Windsor Bed and Breakfasts

B&Bs in Towns near Windsor

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  From $149

BROOK FARM INN

15 Hawthorne Street, Lenox, Massachusetts
Victorian graces of the past, all the comforts of today!
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  From $130

GARDEN GABLES INN

135 Main Street, P.O. Box 52, Lenox, Massachusetts
Tucked away on five breathtaking acres of landscaped gardens and only a mile from Tanglewood.
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SEVEN HILLS INN

40 Plunkett Street, Lenox, Massachusetts
One of the first grand Berkshire Cottages, on 27 beautiful acres, centrally located between Boston & New York.
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  From $325

STONOVER FARM BED & BREAKFAST

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.
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The perfect getaway for any occasion!
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  From $150

FLOWER HILL FARM BED & BREAKFAST RETREAT

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

TWIN MAPLES BED & BREAKFAST

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.
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  From $175

HAMPTON TERRACE BED AND BREAKFAST INN

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.
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THE WARFIELD HOUSE INN

200 Warfield Road, Charlemont, Massachusetts
New England family farm tradition on a breathtaking 530 spacious acres overlooking the scenic Mohawk Trail.
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  From $95

BROOKWOOD BED & BREAKFAST

43 Old South Street, Plainfield, Massachusetts
European style Bed & Breakfast in a wooded area on a quiet road, high in the Berkshire Hills of western Massachusetts.
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  From $225

THE SUMMER WHITE HOUSE

17 Main Street, Lenox, Massachusetts
Called 'The Lanai' for its many inviting porches, the Summer White House is an original Berkshire Cottage, built in 1885.
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  From $195

BIRCHWOOD INN

7 Hubbard Street, Lenox, Massachusetts
Warm and welcoming,historic and romantic bed and breakfast inn. Experience comfortable country elegance.
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WHISTLER'S INN

5 Greenwood St., Lenox, Massachusetts
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  From $100

WALKER HOUSE

64 Walker Street, Lenox, Massachusetts
A landmark in classic American Federal architecture built in 1804.
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  From $70

THE SEVEN HEARTHS BED & BREAKFAST

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