Hillsdale Bed and Breakfasts

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B&Bs in Hillsdale

  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 $175

158 Burt Street, Saugerties, New York
Elegant Catskills Victorian B&B - Culinary Institute of America Chef owned.
  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!
  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 $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 $120

1565 Pleasant Street, South Lee, Massachusetts
Discover the beauty of the seasons in the Berkshire Mountains at this charming inn!
  From $275

2 Kemble Street, Lenox, Massachusetts
The NEW Kemble Inn was purchased by new owners who will modernize and improve this incredible property.
  From $159

15 Hawthorne Street, Lenox, Massachusetts
Victorian graces of the past, all the comforts of today!
  From $170

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

1560 Pleasant Street, South Lee, Massachusetts
'Of all the places we have stayed in around the world, your hospitality was the best' The Gambles Essex, England
  From $200

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 $214

135 Main Street, P.O. Box 52, Lenox, Massachusetts
Tucked away on five breathtaking acres of landscaped gardens - a two minute walk to Lenox Village and only a mile from Tanglewood.
  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.
  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 $109

7 Albany Road, 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 $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 $150

One East Street, Lee, Massachusetts
An 18th century Georgian farmhouse comfortably furnished with antiques. A country setting close to all Berkshire attractions.
  From $165

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

51 Walker Street, Lenox, Massachusetts
The perfect getaway for any occasion!
  From $165

1659 Route 212, Saugerties, New York
Colonial style house, open all year round, just minutes from great skiing, horseback riding, hiking, and shopping.
  From $150

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 $125

17 Main Street, Lenox, Massachusetts
Called 'The Lanai' for its many inviting porches, the Summer White House is an original Berkshire Cottage, built in 1885.
  From $150

20 Broad Street, Kinderhook, New York
1785 Georgian mansion located just 25 minutes from Albany in the quaint countryside town of Kinderhook.
  From $135

69 Maple Avenue, Norfolk, Connecticut
A romantic getaway with a host of site-seeing opportunities awaits you!