Cheshire Hotels from S$85
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25 Aug - 26 AugTomorrow
26 Aug - 27 AugThis weekend
28 Aug - 30 AugNext weekend
4 Sept - 6 SeptOur top choices for Cheshire hotels
1. Harbour House Inn
Harbour House InnCheshire
Gregory
S$313
includes taxes & fees
7 Sept - 8 Sept
2. The Springs Motel
The Springs MotelNew Ashford
Shakeila
S$166
includes taxes & fees
9 Sept - 10 Sept
3. The Revival House
The Revival HouseAdams
James
S$235
includes taxes & fees
31 Aug - 1 Sept
4. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
S$162
includes taxes & fees
1 Sept - 2 Sept
5. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Nyra
S$137
includes taxes & fees
31 Aug - 1 Sept
6. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
ERICIA
S$85
includes taxes & fees
27 Aug - 28 Aug
7. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
Victoria
S$211
includes taxes & fees
1 Sept - 2 Sept
8. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Myrna
S$169
includes taxes & fees
22 Sept - 23 Sept
9. Berkshire Inn
Berkshire InnPittsfield
Adriana
S$128
includes taxes & fees
27 Aug - 28 Aug
11. The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art HotelAdams
Jenna
S$287
includes taxes & fees
14 Sept - 15 Sept
12. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Jeremy
S$132
includes taxes & fees
9 Sept - 10 Sept
13. The Yankee Inn
The Yankee InnLenox
Karen
S$224
includes taxes & fees
21 Sept - 22 Sept
14. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Richard
S$147
includes taxes & fees
26 Aug - 27 Aug
15. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Annette
S$177
includes taxes & fees
9 Sept - 10 Sept
16. Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
Donna
S$156
includes taxes & fees
26 Aug - 27 Aug
17. Berkshire Valley Inn
Berkshire Valley InnWilliamstown
DM
S$236
includes taxes & fees
23 Sept - 24 Sept
18. Williamstown Motel
Williamstown MotelWilliamstown
Matthew
S$144
includes taxes & fees
7 Sept - 8 Sept
19. The Central Downtown Inn & Suites
The Central Downtown Inn & SuitesPittsfield
Rena
S$140
includes taxes & fees
26 Aug - 27 Aug
20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Ken
S$169
includes taxes & fees
24 Sept - 25 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
Berkshire Mountain Lodge
10/10 Excellent
"Clean room. Nice hotel. Great option in the Lenox area."
Best Western Plus Berkshire Hills Inn & Suites
10/10 Excellent
"Fine place to stay in the Lenox area."
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"BIen situé avec pleins de restaurants accessibe à pied autour. Grand parking sécuritaire en face il y a la caserne de pompiers. Idéalement ce serait bien d'installer des bornes électriques de recharge pour les véhicules électriques. Déjeuner modeste. Pas de protéines. Pâtisseries et fruits bons. Très propre. Personnel courtois"
Quality Inn Lee - Lenox South
8/10 Good
"Clean room, surprisingly comfortable bed. Convenient, functional, for a short stay."
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s pillow, a wonderful indoor and outdoor dance performance venue. We stay there often, and always makes four a cultural experience and wonderful family time."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"I liked the balcony overlooking the lake"
The Yankee Inn
8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
FairBridge Inn Express
10/10 Excellent
"It was very nice and everyone was extremely helpful"
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
More cheap stays in Cheshire
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
S$85
27 Aug - 28 Aug
includes taxes & fees
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
S$112
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (903 reviews)
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
S$155
14 Sept - 15 Sept
includes taxes & fees
8.4/10 Very good! (1,009 reviews)
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
S$162
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very good! (1,012 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
S$169
24 Sept - 25 Sept
includes taxes & fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
S$224
21 Sept - 22 Sept
includes taxes & fees
9.2/10 Wonderful! (1,020 reviews)
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