Chesterfield Bed and Breakfasts

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B&Bs in Chesterfield

  From $70

412 Main Road, Route 143, P.O. Box 352, Chesterfield, Massachusetts
Hot tub and fireplaces! Enjoy Simple country elegance.....

B&Bs in Towns near Chesterfield

  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 $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 $120

1565 Pleasant Street, South Lee, Massachusetts
Discover the beauty of the seasons in the Berkshire Mountains at this charming inn!
  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 $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 $125

2 Old Chester Road, Blandford, Massachusetts
This beautifully restored 18th-century inn, nestled between the Berkshires and Northampton, is the perfect B&B getaway!
  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 $175

108 Old Main Street, Deerfield, Massachusetts
An original New England country inn, nano local Champney's restaurant on site, children welcome, dogs with advance okay. History abounds, and family fun - rafting, farms, hiking, shopping, music.
  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.
 

51 Walker Street, Lenox, Massachusetts
The perfect getaway for any occasion!
  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 $175

649 East Pleasant Street, Amherst, Massachusetts
A Unique Bed and Breakfast suite in a beautifully renovated 1904 farmhouse in a flower farm in Amherst.
  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 $125

60 Masterson Road, Whately, Massachusetts
A bed & breakfast adjacent to Northampton, Deerfield & Amherst!
  From $140

55 Stone Ridge Lane, Greenfield, Massachusetts
Historic home on the Mohawk Trail on the basalt ridge above the Connecticut River, conveniently located to area attractions.
  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 $95

459 South Pleasant Street, Amherst, Massachusetts
1828 restored Amherst homestead. Centrally located for visiting the 5 College in the Pioneer Valley and surrounding areas.
  From $75

599 Main Street, Amherst, Massachusetts
A beautiful inn in the center of many historic sites and activities! Located directly across from Emily Dickinson Homestead. Call 413-253-5000 for reservations!
  From $150

P.O. Box 454, Williamsburg, Massachusetts
Lovely Gardens, Mountain Views, Private Apartments w/kitchens at this Charming 1790 Organic Vegetarian/Vegan B&B Retreat!
  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 $85

106 South Street, Williamsburg, Massachusetts
200 year old colonial farmhouse located on 27 acres, less than 2 miles from the center of the lovely village of Williamsburg.
  From $105

29 Highland Drive, Greenfield, Massachusetts
Nestled in the valley and perched on a hillside sits an oasis of uncommon accommodation.