Cheshire hotels from HK$544
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11 Aug - 12 AugTomorrow
12 Aug - 13 AugThis weekend
14 Aug - 16 AugNext weekend
21 Aug - 23 AugOur top choices for Cheshire hotels
1. Harbour House Inn
Harbour House InnCheshire
Gregory
HK$1,990
HK$2,104 total
includes taxes & fees
20 Aug - 21 Aug
2. The Springs Motel
The Springs MotelNew Ashford
Shakeila
HK$1,227
HK$1,346 total
includes taxes & fees
23 Aug - 24 Aug
3. The Revival House
The Revival HouseAdams
James
HK$1,299
HK$1,451 total
includes taxes & fees
16 Aug - 17 Aug
4. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
HK$894
HK$999 total
includes taxes & fees
30 Aug - 31 Aug
5. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
William
HK$1,091
HK$1,219 total
includes taxes & fees
9 Sept - 10 Sept
6. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Brooks
HK$758
HK$933 total
includes taxes & fees
2 Sept - 3 Sept
7. Berkshire Valley Inn
Berkshire Valley InnWilliamstown
DM
HK$1,306
HK$1,459 total
includes taxes & fees
19 Aug - 20 Aug
8. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
DAVID
HK$487
HK$544 total
includes taxes & fees
13 Aug - 14 Aug
9. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Richard
HK$812
HK$907 total
includes taxes & fees
16 Aug - 17 Aug
10. The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art HotelAdams
Jenna
HK$1,569
HK$1,753 total
includes taxes & fees
12 Aug - 13 Aug
11. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
David
HK$996
HK$1,113 total
includes taxes & fees
23 Aug - 24 Aug
12. The Yankee Inn
The Yankee InnLenox
Larry
HK$1,294
HK$1,446 total
includes taxes & fees
7 Sept - 8 Sept
13. Berkshire Inn
Berkshire InnPittsfield
christopher
HK$706
HK$789 total
includes taxes & fees
12 Aug - 13 Aug
14. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
hui
HK$1,648
HK$1,840 total
includes taxes & fees
10 Sept - 11 Sept
15. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Christine
HK$981
HK$1,095 total
includes taxes & fees
8 Sept - 9 Sept
16. Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
Sandy
HK$1,247
HK$1,393 total
includes taxes & fees
30 Aug - 31 Aug
17. Hotel On North
Hotel On NorthPittsfield
Dragana
HK$1,404
HK$1,569 total
includes taxes & fees
7 Sept - 8 Sept
18. Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
Donna
HK$784
HK$876 total
includes taxes & fees
12 Aug - 13 Aug
19. Blue Vista Motor Lodge
Blue Vista Motor LodgeNorth Adams
Frederic
HK$1,932
HK$2,043 total
includes taxes & fees
12 Aug - 13 Aug
20. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Jeremy
HK$692
HK$813 total
includes taxes & fees
8 Sept - 9 Sept
Stay near popular Cheshire attractions
St Mary's of the Assumption Church
10.0/10 (1 review)
This historic Catholic parish has served Cheshire's community since 1879, offering a serene space for reflection. Visit during religious holidays to experience special services in its traditional architectural setting.
Learn more about Cheshire
Top Cheshire Hotel Reviews
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
10/10 Excellent
"A clean pleasant place to stay"
The Red Lion Inn
10/10 Excellent
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."
The Yankee Inn
8/10 Good
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Quality Inn Lee - Lenox South
8/10 Good
"Very nice stay"
Berkshires Untold
8/10 Good
"Very clean-great beds!"
Berkshire Mountain Lodge
10/10 Excellent
"Good location, nice room, easy access"
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Perfect spot for a quick unwind. Very cozy, well appointed Villa. Porch was very enjoyable - able to sit out there through rain storm !"
Jiminy Peak Mountain Resort
10/10 Excellent
"Quiet and serene. Great weekend escape!"
The Williams Inn
10/10 Excellent
"Go Ephs!"
More cheap stays in Cheshire
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
HK$487
HK$544 total
13 Aug - 14 Aug
includes taxes & fees
5.4/10 (867 reviews)
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
HK$620
HK$692 total
7 Sept - 8 Sept
includes taxes & fees
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
HK$794
HK$886 total
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very good! (1,011 reviews)
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
HK$894
HK$999 total
30 Aug - 31 Aug
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
HK$996
HK$1,113 total
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (156 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
HK$1,294
HK$1,446 total
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
