Find hotels in Cheshire, MA from Rp1.236.582
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Check prices for these dates
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17 Aug - 18 AugTomorrow
18 Aug - 19 AugThis weekend
21 Aug - 23 AugNext weekend
28 Aug - 30 AugOur top choices for Cheshire hotels
1. Harbour House Inn
Harbour House InnCheshire
Gregory
Rp4.522.710
Rp4.780.488 total
includes taxes & fees
31 Aug - 1 Sept
2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
peter
Rp1.548.586
Rp1.925.332 total
includes taxes & fees
31 Aug - 1 Sept
3. The Yankee Inn
The Yankee InnLenox
Karen
Rp2.816.666
Rp3.146.215 total
includes taxes & fees
14 Sept - 15 Sept
4. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Richard
Rp1.845.986
Rp2.061.871 total
includes taxes & fees
18 Aug - 19 Aug
5. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
Rp1.686.366
Rp2.281.926 total
includes taxes & fees
31 Aug - 1 Sept
6. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Annette
Rp2.228.375
Rp2.489.184 total
includes taxes & fees
8 Sept - 9 Sept
7. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
Rp2.031.921
Rp2.269.657 total
includes taxes & fees
30 Aug - 31 Aug
8. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
Victoria
Rp2.500.772
Rp2.793.362 total
includes taxes & fees
7 Sept - 8 Sept
9. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Myrna
Rp2.264.029
Rp2.528.919 total
includes taxes & fees
23 Aug - 24 Aug
10. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Jeremy
Rp1.572.341
Rp1.848.125 total
includes taxes & fees
9 Sept - 10 Sept
11. Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
Donna
Rp1.782.522
Rp1.991.098 total
includes taxes & fees
18 Aug - 19 Aug
12. The Williams Inn
The Williams InnWilliamstown
Thomas
Rp4.530.732
Rp5.060.827 total
includes taxes & fees
19 Aug - 20 Aug
13. Berkshire Inn
Berkshire InnPittsfield
Danielle
Rp1.604.252
Rp1.791.950 total
includes taxes & fees
19 Aug - 20 Aug
14. Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
Sandy
Rp2.551.044
Rp2.849.517 total
includes taxes & fees
30 Aug - 31 Aug
15. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
C. David
Rp3.601.054
Rp4.022.378 total
includes taxes & fees
7 Sept - 8 Sept
16. Blue Vista Motor Lodge
Blue Vista Motor LodgeNorth Adams
Frederic
Rp4.391.311
Rp4.641.616 total
includes taxes & fees
18 Aug - 19 Aug
17. Hotel On North
Hotel On NorthPittsfield
Drew
Rp3.191.033
Rp3.564.384 total
includes taxes & fees
7 Sept - 8 Sept
18. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
DAVID
Rp1.107.057
Rp1.236.582 total
includes taxes & fees
19 Aug - 20 Aug
19. The Springs Motel
The Springs MotelNew Ashford
Shakeila
Rp2.226.146
Rp2.442.082 total
includes taxes & fees
13 Sept - 14 Sept
20. Berkshire Valley Inn
Berkshire Valley InnWilliamstown
DM
Rp2.968.195
Rp3.315.474 total
includes taxes & fees
18 Aug - 19 Aug
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
Vacation Village in the Berkshires
10/10 Excellent
"Place was clean and well equipped, pool and amenities were great too !"
Berkshires Untold
10/10 Excellent
"Pleasant stay and Sarah made a bouquet of flowers for my daughter’s birthday..a fellow Leo!"
Berkshire Mountain Lodge
10/10 Excellent
"Very nice stay. Room can be a bit noisy. Overall great experience."
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
8/10 Good
"The location just off busy route 20 was a minus, especially since it is difficult to make a left hand turn out of the property with the heavy traffic. The hotel itself was clean, modern and comfortable. All staff were friendly and helpful. The breakfast was generous and well prepared/presented. We enjoyed the pool, hot tub and the exercise room."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
8/10 Good
"Very nice, clean, good breakfast. Only complaint was that it was very expensive because we booked last minute and it the peak season. I would stay again but not at the price we were charged."
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"The location was excellent, and the roads between Lee and Stockbridge, and in a lovely, secluded area. The rooms were spacious, ours included a living room, dining and kitchen area, and upstairs bedroom with spacious closet and bathroom. The price was reasonable. It was very quiet and well maintained. There was a lot for kids to do -- swimming pool and movies. We would go there again."
The Whitlock
10/10 Excellent
"Beautiful room comfortable bed"
The Cornell Inn, Lenox & The Berkshires
8/10 Good
"Bed not very comfortable.."
More cheap stays in Cheshire
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
Rp1.107.057
Rp1.236.582 total
19 Aug - 20 Aug
includes taxes & fees
5.4/10 (874 reviews)
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
Rp1.408.333
Rp1.573.108 total
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (894 reviews)
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
Rp1.909.272
Rp2.132.656 total
31 Aug - 1 Sept
includes taxes & fees
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Rp2.031.921
Rp2.269.657 total
30 Aug - 31 Aug
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Rp2.121.413
Rp2.369.618 total
14 Sept - 15 Sept
includes taxes & fees
9.4/10 Exceptional! (164 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
Rp2.816.666
Rp3.146.215 total
14 Sept - 15 Sept
includes taxes & fees
