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Berkshires

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Map of Berkshires Hotels

Hotels (69)

B&Bs / Inns (112)

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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$164 - $440 Avg. price/night*
Ollie #1 of 69 hotels in Berkshires
Professional photos | Traveler photos (94)
1032 South St, Pittsfield, MA 01201-8225
Hilton Garden Inn Lenox Pittsfield Slideshow
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$131 - $421 Avg. price/night*
Ollie #2 of 69 hotels in Berkshires
Professional photos | Traveler photos (31)
Special Offer STOP CLICKING AROUND
445 Pittsfield Rd, Lenox, MA 01240-2132
Hampton Inn & Suites Berkshires-Lenox Slideshow
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$154 - $387 Avg. price/night*
Ollie #3 of 69 hotels in Berkshires
#1 of 13 hotels in Lenox
Professional photos | Traveler photos (431)
Special Offer STOP CLICKING AROUND
231 River St, North Adams, MA 01247-3201
The Porches Inn at MASS MoCA Slideshow
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$185 - $417 Avg. price/night*
Ollie #4 of 69 hotels in Berkshires
  •  Positively Charming 
  • The look and feel of this inn is definitely modern spin on the classic... more
  • August 29, 2016
Professional photos | Traveler photos (184)
165 Kemble St, Lenox, MA 01240-2817
Canyon Ranch in Lenox Slideshow
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$1,258 - $2,056 Avg. price/night*
Ollie #5 of 69 hotels in Berkshires
#2 of 13 hotels in Lenox
  •  Wonderful Visit! 
  • I just got back from a weekend at the Canyon Ranch and it was absolutely... more
  • August 8, 2016
Traveler photos (175)
Briarcliff Motel (Great Barrington) 2.0 of 5
506 Stockbridge Rd, Great Barrington, MA 01230-1296
Briarcliff Motel Slideshow
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$155 - $242 Avg. price/night*
Ollie #6 of 69 hotels in Berkshires
Professional photos | Traveler photos (82)
249 Stockbridge Rd, Bldg 1, Great Barrington, MA 01230-1297
Fairfield Inn & Suites Lenox Great Barrington/Berkshires Slideshow
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$157 - $374 Avg. price/night*
Ollie #7 of 69 hotels in Berkshires
Professional photos | Traveler photos (45)
Special Offer Member Rates
Williamstown Motel (Williamstown) 2.0 of 5
295 Main St, Williamstown, MA 01267-2610
Williamstown Motel Slideshow
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$80 - $155 Avg. price/night*
Ollie #8 of 69 hotels in Berkshires
Professional photos | Traveler photos (79)
Offers & Announcements Clark Museum Package
435 Laurel St, Lee, MA 01238-9510
Black Swan Inn Berkshires, an Ascend Collection Hotel Slideshow
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$95 - $359 Avg. price/night*
Ollie #9 of 69 hotels in Berkshires
#1 of 9 hotels in Lee
  •  Totally Dog Friendly 
  • This hotel is quite near Tanglewood to our delight. My wife booked the... more
  • August 28, 2016
Professional photos | Traveler photos (121)
Special Offer Choice Privileges Points
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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$146 - $391 Avg. price/night*
Ollie #10 of 69 hotels in Berkshires
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1350 W Housatonic St, Pittsfield, MA 01201-7514
BEST WESTERN PLUS Berkshire Hills Inn & Suites Slideshow
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$101 - $287 Avg. price/night*
Ollie #11 of 69 hotels in Berkshires
  •  A go to Hotel 
  • Stayed here a few times when visiting BSO in Lenox, MA. Always happy with... more
  • August 23, 2016
Professional photos | Traveler photos (59)
615 Laurel St, Lee, MA 01238-9180
LakeHouse Inn Slideshow
$223 - $321 Avg. price/night*
Ollie #12 of 69 hotels in Berkshires
#2 of 9 hotels in Lee
Traveler photos (43)
1 Corey Rd, Hancock, MA 01237-9541
Wyndham at Bentley Brook Slideshow
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$118 - $273 Avg. price/night*
Ollie #13 of 69 hotels in Berkshires
Professional photos | Traveler photos (243)
Special Price 15% Off
199 Main St, Lee, MA 01238-1660
Chambery Inn Slideshow
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$145 - $327 Avg. price/night*
Ollie #14 of 69 hotels in Berkshires
#3 of 9 hotels in Lee
  •  Very pleasant surprise 
  • Made a last minute reservation when I was going to see my daughter dance... more
  • August 29, 2016
Professional photos | Traveler photos (130)
Yankee Inn (Lenox) 2.0 of 5
461 Pittsfield Rd, Lenox, MA 01240-2132
Yankee Inn Slideshow
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$92 - $251 Avg. price/night*
Ollie #15 of 69 hotels in Berkshires
#3 of 13 hotels in Lenox
Professional photos | Traveler photos (121)
MAPLE TERRACE MOTEL (Williamstown)
555 Main St, Williamstown, MA 01267-2612
MAPLE TERRACE MOTEL Slideshow
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$120 - $154 Avg. price/night*
Ollie #16 of 69 hotels in Berkshires
  •  A small gem 
  • Basic everything, nothing extra but everything you would want. And a pool... more
  • August 22, 2016
Professional photos | Traveler photos (49)
276 Brodie Mountain Rd, Hancock, MA 01237
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$114 - $190 Avg. price/night*
Ollie #17 of 69 hotels in Berkshires
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Blantyre (Lenox) 4.0 of 5
16 Blantyre Rd, Lenox, MA 01240-2776
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$526 - $888 Avg. price/night*
Ollie #18 of 69 hotels in Berkshires
#4 of 13 hotels in Lenox
Traveler photos (179)
Willows Motel (Williamstown) 2.0 of 5
480 Main St, Route 2, Williamstown, MA 01267-2609
Willows Motel Slideshow
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$82 - $176 Avg. price/night*
Ollie #19 of 69 hotels in Berkshires
Professional photos | Traveler photos (64)
Monument Mountain Motel (Great Barrington) 2.5 of 5
247 Stockbridge Rd, Route 7, Great Barrington, MA 01230-1297
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$76 - $227 Avg. price/night*
Ollie #20 of 69 hotels in Berkshires
Professional photos | Traveler photos (39)
Special Offer call for best rates