Chesterfield Bed and Breakfasts

If you're stumped for vacation ideas, consider a trip to a Chesterfield bed and breakfast. This city is located in Massachusetts, just west of Boston. Chesterfield has a...  Read more
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B&Bs in Chesterfield

 
from $95

Chesterfield, MA
Within city limits
Enjoy Simple country elegance..... ...Read more

B&Bs in Towns near Chesterfield

 
 
from $165

South Lee, MA
'Of all the places we have stayed in around the world, your hospitality was the best' Th...Read more
 
 
from $195

Lenox, MA
Fairy-tale Victorian bed & breakfast has the best location in the Berkshires! Comfort...Read more
 
 
from $160

Lee, MA
Centrally located, yet a world apart,set on a 32 acre pastoral meadow, with rolling tapes...Read more
 
from $325

Lenox, MA
110-year-old luxury farmhouse on 10 country acres with magnificent trees, lawns & forest ...Read more
 
from $175

Deerfield, MA
An original New England country inn, nano local Champney's restaurant on site, children w...Read more
 
from $125

Blandford, MA
This beautifully restored 18th-century inn, nestled between the Berkshires and Northampto...Read more
 
from $80

Northampton, MA
Featured in Yankee Magazine's Best of N.E. issue, this is the closest b&b to downtown Nor...Read more
 
from $100

Lenox, MA
One of the first grand Berkshire Cottages, on 27 beautiful acres, centrally located betwe...Read more
 
 
from $115

Greenfield, MA
Nestled in the valley and perched on a hillside sits an oasis of uncommon accommodation. ...Read more
 
from $175

Amherst, MA
A Unique Bed and Breakfast suite in a beautifully renovated 1904 farmhouse in a flower fa...Read more
 
from $229

Lenox, MA
Turn back the clock to the Gilded Age in this 1897 home; an inn since the 1930's. Most ro...Read more
 
from $95

Amherst, MA
1828 restored Amherst homestead. Centrally located for visiting the 5 College in the Pion...Read more
 
from $140

Greenfield, MA
Historic home on the Mohawk Trail on the basalt ridge above the Connecticut River, conven...Read more
 
from $160

Williamsburg, MA
Lovely Gardens, Mountain Views, Private Apartments w/kitchens at this Charming 1790 Organ...Read more
 
from $150

Lee, MA
An 18th century farmhouse comfortably furnished with antiques. A beautiful country setti...Read more
 
 
from $55

Lenox, MA
Twenty-two acre hilltop estate in the Berkshire Mountains of western Massachusetts, acros...Read more
 
from $165

Granby, MA
Beautiful Guest House in the Mount Holyoke Range State Park, near the Notch at Bare Mount...Read more
 
from $100

Whately, MA
A traditional New England Cape Bed and Breakfast home situated next to Whately's beautifu...Read more
 
from $95

Northampton, MA
A nature lover's delight: farmland, forests and a river are right on the property!...Read more
 
 
from $199

Lenox, MA
Beautifully decorated, charming , comfortable & inviting. Lovingly prepared exceptional b...Read more
 
from $185

Amherst, MA
Historic home just a short stroll to the picturesque Amherst Common with its excellent re...Read more