Find hotels in Cheshire, MA from ₩92,950
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Check prices for these dates
Tonight
Sep 11 - Sep 12Tomorrow
Sep 12 - Sep 13This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Our top choices for Cheshire hotels
1. Harbour House Inn
Harbour House InnCheshire
Gregory
₩339,958
₩359,334 total
includes taxes & fees
Sep 24 - Sep 25
2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Sarah
₩127,492
₩157,109 total
includes taxes & fees
Sep 16 - Sep 17
3. The Yankee Inn
The Yankee InnLenox
Karen
₩155,440
₩173,627 total
includes taxes & fees
Sep 22 - Sep 23
4. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Christine
₩167,500
₩187,104 total
includes taxes & fees
Sep 20 - Sep 21
5. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Janis
₩118,188
₩138,918 total
includes taxes & fees
Sep 17 - Sep 18
6. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Chris
₩138,757
₩154,984 total
includes taxes & fees
Sep 14 - Sep 15
7. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
₩107,447
₩150,173 total
includes taxes & fees
Oct 1 - Oct 2
8. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
BONNIE
₩192,491
₩215,013 total
includes taxes & fees
Sep 20 - Sep 21
9. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Joe
₩141,745
₩158,329 total
includes taxes & fees
Sep 13 - Sep 14
10. Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
Donna
₩147,387
₩164,633 total
includes taxes & fees
Sep 15 - Sep 16
11. Hotel On North
Hotel On NorthPittsfield
Drew
₩179,895
₩200,943 total
includes taxes & fees
Sep 13 - Sep 14
12. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Debra
₩155,233
₩173,395 total
includes taxes & fees
Oct 12 - Oct 13
13. Williamstown Motel
Williamstown MotelWilliamstown
Ahmet
₩132,660
₩148,182 total
includes taxes & fees
Sep 13 - Sep 14
14. The Villager Motel
The Villager MotelWilliamstown
Rebecca
₩119,260
₩133,209 total
includes taxes & fees
Sep 15 - Sep 16
15. The Springs Motel
The Springs MotelNew Ashford
Elizabeth
₩152,257
₩167,026 total
includes taxes & fees
Sep 13 - Sep 14
16. The Williams Inn
The Williams InnWilliamstown
John
₩260,295
₩290,750 total
includes taxes & fees
Sep 15 - Sep 16
17. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
C. David
₩240,557
₩268,703 total
includes taxes & fees
Sep 22 - Sep 23
18. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Steve
₩170,180
₩190,092 total
includes taxes & fees
Sep 14 - Sep 15
19. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Nancy
₩181,528
₩202,766 total
includes taxes & fees
Sep 28 - Sep 29
20. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
COLLEEN
₩105,860
₩118,246 total
includes taxes & fees
Sep 14 - Sep 15
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
Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting.
See all hotels in Cheshire
Top Cheshire Hotel Reviews
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Great location for Mass Moca"
Vacation Village in the Berkshires
10/10 Excellent
"Beautiful location and views. Spacious room with all amenities."
Berkshire Mountain Lodge
8/10 Good
"Loved having a full Kitchen, lots of space"
Berkshires Untold
10/10 Excellent
"beautiful place, great staff, would love to go back!"
The Yankee Inn
10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
Willows Motel Williamstown
10/10 Excellent
"Awesome staff plus pet-friendly."
Holiday Inn Club Vacations Oak 'n Spruce Resort
8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
Jiminy Peak Mountain Resort
10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
Quality Inn Lee - Lenox South
8/10 Good
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
More cheap stays in Cheshire
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
₩83,214
₩92,950 total
Sep 13 - Sep 14
includes taxes & fees
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
₩141,745
₩158,329 total
Sep 13 - Sep 14
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
₩144,569
₩161,484 total
Sep 24 - Sep 25
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
₩155,440
₩173,627 total
Sep 22 - Sep 23
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
₩170,180
₩190,092 total
Sep 14 - Sep 15
includes taxes & fees
The Whitlock
16 Church St Lenox MA
₩192,491
₩215,013 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very Good! (378 reviews)
