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Berkshires

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Map of Berkshires Hotels

Hotels (69)

B&Bs / Inns (111)

Specialty Lodging (27)

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Hotel on North (Pittsfield) 3.5 of 5
297 North St, Pittsfield, MA 01201-4602
Hotel on North Slideshow
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$170 - $414 Avg. price/night*
Ollie #1 of 69 hotels in Berkshires
Professional photos | Traveler photos (101)
Offers & Announcements Fall for the Berkshires
165 Kemble St, Lenox, MA 01240-2817
Canyon Ranch in Lenox Slideshow
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$1,273 - $2,042 Avg. price/night*
Ollie #2 of 69 hotels in Berkshires
#1 of 13 hotels in Lenox
Traveler photos (182)
445 Pittsfield Rd, Lenox, MA 01240-2132
Hampton Inn & Suites Berkshires-Lenox Slideshow
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$139 - $299 Avg. price/night*
Ollie #3 of 69 hotels in Berkshires
#2 of 13 hotels in Lenox
Professional photos | Traveler photos (431)
Special Offer STOP CLICKING AROUND
1032 South St, Pittsfield, MA 01201-8225
Hilton Garden Inn Lenox Pittsfield Slideshow
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$140 - $310 Avg. price/night*
Ollie #4 of 69 hotels in Berkshires
Professional photos | Traveler photos (37)
Special Offer STOP CLICKING AROUND
Briarcliff Motel (Great Barrington) 2.0 of 5
506 Stockbridge Rd, Great Barrington, MA 01230-1296
Briarcliff Motel Slideshow
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$127 - $206 Avg. price/night*
Ollie #5 of 69 hotels in Berkshires
Professional photos | Traveler photos (82)
231 River St, North Adams, MA 01247-3201
The Porches Inn at MASS MoCA Slideshow
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$204 - $395 Avg. price/night*
Ollie #6 of 69 hotels in Berkshires
  •  The Gem of North Adams. 
  • We really enjoyed porches. It was quality stay with great little touches... more
  • September 26, 2016
Professional photos | Traveler photos (207)
Special Offer Fall for the Berkshires
615 Laurel St, Lee, MA 01238-9180
LakeHouse Inn Slideshow
$195 - $294 Avg. price/night*
Ollie #7 of 69 hotels in Berkshires
#1 of 9 hotels in Lee
Traveler photos (46)
Special Price 10% off room rate
249 Stockbridge Rd, Bldg 1, Great Barrington, MA 01230-1297
Fairfield Inn & Suites Lenox Great Barrington/Berkshires Slideshow
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$163 - $354 Avg. price/night*
Ollie #8 of 69 hotels in Berkshires
  •  A pleasant surprise 
  • Stayed at this hotel and pleasantly surprise at the accommodations of the... more
  • September 29, 2016
Professional photos | Traveler photos (45)
Special Offer Member Rates
435 Laurel St, Lee, MA 01238-9510
Black Swan Inn Berkshires, an Ascend Collection Hotel Slideshow
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$89 - $289 Avg. price/night*
Ollie #9 of 69 hotels in Berkshires
#2 of 9 hotels in Lee
  •  Overnight  
  • We truly enjoyed our stay here, and would come again if we were ever in... more
  • September 29, 2016
Professional photos | Traveler photos (141)
Special Offer Choice Privileges Points
Williamstown Motel (Williamstown) 2.0 of 5
295 Main Street, Williamstown, MA 01267-2610
Williamstown Motel Slideshow
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$71 - $150 Avg. price/night*
Ollie #10 of 69 hotels in Berkshires
Professional photos | Traveler photos (79)
Offers & Announcements Clark Museum Package
The Red Lion Inn (Stockbridge) 3.0 of 5
30 Main St, Box 954, Stockbridge, MA 01262-9701
The Red Lion Inn Slideshow
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$147 - $355 Avg. price/night*
Ollie #11 of 69 hotels in Berkshires
  •  Hotel 
  • I liked this hotel because it has an antique Otis elevator. The room that... more
  • September 26, 2016
Professional photos | Traveler photos (766)
Offers & Announcements Fall for the Berkshires
1350 W Housatonic St, Pittsfield, MA 01201-7514
BEST WESTERN PLUS Berkshire Hills Inn & Suites Slideshow
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$97 - $245 Avg. price/night*
Ollie #12 of 69 hotels in Berkshires
Professional photos | Traveler photos (59)
Special Offer SAVE UP TO 15%
1 Corey Rd, Hancock, MA 01237-9541
Wyndham at Bentley Brook Slideshow
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$118 - $215 Avg. price/night*
Ollie #13 of 69 hotels in Berkshires
Professional photos | Traveler photos (243)
Special Price 15% Off
Yankee Inn (Lenox) 2.5 of 5
461 Pittsfield Rd, Lenox, MA 01240-2132
Yankee Inn Slideshow
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$90 - $200 Avg. price/night*
Ollie #14 of 69 hotels in Berkshires
#3 of 13 hotels in Lenox
  •  Old and Tired 
  • This motel has seen its day. You can see that a renovation has been done... more
  • September 28, 2016
Professional photos | Traveler photos (121)
199 Main St, Lee, MA 01238-1660
Chambery Inn Slideshow
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$144 - $394 Avg. price/night*
Ollie #15 of 69 hotels in Berkshires
#3 of 9 hotels in Lee
Professional photos | Traveler photos (134)
Willows Motel (Williamstown) 2.0 of 5
480 Main St, Route 2, Williamstown, MA 01267-2609
No photo provided
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$82 - $166 Avg. price/night*
Ollie #16 of 69 hotels in Berkshires
  •  Happy repeat guest! 
  • The Willows is a great family run motel. The owners are present on the... more
  • September 27, 2016
Professional photos | Traveler photos (62)
276 Brodie Mountain Rd, Hancock, MA 01237
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$114 - $191 Avg. price/night*
Ollie #17 of 69 hotels in Berkshires
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MAPLE TERRACE MOTEL (Williamstown)
555 Main St, Williamstown, MA 01267-2612
MAPLE TERRACE MOTEL Slideshow
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$87 - $132 Avg. price/night*
Ollie #18 of 69 hotels in Berkshires
  •  Wonderful Motel 
  • This August my wife and I spent a pleasant week in Williamstown staying at... more
  • September 5, 2016
Professional photos | Traveler photos (49)
Blantyre (Lenox) 4.0 of 5
16 Blantyre Rd, Lenox, MA 01240-2776
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$418 - $993 Avg. price/night*
Ollie #19 of 69 hotels in Berkshires
#4 of 13 hotels in Lenox
  •  quick get away 
  • overall excellent with lovely amenities and the service was superior next... more
  • September 28, 2016
Traveler photos (188)
55 Lee Rd, Lenox, MA 01240-2703
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$259 - $504 Avg. price/night*
Ollie #20 of 69 hotels in Berkshires
#5 of 13 hotels in Lenox
  •  Birthday Weekend Away 
  • My wife and I traveled to Cranwell this past weekend for a birthday... more
  • September 26, 2016
Professional photos | Traveler photos (166)