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Showing 16-30 of 67 Resorts and Lodges

Harbour House Inn

Cheshire, Massachusetts, United States
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

White Horse Inn

Pittsfield, Massachusetts, United States
95
Excellent
73 Reviews
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Lanesboro Country Inn

Lanesborough, Massachusetts, United States
$69
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The Lanesboro Country Inn is a wonderfully intimate, centrally located cozy retreat in the heart of the Berkshires. Featuring brand new , individual log cabins, it provides spacious accommodations to help you unwind. Come relax, discover, and enjoy everything the Berkshires have to offer.... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year

Chambery Inn

Lee, Massachusetts, United States
93
Excellent
155 Reviews
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Make your Massachusetts getaway extraordinary at Chambery Inn. In this nineteenth century parochial school turned country inn, you will find nine exceptional rooms French-inspired design and little touches of luxury that will help you relax. Start your day with a charming breakfast basket, delivered right to your door, before venturing out into the... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 9 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Boston
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Family
  • Fishing
  • Golf
  • Luxury
  • Ski/Snowboard

Federal House Inn

Lee, Massachusetts, United States
95
Excellent
66 Reviews
$76
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Soon to be listed on the National Register of Historic Buildings, the Federal House is located in the Berkshires close to summer music, drama and dance festivals. Golf and tennis privileges are available at the Stockbridge Country Club, two miles directly down Main Street and in the winter cross-country and downhill ski areas are nearby.... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City South Lee
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Wyndham Vacation Resorts - Bentley Brook

Hancock, Massachusetts, United States
82
Very Good
36 Reviews
$129
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See the mountainside suspended from a chairlift above Jiminy Peak Mountain and discover an unparalleled vacation destination at Wyndham Bentley Brook! This premier Hancock, MA vacation resort is located at the foot of the ski slopes of Jiminy Peak Mountain Resort. After a full day of skiing, snowboarding, hiking and partaking in other seasonal... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 32 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Hancock
  • Nearby Water Pontoosuc Lake
  • Open Dates All Year
RESORT TYPE(S):
  • Historical
  • Mountain
  • Ski/Snowboard
  • Villas and Condos

The Yankee Suites Extended Stay

Pittsfield, Massachusetts, United States
91
Excellent
7 Reviews
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year

Wheatleigh

Stockbridge, Massachusetts, United States
96
Excellent
19 Reviews
$251
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The perfect marriage of the grandeur of a Florentine palazzo with elegance and comfort of the 21st century. On 22 acres overlooking the Berkshire Mountains and lake, Wheatleigh is two and a half hours by car from New York and Boston, with easy access by private plane. Built in 1893, Wheatleigh has just completed a four-year renovation to create one... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 19 units
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Luxury

The Morgan House Inn

Lee, Massachusetts, United States
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Shaker Mill Inn

West Stockbridge, Massachusetts, United States
$109
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Located in the small, charming Massachusetts town of West Stockbridge, Shaker Mill Inn is a bed and breakfast that offers comfortable, spacious suite-style rooms. And, you guessed it -- breakfast with croissants, turnovers, ham and cheese biscuits, muffin tops, scones, breakfast bars, cinnamon-raisin-walnut buttermilk rolls, delicious quiches, tart... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 9 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Lenox
  • Nearby Water Card Pond
  • Open Dates All Year
RESORT TYPE(S):
  • Honeymoon
  • Romantic
  • Ski/Snowboard

Gateways Inn & Restaurant

Lenox, Massachusetts, United States
93
Excellent
45 Reviews
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Vacation Village at Berkshires

Hancock, Massachusetts, United States
83
Very Good
698 Reviews
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For years, the fortunate have flocked to the Berkshires Vacation Village timeshares to savor the region's incomparable complement of American history, natural beauty, sporting entertainment, and cultural enrichment. Soak in the charm of a bygone era while visiting the grounds and stately homes of legendary American figures. The scenic hills,... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 298 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Hancock
  • Nearby Water Onota Lake
  • Open Dates All Year
RESORT TYPE(S):
  • Historical
  • Luxury
  • Timeshare

Old Inn on the Green

New Marlborough, Massachusetts, United States
80
Very Good
34 Reviews
$151
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The Old Inn on the Green & Gedney Farm are located in the Old Berkshire village of New Marlborough, now a National Historic District. Enjoy the tranquilty and dine in the only restaurant in the Berkshires rated 3 stars by The Boston Globe!... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City New Marlborough
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Berkshire Hills Motel

Williamstown, Massachusetts, United States
85
Very Good
54 Reviews
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year

Showing 16-30 of 67 Resorts and Lodges

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