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More listings in Sheffield, Massachusetts


Sheffield, Massachusetts

This handsome colonial with original two-story barn resides in historic Sheffield. Originally built in 1817 for Reverend Bradford, this house has stood and watched over generations of Sheffield families.

Guest rooms are appointed with period furnishings, and come with a twin, queen, or king-size bed. 7 rooms with private bath. Sleeps 14-16.

Innkeeper Ali Winston serves a memorable breakfast that might include apple-cheddar quiche, Belgian waffles, pumpkin bread, or baked rhubarb jam. Tea and cookies or cakes are served in the afternoons in the common room or outside under the trees.

Further information on our Pet Friendly Bed & Breakfast Inn Sheffield Berkshires MA

Pet Policy:

  • Our pet friendly Berkshires B&B offers two rooms, #6 and #7, for those travelling with their four-legged friends. Our two pet friendly Berkshires guest rooms with private entrances open out onto the porch to easily allow your four-legged companion to run around and play outdoors.
  • If left alone in the room pets should be crated.
  • We have built a large fenced in area for the dogs so they can run off leash!
  • $25 pet fee per stay, per pet.


Delicious homemade cookies and apple cider, a pot of tea are served when our guests arrive. Robes and early morning coffee (for those early morning walks with your dog!). Laundry service available. Wireless Internet.


Sheffield offers and abundance of fine antiquing, the oldest covered bridge in Massachusetts and Bartholomews Cobble - a 170 acre wildlife preserve.

Our home is conveniently located to Tanglewood, Jacobs Pillow, Barrington Stage Company, Berkshire Theatre Festival, Chesterwood and the Norman Rockwell Museum. Winter finds downhill (Butternut Basin & Catamount) and cross country skiing within minutes of the Inn.

We are also within a short distance of Berkshire School & Simons Rock of Bard College.


Memorial Day - October 31: $145.00-$175, mid week stays are discounted.

We serve a fabulous breakfast! Apple Cheddar Quiche with herb roasted potatoes, Omeletes with smoked Gouda roasted peppers and tomatoes from the garden, Apple brown butter cakes with Berkshire maple syrup! We use our own organic eggs from our happy cage free chickens. Visit them in the barn and meet our goats Santo and Mr. Frodo and our sweet miniature horse Isabelle.

November - April 31st: $125-$150.00. Ski packages offered.

Children are welcome. All rates include a full breakfast, are per night and do not include tax. Rooms are air conditioned during the summer months. Additional $25. charge for rollaway cots.

Dates Available:

Year round.

Minimum Stay:

All weekends from July - October require a two night minimum stay.

Payment Policies:

We receive one nights deposit for a two night stay & 50% on longer stays. Cancelations received two weeks prior to arrival date are refundable less a $20 administration fee. Cancelations received within the two wekk period are non-refundable. All major credit cards accepted.


No smoking. Children are welcome. Dogs must be quiet, well mannered kind, well traveled human types, (no arguing with your master).


Staveleigh House Bed & Breakfast
59 Main St.
Sheffield, Massachusetts 01257
Phone: 413-229-2129
Phone (Toll-free): 1-800-980-2129
Website: Click Here