Hillsdale Bed and Breakfasts

  • One of the first grand Berkshire Cottages, on 27 beautiful acres, centrally located between Boston & New York.

    Seven Hills Inn

  • 110-year-old luxury farmhouse on 10 country acres with magnificent trees, lawns & forest - close to Tanglewood and Lenox.

    Stonover Farm Bed & Breakfast

  • Built in the grand era of the 1920's, Applegate is set amid towering pines and manicured lawns.

    Applegate Bed & Breakfast

  • Elegant 1830 inn offering upscale lodging in a peaceful, relaxing, rural setting - 7 romantic rooms - fireplaces & whirlpools

    Inn at Green River Bed & Breakfast

 
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B&Bs in Hillsdale

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  From $139

9 Nobletown Road, Hillsdale, New York
Elegant 1830 inn offering upscale lodging in a peaceful, relaxing, rural setting - 7 romantic rooms - fireplaces & whirlpools

B&Bs in Towns near Hillsdale

  From $150

27 Barclay Street, Saugerties, New York
Grand Southern Style 1812 Mansion on five lush green acres offering spectacular Hudson River views.
  From $150

One East Street, Lee, Massachusetts
An 18th century Georgian farmhouse comfortably furnished with antiques. A country setting close to all Berkshire attractions.
  From $149

15 Hawthorne Street, Lenox, Massachusetts
Victorian graces of the past, all the comforts of today!
  From $150

279 West Park Street, Lee, Massachusetts
Built in the grand era of the 1920's, Applegate is set amid towering pines and manicured lawns.
  From $100

1565 Pleasant Street, South Lee, Massachusetts
Discover the beauty of the seasons in the Berkshire Mountains at this charming inn!
  From $175

158 Burt Street, Saugerties, New York
Elegant Catskills Victorian B&B - Culinary Institute of America Chef owned.
  From $165

85 Stockbridge Rd., Lee, Massachusetts
Centrally located, yet a world apart,set on a 32 acre pastoral meadow, with rolling tapestry of the Berkshire Hills beyond.
  From $130

135 Main Street, P.O. Box 52, Lenox, Massachusetts
Tucked away on five breathtaking acres of landscaped gardens and only a mile from Tanglewood.
  From $150

1560 Pleasant Street, Stockbridge, Massachusetts
'Of all the places we have stayed in around the world, your hospitality was the best' The Gambles Essex, England
  From $99

325 North Plain Road, Route 41, Great Barrington, Massachusetts
An authentic New England country cottage farmhouse in the heart of the Berkshires & Norman Rockwell country.
  From $100

40 Plunkett Street, Lenox, Massachusetts
One of the first grand Berkshire Cottages, on 27 beautiful acres, centrally located between Boston & New York.
  From $150

7571 Old Post Road, Red Hook, New York
Escape to another century and spend the night in Victorian elegance!
  From $325

169 Under Mountain Road, Lenox, Massachusetts
110-year-old luxury farmhouse on 10 country acres with magnificent trees, lawns & forest - close to Tanglewood and Lenox.
  From $55

10 Richmond Mountain Road, Across from the West Gate at Tanglewood, Lenox, Massachusetts
Twenty-two acre hilltop estate in the Berkshire Mountains of western Massachusetts, across the road from Tanglewood.
  From $160

567 Ackert Hook Road, Rhinebeck, New York
Country retreat on 3 acres in the scenic Primrose Hill are of Rhinebeck. Conveniently located to many area attractions.
  From $175

3244 Sharon Turnpike, Millbrook, New York
This 1808 Colonial sits in park-like grounds on the edge of a Hudson Valley village in Dutchess County's horse country.
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  From $185

11 Old Stockbridge Road, P.o. Box 1717, Lenox, Massachusetts
Fairy-tale Victorian bed & breakfast has the best location in the Berkshires! Comfort & convenience!
 

340 Wurtemburg Road, Rhinebeck, New York
Historic Farmhouse located 3 1/2 miles from Rhinebeck, ideally located to enjoy the highlights of the Hudson River Valley.
  From $109

2 Oak Street, Village Center, West Stockbridge, Massachusetts
Spacious rooms, kitchenettes, private baths, & all the comforts of home. A quiet getaway in the heart of the Berkshires!
  From $105

325 North Plain Road, Route 41, Great Barrington, Massachusetts
An authentic New England country cottage farmhouse in the heart of the Berkshires & Norman Rockwell country.
  From $175

91 Walker Street, Lenox, Massachusetts
Turn back the clock to the Gilded Age in this 1897 home - an inn since the 1930s! Most rooms feature fireplaces & Jacuzzis.
 

51 Walker Street, Lenox, Massachusetts
The perfect getaway for any occasion!
  From $195

7 Hubbard Street, Lenox, Massachusetts
Warm and welcoming,historic and romantic bed and breakfast inn. Experience comfortable country elegance.
  From $100

64 Walker Street, Lenox, Massachusetts
A landmark in classic American Federal architecture built in 1804.