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Showing 16-30 of 64 Resorts and Lodges

Chesapeake Inn

Lenox, Massachusetts, United States
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$151

Chesapeake Inn of Lenox in the Berkshires is only one quarter mile from Tanglewood's East Gate and one mile from the center of Lenox. Rooms feature queen sized beds, private baths, central air conditioning, fresh cut flowers. Pampering personal service includes full breakfast, newspapers, after concert snacks. Heated 75' lap pool.... more

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

Berkshire Mountain Lodge

Pittsfield, Massachusetts, United States
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You can find spectacular accommodations at Vacation Village properties across the country, but for a real treat head to Pittsfield, Massachusetts, and the Berkshire Mountain Lodge. Featuring 146 one-bedroom condominiums with great amenities like fully-appointed kitchens, individual living and dining areas, and two HD televisions, you will feel... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 146 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Pittsfield
  • Nearby Water Onota Lake
  • Open Dates All Year

Windflower Inn

Great Barrington, Massachusetts, United States
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$151

The Windflower is a classic New England inn, located on a Berkshire County estate dating back to the 1850's. A full breakfast is served daily along with tea and homemade cookies in the afternoon. All rooms have privatebath, AC and many have a working fireplace. The Inn has its own pool and is directly across from a public golf course. The area... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size N/A
  • Conference Facility
  • Kids Allowed
  • Nearby City Grreat Barrington
  • 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
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$151

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

A B&B in the Berkshires

Richmond, Massachusetts, United States
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 3 units
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Bed & Breakfasts, Inns

Thornewood Inn & Restaurant

Great Barrington, Massachusetts, United States
77
Good
16 Reviews
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$76

The Thornewood Inn, located in the heart of the beautiful Berkshire Hills, is the perfect place to vacation in any season. Conveniently situated at the base of Monument Mountain on five acres, the Inn is adjoined by a state forest and offers walking trails that double as cross country ski trails in winter when mother nature cooperates.... more

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

Orchard Shade

New Marlborough, Massachusetts, United States
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$76

Orchard Shade is a beautiful 1840 house set on ten acres with lovely gardens and a swimming pool. Located in Sheffield, Massachussetts, the oldest town in the Berkshires, the town is noted for its historic homes and is a center for antiquers, with over fifty shops and auctions at the famous Bradford Antique Gallery. Hiking and biking trails and... more

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

The Rookwood Inn

Lenox, Massachusetts, United States
85
Very Good
34 Reviews
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$210

The Rookwood Inn is a restored fairy tale Victorian bed and breakfast in the charming village of Lenox. Peace, seclusion and relaxation are exactly what you will get when you stay at this unique bed and breakfast. Private bathrooms, Wi-Fi, and individual AC are all modern touches that make your stay feel like home. In the morning, a scrumptious... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 19 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Lenox
  • Nearby Water N/A
  • Open Dates All Year
RESORT TYPE(S):
  • Meetings
  • Family
  • Pet Friendly
  • Romantic
  • Wedding

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

Federal House Inn

Lee, Massachusetts, United States
95
Excellent
66 Reviews
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$76

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

Lanesboro Country Inn

Lanesborough, Massachusetts, United States
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$69

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

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

The Cornell In Lenox

Lenox, Massachusetts, United States
90
Excellent
261 Reviews
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$120

The Cornell in Lenox offers peaceful Berkshire vacations with the historic charm of New England. This unique bed & breakfast is composed of three historic buildings, dating back as far as 1777! Each guestroom and suite features period-style d├ęcor, with charming touches like print wallpaper, painted cupboards, vintage toys & four poster... more

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 28 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Pittsfield, MA
  • Nearby Water Stockbridge Bowl
  • Open Dates All Year
RESORT TYPE(S):
  • Family
  • Historical
  • Holiday
  • Nature
  • Romantic

The Orchard Hotel

Williamstown, Massachusetts, United States
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  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 49 units
  • Conference Facility
  • Kids Allowed
  • Nearby City N/A
  • Nearby Water N/A
  • Open Dates All Year

Showing 16-30 of 64 Resorts and Lodges

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