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Map of Berkshires Hotels

Hotels (68)

B&Bs / Inns (93)

Specialty Lodging (27)

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91 Walker St, Lenox, MA 01240-2719
Hampton Terrace Inn Slideshow
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$277 - $337 Avg. price/night*
Ollie #1 of 68 hotels in Berkshires
#1 of 14 hotels in Lenox
Professional photos | Traveler photos (282)
Offers & Announcements Third Night 50% Off!
Hotel on North (Pittsfield) 3.5 of 5
297 North St, Pittsfield, MA 01201-4602
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$154 - $288 Avg. price/night*
Ollie #2 of 68 hotels in Berkshires
Professional photos | Traveler photos (150)
Special Offer Ski & Stay package
445 Pittsfield Rd, Lenox, MA 01240
Hampton Inn & Suites Berkshires-Lenox Slideshow
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$119 - $299 Avg. price/night*
Ollie #3 of 68 hotels in Berkshires
#2 of 14 hotels in Lenox
  •  nice stay 
  • one night stay in Lenox for a Friday night. Best price on web doing the... more
  • January 21, 2017
Professional photos | Traveler photos (435)
Special Offer STOP CLICKING AROUND
615 Laurel St, Lee, MA 01238-9180
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$164 - $334 Avg. price/night*
Ollie #4 of 68 hotels in Berkshires
#1 of 9 hotels in Lee
Professional photos | Traveler photos (86)
1032 South St, Pittsfield, MA 01201-8225
Hilton Garden Inn Lenox Pittsfield Slideshow
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$122 - $253 Avg. price/night*
Ollie #5 of 68 hotels in Berkshires
  •  Modern & Contemporary 
  • Attended a weekend course at Kripalu and wanted a conveniently located... more
  • January 21, 2017
Professional photos | Traveler photos (37)
Special Offer STOP CLICKING AROUND
165 Kemble St, Lenox, MA 01240-2817
$653 - $1,189 Avg. price/night*
Ollie #6 of 68 hotels in Berkshires
#3 of 14 hotels in Lenox
Traveler photos (188)
231 River St, North Adams, MA 01247-3201
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$122 - $311 Avg. price/night*
Ollie #7 of 68 hotels in Berkshires
  •  Charming hotel 
  • This is the third time I've stayed here, it's a delightful hotel... more
  • January 14, 2017
Professional photos | Traveler photos (228)
Special Offer Porches Ski & Stay
Briarcliff Motel (Great Barrington) 2.0 of 5
506 Stockbridge Rd, Great Barrington, MA 01230-1296
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$99 - $173 Avg. price/night*
Ollie #8 of 68 hotels in Berkshires
  •  We're huge fans 
  • We spend every winter weekend at the Briarcliff because of the easy access... more
  • January 11, 2017
Professional photos | Traveler photos (83)
435 Laurel St, Lee, MA 01238-9510
Black Swan Inn Berkshires, an Ascend Collection Hotel Slideshow
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$84 - $188 Avg. price/night*
Ollie #9 of 68 hotels in Berkshires
#2 of 9 hotels in Lee
  •  Best of the Three R's! 
  • Relaxing, romantic, recreational and perfect for a fall getaway. The inn... more
  • January 13, 2017
Professional photos | Traveler photos (173)
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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$67 - $109 Avg. price/night*
Ollie #10 of 68 hotels in Berkshires
  •  Affordable and decent 
  • Great location for a visit to the Clark and Mass MOCA. We also met folks... more
  • January 9, 2017
Professional photos | Traveler photos (97)
Offers & Announcements STAY AND SKI
249 Stockbridge Rd, Bldg 1, Great Barrington, MA 01230-1297
Fairfield Inn & Suites Lenox Great Barrington/Berkshires Slideshow
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$143 - $339 Avg. price/night*
Ollie #11 of 68 hotels in Berkshires
  •  Perfect experience 
  • My sister and I spent a night here for a girls night away from our busy... more
  • January 16, 2017
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
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$155 - $312 Avg. price/night*
Ollie #12 of 68 hotels in Berkshires
  •  Overrated  
  • The dining room is beautiful. The piano is very pleasent but the guests... more
  • January 20, 2017
Professional photos | Traveler photos (796)
Special Offer Ski Break Package
1 Corey Rd, Hancock, MA 01237-9541
Wyndham at Bentley Brook Slideshow
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$141 - $360 Avg. price/night*
Ollie #13 of 68 hotels in Berkshires
Professional photos | Traveler photos (255)
Special Price 15% Off
1350 W Housatonic St, Pittsfield, MA 01201-7514
BEST WESTERN PLUS Berkshire Hills Inn & Suites Slideshow
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$86 - $179 Avg. price/night*
Ollie #14 of 68 hotels in Berkshires
Professional photos | Traveler photos (59)
Special Offer BOOK DIRECT AND SAVE
Blantyre (Lenox) 4.0 of 5
16 Blantyre Rd, Lenox, MA 01240-2776
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$472 - $1,169 Avg. price/night*
Ollie #15 of 68 hotels in Berkshires
#4 of 14 hotels in Lenox
Professional photos | Traveler photos (214)
Willows Motel (Williamstown) 2.0 of 5
480 Main St, Route 2, Williamstown, MA 01267-2609
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$87 - $145 Avg. price/night*
Ollie #16 of 68 hotels in Berkshires
  •  Pleasant stay 
  • Helpful, friendly innkeepers. the location in Williamstown is great... more
  • January 17, 2017
Professional photos | Traveler photos (69)
276 Brodie Mountain Rd, Hancock, MA 01237
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$114 - $191 Avg. price/night*
Ollie #17 of 68 hotels in Berkshires
  •  Spacious Rooms 
  • Very lovely rooms, nicely decorated and spacious. Large indoor pool with... more
  • January 22, 2017
Professional photos | Traveler photos (293)
Yankee Inn (Lenox) 2.5 of 5
461 Pittsfield Rd, Lenox, MA 01240-2132
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$83 - $159 Avg. price/night*
Ollie #18 of 68 hotels in Berkshires
#5 of 14 hotels in Lenox
  •  Very nice hotel 
  • Very nice hotel. You get a good feeling about the Yankee Inn as soon as... more
  • January 17, 2017
Professional photos | Traveler photos (121)
199 Main St, Lee, MA 01238-1660
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$89 - $261 Avg. price/night*
Ollie #19 of 68 hotels in Berkshires
#3 of 9 hotels in Lee
  •  Romantic weekend  
  • Impressive, and my reservations aren't until Valentines weekend. Amber has... more
  • January 20, 2017
Professional photos | Traveler photos (150)
MAPLE TERRACE MOTEL (Williamstown) 2.5 of 5
555 Main St, Williamstown, MA 01267-2612
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$65 - $99 Avg. price/night*
Ollie #20 of 68 hotels in Berkshires
Professional photos | Traveler photos (57)
Special Offer Stay & Ski