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 $325

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

South Lee, Massachusetts
'Of all the places we have stayed in around the world, your hospitality was the best' Th...Read more
 
 
Starting
at $199

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

Lenox, Massachusetts
The perfect getaway for any occasion!...Read more
 
Starting
at $125

Blandford, Massachusetts
This beautifully restored 18th-century inn, nestled between the Berkshires and Northampto...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 $160

Deerfield, Massachusetts
An original New England country inn, nano local Champney's restaurant on site, children w...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 $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 $150

Williamsburg, Massachusetts
Lovely Gardens, Mountain Views, Private Apartments w/kitchens at this Charming 1790 Organ...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 $175

Amherst, Massachusetts
A Unique Bed and Breakfast suite in a beautifully renovated 1904 farmhouse in a flower fa...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

Lee, Massachusetts
An 18th century farmhouse comfortably furnished with antiques. A beautiful country setti...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 $55

Lenox, Massachusetts
Twenty-two acre hilltop estate in the Berkshire Mountains of western Massachusetts, acros...Read more
 
Starting
at $125

Whately, Massachusetts
A bed & breakfast adjacent to Northampton, Deerfield & Amherst!...Read more
 
 
Starting
at $199

Lenox, Massachusetts
Beautifully decorated, charming , comfortable & inviting. Lovingly prepared exceptional b...Read more
 
Starting
at $100

Lenox, Massachusetts
A landmark in classic American Federal architecture built in 1804....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 $185

Amherst, Massachusetts
Historic home just a short stroll to the picturesque Amherst Common with its excellent re...Read more
 
Starting
at $100

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

South Hadley, Massachusetts
A charming Victorian home located across the street from Mount Holyoke College & the Sout...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 $125

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