$89
5 Oct - 6 Oct
includes taxes & fees
Quality Inn West Springfield
1150 Riverdale St West Springfield MA
S$133
18 Oct - 19 Oct
includes taxes & fees
7.2/10 Good! (1,009 reviews)
Blue A Modern Hotel, an Ascend Collection Hotel
1080 Riverdale St West Springfield MA
S$148
18 Oct - 19 Oct
includes taxes & fees
9.2/10 Wonderful! (336 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
S$167
28 Sept - 29 Sept
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
S$168
20 Oct - 21 Oct
includes taxes & fees
9.4/10 Exceptional! (216 reviews)
Quality Inn & Suites Northampton - Amherst
117 Conz St Northampton MA
S$174
12 Oct - 13 Oct
includes taxes & fees
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