
Find hotels in Cheshire, MA from ₩95,470
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Go beyond your typical stay in Cheshire
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Check prices for these dates
Tonight
Aug 30 - Aug 31Tomorrow
Aug 31 - Sep 1Next weekend
Sep 4 - Sep 6In two weeks
Sep 11 - Sep 13Our top choices for Cheshire hotels




1. Harbour House Inn
Harbour House InnCheshire
Gregory
₩349,177
₩369,081 total
includes taxes & fees
Aug 31 - Sep 1




2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Alex
₩133,053
₩163,718 total
includes taxes & fees
Sep 1 - Sep 2




3. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Richard
₩116,370
₩129,982 total
includes taxes & fees
Sep 1 - Sep 2




4. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Annette
₩172,043
₩192,179 total
includes taxes & fees
Sep 9 - Sep 10




5. The Yankee Inn
The Yankee InnLenox
Karen
₩209,204
₩233,675 total
includes taxes & fees
Sep 27 - Sep 28




6. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
₩130,196
₩176,176 total
includes taxes & fees
Aug 31 - Sep 1




7. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Nicole
₩162,408
₩181,415 total
includes taxes & fees
Sep 7 - Sep 8




8. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Janis
₩121,393
₩142,685 total
includes taxes & fees
Sep 9 - Sep 10




9. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
Peter
₩209,204
₩233,681 total
includes taxes & fees
Sep 20 - Sep 21




10. The Villager Motel
The Villager MotelWilliamstown
Rebecca
₩122,494
₩136,822 total
includes taxes & fees
Sep 1 - Sep 2




11. Hotel On North
Hotel On NorthPittsfield
Drew
₩246,365
₩275,190 total
includes taxes & fees
Sep 7 - Sep 8




12. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
₩157,990
₩176,475 total
includes taxes & fees
Sep 20 - Sep 21




13. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
Sheila
₩108,731
₩121,453 total
includes taxes & fees
Aug 31 - Sep 1




14. The Springs Motel
The Springs MotelNew Ashford
Elizabeth
₩168,773
₩185,144 total
includes taxes & fees
Aug 31 - Sep 1




15. Berkshire Inn
Berkshire InnPittsfield
Adriana
₩118,351
₩132,198 total
includes taxes & fees
Aug 31 - Sep 1




16. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Nancy
₩170,878
₩190,872 total
includes taxes & fees
Sep 13 - Sep 14




17. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Ken
₩162,408
₩181,415 total
includes taxes & fees
Sep 8 - Sep 9




18. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
C. David
₩247,081
₩275,990 total
includes taxes & fees
Sep 27 - Sep 28




19. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
ERICIA
₩85,470
₩95,470 total
includes taxes & fees
Sep 13 - Sep 14




20. Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
Christopher
₩196,954
₩219,997 total
includes taxes & fees
Aug 31 - Sep 1
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
The Yankee Inn
8/10 Good
"Independent option convenient to Tanglewood. Spacious room and facility. Breakfast included but needs better coffee and some other tweaks."
Berkshires Untold
10/10 Excellent
"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."
Vacation Village in the Berkshires
10/10 Excellent
"Friendly and professional staff. Check in quick and easy. Will definitely stay again"
Quality Inn Lee - Lenox South
8/10 Good
"Ok hotel"
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Amazing time. Stayed in the Presidential units. Worth it."
Hotel On North
10/10 Excellent
"One of my favorite hotels in America - for real!"
The Red Lion Inn
10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
The Cornell Inn, Lenox & The Berkshires
10/10 Excellent
"Room was"
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
10/10 Excellent
"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"
More cheap stays in Cheshire

FairBridge Inn Express
16 Cheshire Road Pittsfield MA
₩85,470
₩95,470 total
Sep 13 - Sep 14
includes taxes & fees

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
₩108,731
₩121,453 total
Aug 31 - Sep 1
includes taxes & fees

Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
₩150,916
₩168,573 total
Sep 20 - Sep 21
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)

Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
₩157,990
₩176,475 total
Sep 20 - Sep 21
includes taxes & fees

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
₩162,408
₩181,415 total
Sep 8 - Sep 9
includes taxes & fees
9.4/10 Exceptional! (176 reviews)

The Yankee Inn
461 Pittsfield Rd Lenox MA
₩209,204
₩233,675 total
Sep 27 - Sep 28
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)

