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Map of Berkshires Hotels

Hotels (71)

B&Bs / Inns (107)

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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$163 - $253 Avg. price/night*
Ollie #1 of 71 hotels in Berkshires
Professional photos | Traveler photos (142)
Special Offer Date Night Package
91 Walker St, Lenox, MA 01240-2719
Hampton Terrace Inn Slideshow
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$275 - $328 Avg. price/night*
Ollie #2 of 71 hotels in Berkshires
#1 of 14 hotels in Lenox
Professional photos | Traveler photos (282)
Offers & Announcements 3rd Night 50% off
615 Laurel St, Lee, MA 01238-9180
LakeHouse Inn Slideshow
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$215 - $334 Avg. price/night*
Ollie #3 of 71 hotels in Berkshires
#1 of 9 hotels in Lee
Traveler photos (51)
165 Kemble St, Lenox, MA 01240-2817
Canyon Ranch in Lenox Slideshow
$653 - $1,189 Avg. price/night*
Ollie #4 of 71 hotels in Berkshires
#2 of 14 hotels in Lenox
  •  Fabulous 
  • I spent 3 nights here in early November and enjoyed every moment. The... more
  • December 5, 2016
Traveler photos (185)
445 Pittsfield Rd, Lenox, MA 01240
Hampton Inn & Suites Berkshires-Lenox Slideshow
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$121 - $222 Avg. price/night*
Ollie #5 of 71 hotels in Berkshires
#3 of 14 hotels in Lenox
Professional photos | Traveler photos (441)
Special Offer December Flash Sale
1032 South St, Pittsfield, MA 01201-8225
Hilton Garden Inn Lenox Pittsfield Slideshow
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$122 - $242 Avg. price/night*
Ollie #6 of 71 hotels in Berkshires
  •  Great place to stay!! 
  • The Hilton Garden Inn was a great place to stay! The staff was very... more
  • December 5, 2016
Professional photos | Traveler photos (37)
Special Offer December Flash Sale
Briarcliff Motel (Great Barrington) 2.0 of 5
506 Stockbridge Rd, Great Barrington, MA 01230-1296
Briarcliff Motel Slideshow
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$99 - $173 Avg. price/night*
Ollie #7 of 71 hotels in Berkshires
  •  September 
  • As members of the Ford-V8 Antique Club we went to the Berkshires to find a... more
  • November 9, 2016
Professional photos | Traveler photos (83)
231 River St, North Adams, MA 01247-3201
The Porches Inn at MASS MoCA Slideshow
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$164 - $299 Avg. price/night*
Ollie #8 of 71 hotels in Berkshires
Professional photos | Traveler photos (225)
Offers & Announcements Porches Ski & Stay
Williamstown Motel (Williamstown) 2.0 of 5
295 Main Street, Williamstown, MA 01267-2610
Williamstown Motel Slideshow
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$67 - $88 Avg. price/night*
Ollie #9 of 71 hotels in Berkshires
Professional photos | Traveler photos (97)
Offers & Announcements BOOK DIRECT AND SAVE $$
435 Laurel St, Lee, MA 01238-9510
Black Swan Inn Berkshires, an Ascend Collection Hotel Slideshow
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$83 - $154 Avg. price/night*
Ollie #10 of 71 hotels in Berkshires
#2 of 9 hotels in Lee
Professional photos | Traveler photos (185)
Special Offer Choice Privileges Points
249 Stockbridge Rd, Bldg 1, Great Barrington, MA 01230-1297
Fairfield Inn & Suites Lenox Great Barrington/Berkshires Slideshow
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$138 - $297 Avg. price/night*
Ollie #11 of 71 hotels in Berkshires
Professional photos | Traveler photos (45)
Special Offer Member Rates
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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$150 - $310 Avg. price/night*
Ollie #12 of 71 hotels in Berkshires
Professional photos | Traveler photos (792)
Special Offer Date Night Package
1 Corey Rd, Hancock, MA 01237-9541
Wyndham at Bentley Brook Slideshow
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$135 - $345 Avg. price/night*
Ollie #13 of 71 hotels in Berkshires
Professional photos | Traveler photos (252)
Special Offer 15% Off
1350 W Housatonic St, Pittsfield, MA 01201-7514
BEST WESTERN PLUS Berkshire Hills Inn & Suites Slideshow
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$88 - $146 Avg. price/night*
Ollie #14 of 71 hotels in Berkshires
Professional photos | Traveler photos (59)
Special Offer BOOK DIRECT AND SAVE
Willows Motel (Williamstown) 2.0 of 5
480 Main St, Route 2, Williamstown, MA 01267-2609
Willows Motel Slideshow
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$83 - $112 Avg. price/night*
Ollie #15 of 71 hotels in Berkshires
Professional photos | Traveler photos (69)
Blantyre (Lenox) 4.0 of 5
16 Blantyre Rd, Lenox, MA 01240-2776
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$417 - $897 Avg. price/night*
Ollie #16 of 71 hotels in Berkshires
#4 of 14 hotels in Lenox
  •  Relaxing and pampering 
  • There are not many places left to visit where as soon as you drive onto... more
  • December 4, 2016
Traveler photos (214)
276 Brodie Mountain Rd, Hancock, MA 01237
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$111 - $169 Avg. price/night*
Ollie #17 of 71 hotels in Berkshires
Professional photos | Traveler photos (267)
Yankee Inn (Lenox) 2.5 of 5
461 Pittsfield Rd, Lenox, MA 01240-2132
Yankee Inn Slideshow
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$80 - $138 Avg. price/night*
Ollie #18 of 71 hotels in Berkshires
#5 of 14 hotels in Lenox
  •  Pleasing 
  • Wow this was such a nice motel to stay at for a night. The service was... more
  • December 5, 2016
Professional photos | Traveler photos (121)
199 Main St, Lee, MA 01238-1660
Chambery Inn Slideshow
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$126 - $261 Avg. price/night*
Ollie #19 of 71 hotels in Berkshires
#3 of 9 hotels in Lee
  •  A cozy place to stay 
  • A charming inn with pleasant appointments. A repurposed schoolhouse, the... more
  • November 22, 2016
Professional photos | Traveler photos (138)
Special Offer 10% Off Spa Services
MAPLE TERRACE MOTEL (Williamstown) 2.5 of 5
555 Main St, Williamstown, MA 01267-2612
MAPLE TERRACE MOTEL Slideshow
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$65 - $99 Avg. price/night*
Ollie #20 of 71 hotels in Berkshires
  •  All four seasons 
  • I have stayed here many times in every season, beginning in 2001... more
  • November 18, 2016
Professional photos | Traveler photos (57)
Special Offer Stay & Ski