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Berkshires

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Map of Berkshires Hotels

Hotels (71)

B&Bs / Inns (94)

Specialty Lodging (30)

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615 Laurel St, Lee, MA 01238-9180
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$162 - $260 Avg. price/night*
Ollie #1 of 71 hotels in Berkshires
#1 of 9 hotels in Lee
  •  The perfect getaway 
  • My friend and I stayed at the LakeHouse Inn for our girl's weekend getaway... more
  • November 5, 2018
Traveler photos (143)
91 Walker St, Lenox, MA 01240-2719
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$197 - $289 Avg. price/night*
Ollie #2 of 71 hotels in Berkshires
#1 of 16 hotels in Lenox
Traveler photos (310)
Offers & Announcements Classic Romance Package...
Hotel on North (Pittsfield) 3.5 of 5
297 North St, Pittsfield, MA 01201-4602
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$164 - $289 Avg. price/night*
Ollie #3 of 71 hotels in Berkshires
Traveler photos (258)
Offers & Announcements SKI & STAY PACKAGE
135 Main St, Lenox, MA 01240-2396
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$178 - $352 Avg. price/night*
Ollie #4 of 71 hotels in Berkshires
#2 of 16 hotels in Lenox
  •  WOW!!! 
  • Our weekend at the inn was perfect. You feel welcomed and at home from the... more
  • December 10, 2018
Traveler photos (373)
Special Price Save up to 33%
MAPLE TERRACE MOTEL (Williamstown) 2.5 of 5
555 Main St, Williamstown, MA 01267-2612
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$68 - $120 Avg. price/night*
Ollie #5 of 71 hotels in Berkshires
Traveler photos (201)
Offers & Announcements Ski & Stay Packages!!
1032 South St, Pittsfield, MA 01201-8225
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$120 - $235 Avg. price/night*
Ollie #6 of 71 hotels in Berkshires
  •  Great hotel and staff 
  • I really enjoyed my stay here. The room was beautiful and the hotel was in... more
  • December 2, 2018
Traveler photos (78)
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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$97 - $189 Avg. price/night*
Ollie #7 of 71 hotels in Berkshires
Traveler photos (109)
Offers & Announcements 15% off room rate
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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$566 - $662 Avg. price/night*
Ollie #8 of 71 hotels in Berkshires
#3 of 16 hotels in Lenox
  •  Disappointing 
  • We have a tradition of gong to Blantyre for Dinner around the holidays. We... more
  • December 11, 2018
Traveler photos (313)
445 Pittsfield Rd, Lenox, MA 01240-2132
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$121 - $231 Avg. price/night*
Ollie #9 of 71 hotels in Berkshires
#4 of 16 hotels in Lenox
  •  Great one night stay 
  • Good choice for our night away. Friendly staff, clean and large room... more
  • December 11, 2018
Traveler photos (464)
Special Offer Double Points, Every...
249 Stockbridge Rd, Route 7, Great Barrington, MA 01230-1297
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$139 - $309 Avg. price/night*
Ollie #10 of 71 hotels in Berkshires
Traveler photos (49)
Special Offer Unlock Member Rates!
165 Kemble St, Lenox, MA 01240-2817
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$653 - $1,189 Avg. price/night*
Ollie #11 of 71 hotels in Berkshires
#5 of 16 hotels in Lenox
  •  Canyon Ranch 
  • Phenomenal! May be the best overall vacation for many reasons. Staff... more
  • December 8, 2018
Traveler photos (209)
Special Offer Save Now
199 Main St, Lee, MA 01238-1660
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$98 - $303 Avg. price/night*
Ollie #12 of 71 hotels in Berkshires
#2 of 9 hotels in Lee
Traveler photos (216)
Offers & Announcements UP TO 50% OFF BOOK...
40 Plunkett St, Lenox, MA 01240-2704
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$96 - $187 Avg. price/night*
Ollie #13 of 71 hotels in Berkshires
#6 of 16 hotels in Lenox
Traveler photos (158)
231 River St, North Adams, MA 01247-3201
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$175 - $321 Avg. price/night*
Ollie #14 of 71 hotels in Berkshires
  •  Our get away Inn 
  • The Porches is a great get away from the normal routine. The Inn is... more
  • December 7, 2018
Traveler photos (261)
Offers & Announcements MASS MoCA Package
256 Stockbridge Rd, Route 7, Great Barrington, MA 01230-1269
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$66 - $128 Avg. price/night*
Ollie #15 of 71 hotels in Berkshires
  •  Good for the buck 
  • Clean, and very convenient to all attractions in the upper Massachusetts... more
  • November 12, 2018
Traveler photos (55)
Special Offer CALL FOR BEST RATES!
Monument Mountain Motel (Great Barrington) 2.5 of 5
247 Stockbridge Rd, Route 7, Great Barrington, MA 01230-1297
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$65 - $334 Avg. price/night*
Ollie #16 of 71 hotels in Berkshires
  •  A Quick Getaway  
  • Drove up to Great Barrington for an overnight. Great place. Very clean... more
  • December 8, 2018
Traveler photos (43)
Williamstown Motel (Williamstown) 2.0 of 5
295 Main St, Williamstown, MA 01267-2610
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$63 - $106 Avg. price/night*
Ollie #17 of 71 hotels in Berkshires
  •  Great location 
  • The room was very clean and cozy. Had no complaints at all. Thank you so... more
  • December 10, 2018
Traveler photos (111)
1 Corey Rd, Hancock, MA 01237-9541
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$113 - $362 Avg. price/night*
Ollie #18 of 71 hotels in Berkshires
Traveler photos (352)
Special Offer 15% Off
Yankee Inn (Lenox) 2.5 of 5
461 Pittsfield Rd, Lenox, MA 01240-2132
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$86 - $137 Avg. price/night*
Ollie #19 of 71 hotels in Berkshires
#7 of 16 hotels in Lenox
  •  Yankee Inn Is Superb! 
  • I have had the pleasure of staying at the Yankee in several times during... more
  • December 11, 2018
Traveler photos (156)
1350 W Housatonic St, Pittsfield, MA 01201-7514
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$86 - $148 Avg. price/night*
Ollie #20 of 71 hotels in Berkshires
  •  Fireplace suites 
  • We were out for my daughters baby shower. I travelled from Boston with my... more
  • November 2, 2018
Traveler photos (89)
Offers & Announcements BOOK DIRECT & SAVE