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Berkshires

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Map of Berkshires Hotels

Hotels (70)

B&Bs / Inns (94)

Specialty Lodging (27)

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Hotels Travelers Trust

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615 Laurel St, Lee, MA 01238-9180
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$223 - $672 Avg. price/night*
Ollie #1 of 70 hotels in Berkshires
#1 of 9 hotels in Lee
Traveler photos (129)
91 Walker St, Lenox, MA 01240-2719
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$198 - $404 Avg. price/night*
Ollie #2 of 70 hotels in Berkshires
#1 of 15 hotels in Lenox
  •  "Great Experience" 
  • Just returned from a trip to the Berkshires, and my wife and I are glad we... more
  • June 19, 2018
Professional photos | Traveler photos (307)
Special Offer Peak Midweek Savings
135 Main St, Lenox, MA 01240-2396
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$203 - $447 Avg. price/night*
Ollie #3 of 70 hotels in Berkshires
#2 of 15 hotels in Lenox
  •  Just amazing! 
  • What an amazing place! We had an all girls getaway here and we were... more
  • June 18, 2018
Traveler photos (371)
Hotel on North (Pittsfield) 3.5 of 5
297 North St, Pittsfield, MA 01201-4602
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$160 - $419 Avg. price/night*
Ollie #4 of 70 hotels in Berkshires
Professional photos | Traveler photos (234)
Offers & Announcements Take a Hike Package
Certificate of Excellence
Travelers' Choice® 2018 Winner Small Hotels
 
Blantyre (Lenox) 4.0 of 5
16 Blantyre Rd, Lenox, MA 01240-2776
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$606 - $2,726 Avg. price/night*
Ollie #5 of 70 hotels in Berkshires
#3 of 15 hotels in Lenox
  •  Wonderful gem! 
  • We stayed at the Blantyre while attending a wedding in the area and stayed... more
  • June 18, 2018
Traveler photos (250)
MAPLE TERRACE MOTEL (Williamstown) 2.5 of 5
555 Main St, Williamstown, MA 01267-2612
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$108 - $171 Avg. price/night*
Ollie #6 of 70 hotels in Berkshires
  •  Lovely stay 
  • Very nice motel. Rooms a little dated, but very clean. Able to park in... more
  • June 19, 2018
Professional photos | Traveler photos (172)
Special Offer BOOK DIRECT & SAVE!
1032 South St, Pittsfield, MA 01201-8225
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$139 - $455 Avg. price/night*
Ollie #7 of 70 hotels in Berkshires
Professional photos | Traveler photos (75)
Special Offer Double Points, Every...
Briarcliff Motel (Great Barrington) 2.0 of 5
506 Stockbridge Rd, Great Barrington, MA 01230-1296
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$148 - $265 Avg. price/night*
Ollie #8 of 70 hotels in Berkshires
  •  Great Value 
  • Stopped for an overnight to and from Vermont from NJ. Just a few minutes... more
  • May 19, 2018
Traveler photos (107)
Announcement Escape Brooklyn says:
445 Pittsfield Rd, Lenox, MA 01240-2132
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$127 - $451 Avg. price/night*
Ollie #9 of 70 hotels in Berkshires
#4 of 15 hotels in Lenox
Professional photos | Traveler photos (466)
Special Offer Double Points, Every...
165 Kemble St, Lenox, MA 01240-2817
$653 - $1,189 Avg. price/night*
Ollie #10 of 70 hotels in Berkshires
#5 of 15 hotels in Lenox
Traveler photos (249)
231 River St, North Adams, MA 01247-3201
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$187 - $354 Avg. price/night*
Ollie #11 of 70 hotels in Berkshires
Professional photos | Traveler photos (259)
Offers & Announcements ArtCountry Package
199 Main St, Lee, MA 01238-1660
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$165 - $387 Avg. price/night*
Ollie #12 of 70 hotels in Berkshires
#2 of 9 hotels in Lee
  •  Roomy, quiet room. 
  • We really enjoyed our stay at Chambery Inn. The room size encouraged us... more
  • May 21, 2018
Traveler photos (200)
249 Stockbridge Rd, Route 7, Great Barrington, MA 01230-1297
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$159 - $441 Avg. price/night*
Ollie #13 of 70 hotels in Berkshires
  •  Extremely Pleased 
  • The minute I arrived to check in, we were greeted by the person who... more
  • June 17, 2018
Professional photos | Traveler photos (49)
Special Offer Member Rates
Monument Mountain Motel (Great Barrington) 2.5 of 5
247 Stockbridge Rd, Route 7, Great Barrington, MA 01230-1297
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$76 - $206 Avg. price/night*
Ollie #14 of 70 hotels in Berkshires
  •  Clean, tidy, perfect 
  • Awesome room, super clean, we ate a good breakfast across the street. If... more
  • June 15, 2018
Professional photos | Traveler photos (43)
Special Offer Call Directly for 10...
256 Stockbridge Rd, Route 7, Great Barrington, MA 01230-1269
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$76 - $250 Avg. price/night*
Ollie #15 of 70 hotels in Berkshires
Traveler photos (50)
Special Offer CALL FOR BEST RATES!
Williamstown Motel (Williamstown) 2.0 of 5
295 Main St, Williamstown, MA 01267-2610
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$85 - $204 Avg. price/night*
Ollie #16 of 70 hotels in Berkshires
  •  Memorial day weekend 
  • Had a great time in the Berkshires..all made by the wonderful service and... more
  • May 31, 2018
Traveler photos (110)
Yankee Inn (Lenox) 2.5 of 5
461 Pittsfield Rd, Lenox, MA 01240-2132
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$101 - $316 Avg. price/night*
Ollie #17 of 70 hotels in Berkshires
#6 of 15 hotels in Lenox
Professional photos | Traveler photos (128)
1 Corey Rd, Hancock, MA 01237-9541
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$142 - $252 Avg. price/night*
Ollie #18 of 70 hotels in Berkshires
Professional photos | Traveler photos (313)
1350 W Housatonic St, Pittsfield, MA 01201-7514
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$103 - $299 Avg. price/night*
Ollie #19 of 70 hotels in Berkshires
  •  Great place 
  • Have stayed here numerous times while in the area for personal reasons.The... more
  • June 18, 2018
Professional photos | Traveler photos (64)
Special Offer BOOK DIRECT & SAVE
435 Laurel St, Lee, MA 01238-9510
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$104 - $364 Avg. price/night*
Ollie #20 of 70 hotels in Berkshires
#3 of 9 hotels in Lee
  •  Disappointing 
  • A friend and I stayed at the Black Swan Inn in Lee, Ma. just a few days... more
  • June 18, 2018
Professional photos | Traveler photos (260)