Stockbridge, Massachusetts and Surrounding Area - Bed and Breakfast Inns

For over 20 years, Pamela Lanier's Travel Guides have been the savvy travelers' key to great deals on quality, romantic Stockbridge, Massachusetts bed and breakfast lodging and country inns. Search our database of Stockbridge B&Bs and you'll find detailed listings, current rates, and special deals for bed and breakfasts in Stockbridge, Massachusetts.

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  Stockbridge, MA Nearby Cities:
bed and breakfastSouth Lee2 mi
bed and breakfastHousatonic3.1 mi
bed and breakfastLee4.6 mi
bed and breakfastWest Stockbridge4.8 mi
bed and breakfastLenox6.1 mi
bed and breakfastGreat Barrington6.4 mi
bed and breakfastRichmond6.9 mi
bed and breakfastCanaan, NY10.2 mi
bed and breakfastNew Marlborough12.3 mi
bed and breakfastSheffield12.9 mi
bed and breakfastEast Chatham, NY13.5 mi
bed and breakfastHillsdale, NY13.5 mi
bed and breakfastSouth Egremont14.5 mi
bed and breakfastStephentown, NY17.4 mi
bed and breakfastSalisbury, CT20.2 mi
* mileage estimated as the crow flies
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Stockbridge B&B Deals and Specials
Bed and Breakfast Specials in Stockbridge - Special Discounts.Special Discounts 

  Stockbridge Massachusetts, Bed and Breakfasts City Guide | Map it
Stockbridge Country Inn - Bed and Breakfast

Stockbridge Country Inn

Stockbridge, MA


Rooms: 8
With Private Bath: 8
Rates: 149.00- 499.00 USD
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Closest Inn to Norman Rockwell Museum, Chesterwood, and Berkshire Botanical Gardens. Federal-style house with up-country furnishings and Audubon’s. Poster beds, private baths, full breakfast. Minutes to Tanglewood and skiing. Four acres and a pool.

The Inn at Stockbridge - Bed and Breakfast

The Inn at Stockbridge

Stockbridge, MA


Rooms: 16
With Private Bath: 16
Rates: 160.00- 375.00 USD
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Experience peaceful charm and elegance in a 1906 Georgian style mansion secluded on 12 acres. Sixteen well appointed guestrooms, many with a fireplace, double whirlpool and wonderful amenities. Let the cares of the world drift away

1862 Seasons on Main - Bed and Breakfast

1862 Seasons on Main

Stockbridge, MA


Rooms: 5
With Private Bath: 5
Rates: 135.00- 330.00 USD
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An award winning Inn with unparalleled service, gourmet breakfasts, Frette linens, a business center & WiFi. Bike or walk to Stockbridge shops, restaurants, galleries, theater and museums. Just five minutes to Tanglewood.

Conroy’s B&B - Bed and Breakfast

Conroy’s B&B

Stockbridge, MA


Rooms: 9
With Private Bath: 6
Rates: 120.00- 325.00 USD
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Conroy’s Bed and Breakfast, an 1828 farmhouse in the Federal style, sits on three beautiful acres protected by a giant pine hedge. The wide lawn with mature maple trees, wonderful stone walls, old farm foundations and perennial gardens provide four season beauty.

Windflower Inn - Bed and Breakfast

Windflower Inn

Great Barrington, MA


Rooms: 13
With Private Bath: 13
Rates: 100.00- 250.00 USD
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Elegant, small country Inn. Beautiful rooms, some with fireplaces, all with private bath & A/C. Full breakfast with homemade breads, eggs & dairy from local farms, and afternoon tea. Ten acres of grounds & gardens. Family owned & operated for 28 years.

Thornewood Inn - Bed and Breakfast

Thornewood Inn

Great Barrington, MA


Rooms: 15
With Private Bath: 15
Rates: 115.00- 295.00 USD
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Exceptional turn of the century Dutch Colonial Inn set in the heart of the Berkshire Hills. Beautiful antique-appointed rooms, views, Jacuzzis, fireplaces, outdoor pool and in-house massage. Specializing in weddings. Near all attractions.


The Cornell Inn - Bed and Breakfast

The Cornell Inn

Lenox, MA


Rooms: 30
With Private Bath: 30
Rates: 70.00- 400.00 USD
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Our three, uniquely-styled guest houses feature furnishings in Victorian, country and colonial décor. Choose a cozy bedroom, a fully equipped suite with fireplace and kitchen or a room featuring a four-poster bed with fireplace and Jacuzzi.


Historic Merrell Inn - Bed and Breakfast

Historic Merrell Inn

South Lee, MA


Rooms: 10
With Private Bath: 10
Rates: 110.00- 295.00 USD
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One of New England’s most historic stage coach Inns, a few miles from Norman Rockwell Museum and Stockbridge. The only Inn included in the Historic American Buildings Survey.

Federal House Inn - Bed and Breakfast

Federal House Inn

South Lee, MA


Rooms: 9
With Private Bath: 9
Rates: 150.00- 275.00 USD
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Federal House Inn is an historic 1824 Federal Style home with gracious common areas and sunny guestrooms all with private baths and fireplaces. A mile from Stockbridge, minutes to Tanglewood, this elegant Bed and Breakfast is known for its warm hospitality.


Shaker Mill Inn - Bed and Breakfast

Shaker Mill Inn

West Stockbridge, MA


Rooms: 9
With Private Bath: 9
Rates: 99.00- 458.00 USD
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Welcome to our cozy bed and breakfast inn, a Stockbridge and Lenox Massachusetts area lodging nestled in the beautiful Berkshires. The Shaker Mill Inn offers luxurious efficiency suite lodging at affordable prices.

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