Find hotels in Cheshire, MA from Rp1.231.588
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Check prices for these dates
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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
Rp4.504.444
Rp4.761.181 total
includes taxes & fees
25 Aug - 26 Aug
2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Brooks
Rp1.716.403
Rp2.111.994 total
includes taxes & fees
7 Sept - 8 Sept
3. The Yankee Inn
The Yankee InnLenox
Larry
Rp2.929.575
Rp3.272.335 total
includes taxes & fees
7 Sept - 8 Sept
4. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Richard
Rp1.838.530
Rp2.053.543 total
includes taxes & fees
12 Aug - 13 Aug
5. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Andrea
Rp1.679.555
Rp2.272.709 total
includes taxes & fees
31 Aug - 1 Sept
6. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Christine
Rp2.237.125
Rp2.498.958 total
includes taxes & fees
8 Sept - 9 Sept
7. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
William
Rp2.470.076
Rp2.759.075 total
includes taxes & fees
10 Sept - 11 Sept
8. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Jeremy
Rp1.578.515
Rp1.855.382 total
includes taxes & fees
8 Sept - 9 Sept
9. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
David
Rp2.254.885
Rp2.518.724 total
includes taxes & fees
25 Aug - 26 Aug
10. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
Rp2.023.715
Rp2.260.490 total
includes taxes & fees
30 Aug - 31 Aug
11. The Springs Motel
The Springs MotelNew Ashford
Shakeila
Rp2.885.188
Rp3.165.051 total
includes taxes & fees
9 Sept - 10 Sept
12. Berkshire Inn
Berkshire InnPittsfield
christopher
Rp1.597.772
Rp1.784.711 total
includes taxes & fees
12 Aug - 13 Aug
13. Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
Donna
Rp1.775.322
Rp1.983.036 total
includes taxes & fees
12 Aug - 13 Aug
14. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
hui
Rp3.728.550
Rp4.164.790 total
includes taxes & fees
7 Sept - 8 Sept
15. The Williams Inn
The Williams InnWilliamstown
Thomas
Rp4.244.274
Rp4.740.853 total
includes taxes & fees
16 Aug - 17 Aug
16. Hotel On North
Hotel On NorthPittsfield
Dragana
Rp3.178.145
Rp3.549.988 total
includes taxes & fees
7 Sept - 8 Sept
17. Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
Sandy
Rp2.823.045
Rp3.153.342 total
includes taxes & fees
31 Aug - 1 Sept
18. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
DAVID
Rp1.102.585
Rp1.231.588 total
includes taxes & fees
25 Aug - 26 Aug
19. Berkshire Valley Inn
Berkshire Valley InnWilliamstown
DM
Rp2.812.392
Rp3.141.442 total
includes taxes & fees
12 Aug - 13 Aug
20. Blue Vista Motor Lodge
Blue Vista Motor LodgeNorth Adams
Frederic
Rp4.373.576
Rp4.622.870 total
includes taxes & fees
12 Aug - 13 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
Quality Inn Lee - Lenox South
10/10 Excellent
"Love that it is so close to the turnpike. But never notice any noise. Also real close to a Dunkin, and Shell gas. Very convenient!"
Vacation Village in the Berkshires
8/10 Good
"Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded."
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."
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!"
More cheap stays in Cheshire
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
Rp1.102.585
Rp1.231.588 total
25 Aug - 26 Aug
includes taxes & fees
5.4/10 (867 reviews)
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
Rp1.402.645
Rp1.566.755 total
31 Aug - 1 Sept
includes taxes & fees
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
Rp1.901.561
Rp2.124.044 total
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very good! (1,012 reviews)
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Rp2.023.715
Rp2.260.490 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
Rp2.272.919
Rp2.538.850 total
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (156 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
Rp2.929.575
Rp3.272.335 total
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
