Sheffield Bed and Breakfasts

  • Enjoy peaceful charm and elegance in a 1906 Georgian style mansion secluded on 12 acres in the heart of the Berkshires.

    The Inn at Stockbridge

  • An 18th century Georgian farmhouse comfortably furnished with antiques. A country setting close to all Berkshire attractions.

    Jonathan Foote 1778 House

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

    Inn at Green River Bed & Breakfast

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

    Applegate Bed & Breakfast

 
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B&Bs in Towns near Sheffield

  From $149

15 Hawthorne Street, Lenox, Massachusetts
Victorian graces of the past, all the comforts of today!
  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 $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 $139

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

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.
  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

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!
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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!
  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 $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.
 

51 Walker Street, Lenox, Massachusetts
The perfect getaway for any occasion!
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5 Greenwood St., Lenox, Massachusetts
  From $225

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 $160

Rte. 7, Box 618, Stockbridge, Massachusetts
Enjoy peaceful charm and elegance in a 1906 Georgian style mansion secluded on 12 acres in the heart of the Berkshires.
  From $175

43 Depot Hill Road, Amenia, New York
Exquisite home located in the stunning and historic Hudson Valley, amidst beautiful horse farms in the Berkshire foothills.
  From $180

3 Gifford Drive, Millbrook, New York
Situated adjacent to the Fountains at Millbrook, the Inn is a serene & intimate retreat just 90 minutes north of Manhattan.
  From $80

123 Main Road, Tyringham, Massachusetts
Located in the heart of Tyringham Valley, Cobble View is a nature lovers dream.
  From $100

64 Walker Street, Lenox, Massachusetts
A landmark in classic American Federal architecture built in 1804.
  From $195

7 Hubbard Street, Lenox, Massachusetts
Warm and welcoming,historic and romantic bed and breakfast inn. Experience comfortable country elegance.
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P.O. Box 1284, Sheffield, Massachusetts