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

 
Starting
at $95

Chesterfield, Massachusetts
Enjoy Simple country elegance..... ...Read more

B&Bs in Towns near Chesterfield

 
 
Starting
at $199

Lenox, Massachusetts
Tucked away on five breathtaking acres of landscaped gardens - a two minute walk to Lenox...Read more
 
Starting
at $325

Lenox, Massachusetts
110-year-old luxury farmhouse on 10 country acres with magnificent trees, lawns & forest ...Read more
 
 
Starting
at $150

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

Lenox, Massachusetts
The perfect getaway for any occasion!...Read more
 
 
Starting
at $195

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

Lee, Massachusetts
Built in the grand era of the 1920's, Applegate is set amid towering pines and manicured ...Read more
 
 
Starting
at $160

Deerfield, Massachusetts
An original New England country inn, nano local Champney's restaurant on site, children w...Read more
 
Starting
at $225

Lee, Massachusetts
Centrally located, yet a world apart,set on a 32 acre pastoral meadow, with rolling tapes...Read more
 
Starting
at $125

Blandford, Massachusetts
This beautifully restored 18th-century inn, nestled between the Berkshires and Northampto...Read more
 
 
Starting
at $55

Lenox, Massachusetts
Twenty-two acre hilltop estate in the Berkshire Mountains of western Massachusetts, acros...Read more
 
 
Starting
at $140

Greenfield, Massachusetts
Historic home on the Mohawk Trail on the basalt ridge above the Connecticut River, conven...Read more
 
Starting
at $150

Williamsburg, Massachusetts
Lovely Gardens, Mountain Views, Private Apartments w/kitchens at this Charming 1790 Organ...Read more
 
Starting
at $105

Greenfield, Massachusetts
Nestled in the valley and perched on a hillside sits an oasis of uncommon accommodation. ...Read more
 
Starting
at $125

Whately, Massachusetts
A bed & breakfast adjacent to Northampton, Deerfield & Amherst!...Read more
 
Starting
at $175

Amherst, Massachusetts
A Unique Bed and Breakfast suite in a beautifully renovated 1904 farmhouse in a flower fa...Read more
 
 
Starting
at $150

Lee, Massachusetts
An 18th century farmhouse comfortably furnished with antiques. A beautiful country setti...Read more
 
Starting
at $100

Lenox, Massachusetts
One of the first grand Berkshire Cottages, on 27 beautiful acres, centrally located betwe...Read more
 
Starting
at $229

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

Amherst, Massachusetts
1828 restored Amherst homestead. Centrally located for visiting the 5 College in the Pion...Read more
 
Starting
at $80

Northampton, Massachusetts
Featured in Yankee Magazine's Best of N.E. issue, this is the closest b&b to downtown Nor...Read more
 
Starting
at $95

Northampton, Massachusetts
A nature lover's delight: farmland, forests and a river are right on the property!...Read more
 
Starting
at $100

Lenox, Massachusetts
A landmark in classic American Federal architecture built in 1804....Read more
 
 
Starting
at $199

Lenox, Massachusetts
Beautifully decorated, charming , comfortable & inviting. Lovingly prepared exceptional b...Read more
 
Starting
at $125

Haydenville, Massachusetts
Voted 'Best in the North'. Step back to a time when life was simplerstill so yet grand!...Read more
 

South Hadley, Massachusetts
A charming Victorian home located across the street from Mount Holyoke College & the Sout...Read more
 
Starting
at $100

Whately, Massachusetts
A traditional New England Cape Bed and Breakfast home situated next to Whately's beautifu...Read more
 
Starting
at $150

Granby, Massachusetts
Beautiful Guest House in the Mount Holyoke Range State Park, near the Notch at Bare Mount...Read more
 
Starting
at $185

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