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The Berkshires, 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 The Berkshires bed and breakfast lodging and country inns. Search our database of The Berkshires B&B's and you'll find detailed listings, current rates, and special deals for bed and breakfasts in The Berkshires, Massachusetts.


Amenities Matching:  

Summer Sports

Some of us just can't get enough fun in the sun. Luckily, many bed and breakfasts are ideally located to make the most of your summer vacation. Enjoy swimming, tennis, volleyball, beach volleyball, surfing and sailing, water skiing, wind surfing, rollerblading and so much more.



All Great Barrington Massachusetts, Bed and Breakfasts Map it
Thornewood Inn bed and breafast

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.

Windflower Inn bed and breafast

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.

Baldwin Hill Farm B&B bed and breafast

Baldwin Hill Farm B&B

Great Barrington, MA


Rooms: 4
With Private Bath: 2
Rates: 118.00- 175.00 USD
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Victorian farm home on a Berkshire hilltop. Convenient access to all Berkshire attractions. Ideal for all types of vacationers! The perfect country setting.


All Lee Massachusetts, Bed and Breakfasts Map it
Devonfield Country Inn B&B bed and breafast

Devonfield Country Inn B&B

Lee, MA


Rooms: 10
With Private Bath: 10
Rates: 160.00- 375.00 USD
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A gracious English-style country house in the heart of the Berkshires sits on 32 acres only 2 miles from Main Street, Stockbridge, home of the Norman Rockwell Museum. Ideally situated for exploring the rolling tapestry of the Berkshire Hills.

Chambery Inn bed and breafast

Chambery Inn

Lee, MA


Rooms: 9
With Private Bath: 9
Rates: 89.00- 289.00 USD
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Chambery Inn has French-inspired design and nine exceptional rooms. This nineteenth-century parochial school turned country inn possesses a unique character, a truly distinctive landmark in the beautiful Berkshire Hills.

Jonathan Foote 1778 House bed and breafast

Jonathan Foote 1778 House

Lee, MA


Rooms: 5
With Private Bath: 5
Rates: 149.00- 225.00 USD
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Romantic 1778 farmhouse, full of history and charm, provides a country setting that is central to all Berkshire attractions. Fireplaces, antiques, and comfort abound.

Applegate Inn bed and breafast

Applegate Inn

Lee, MA


Rooms: 11
With Private Bath: 11
Rates: 150.00- 385.00 USD
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Applegate Inn, a true Bed and Breakfast, was built in the grand era of the 1920's. Privacy is all yours with our six acres of groomed trails & yard.


All Lenox Massachusetts, Bed and Breakfasts City Guide | Map it
Garden Gables Inn bed and breafast

Garden Gables Inn

Lenox, MA


Rooms: 17
With Private Bath: 17
Rates: 154.00- 498.00 USD
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All the romantic charm of a Berkshire Bed and Breakfast but with four-star amenities! Guests of this historic Inn near Lenox Village & Tanglewood love the private baths/spa robes, spa room, pool, organic & locally sourced food and personal service. Green, eco-friendly.

Summer White House bed and breafast

Summer White House

Lenox, MA


Rooms: 6
With Private Bath: 6
Rates: 160.00- 225.00 USD
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The Summer White House is just a mile from Tanglewood, in the very heart of historic Lenox. Outstanding recreation of an era (1885) in a house built by John Schermerhorn.

Cliffwood Inn bed and breafast

Cliffwood Inn

Lenox, MA


Rooms: 5
With Private Bath: 5
Rates: 118.00- 262.00 USD
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At Cliffwood Inn, you will find that same spirit of welcome and hospitality in the early 1890’s mansion of “belle époque” beauty. Built in the Stanford White style, the Bed and Breakfast features polished, inlaid hardwood floors, high ceilings and spacious rooms.

Stonover Farm B&B bed and breafast

Stonover Farm B&B

Lenox, MA


Rooms: 5
With Private Bath: 5
Rates: 325.00- 575.00 USD
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Stonover Farm is a 110-year-old Berkshire "cottage" which served as farmhouse to the Stonover Estate, and which has been renovated extensively. Luxury accommodations include 3 suites & 2 self-contained cottages.

Brook Farm Inn bed and breafast

Brook Farm Inn

Lenox, MA


Rooms: 15
With Private Bath: 15
Rates: 145.00- 425.00 USD
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Brook Farm Inn is a graceful Victorian, close to Lenox Center and Tanglewood, in the heart of the Berkshires of Western Massachusetts. Nestled in a glen surrounded by trees and gardens with heated outdoor pool, the inn is a 4-season destination.

Rookwood Inn bed and breafast

Rookwood Inn

Lenox, MA


Rooms: 19
With Private Bath: 19
Rates: 175.00- 425.00 USD
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Fairytale Queen Anne Victorian bed & breakfast...perfect for your dream getaway. Antique-filled guest rooms each with private bathroom; comfortable, yet elegant decor; delicious, heart healthy breakfasts. Walk to town, T'wood, & many cultural attractions.

Apple Tree Inn bed and breafast

Apple Tree Inn

Lenox, MA


Rooms: 34
With Private Bath: 34
Rates: 60.00- 400.00 USD
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The Apple Tree Inn sits on a twenty-two acre landscaped hilltop estate in the Berkshire Hills of western Massachusetts. It is across the road from Tanglewood, the summer home of the Boston Symphony.

Birchwood Inn bed and breafast

Birchwood Inn

Lenox, MA


Rooms: 11
With Private Bath: 11
Rates: 155.00- 345.00 USD
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Birchwood Inn Bed and Breakfast, of Lenox, MA, has been welcoming friends, old and new, with warmth and congenial hospitality since 1767. The Inn is renowned for its romantic and comfortable country elegance and memorably decadent breakfasts.

1897 Hampton Terrace B&B bed and breafast

1897 Hampton Terrace B&B

Lenox, MA


Rooms: 14
With Private Bath: 14
Rates: 175.00- 345.00 USD
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1897 in-town Lenox Gilded Age landmark home. An inn since 1937. After staying here, Traditional Home Magazine declared "enjoy Gilded Age glamour and relaxed elegance at one of the East Coast's premier getaway destinations" and "absolutely perfect."

Kemble Inn bed and breafast

Kemble Inn

Lenox, MA


Rooms: 13
With Private Bath: 13
Rates: 155.00- 395.00 USD
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Elegant 1881 Georgian mansion, magnificent mountain views, spacious rooms with private baths, fireplaces, A/C and TV. Many have working marble fireplaces and Jacuzzis. Extended continental breakfast is included.

The Cornell Inn bed and breafast

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.

Walker House bed and breafast

Walker House

Lenox, MA


Rooms: 8
With Private Bath: 8
Rates: 100.00- 230.00 USD
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Peggy & Richard Houdek invite you to share Walker House, their historic Berkshire residence. A landmark in classic American Federal architecture, now in its 3rd decade of welcoming guests.


All New Ashford Massachusetts, Bed and Breakfasts Map it
Berkshires Shirakaba bed and breafast

Berkshires Shirakaba

New Ashford, MA


Rooms: 2
With Private Bath: 2
Rates: 180.00- 230.00 USD
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Come away to the ancient hills and cool forests we call the Berkshires. Breathe our clean air, drink our clear water, toss your head back and see stars as if you'd never seen them before.


All New Marlborough Massachusetts, Bed and Breakfasts Map it
The Old Inn on the Green bed and breafast

The Old Inn on the Green

New Marlborough, MA


Rooms: 11
With Private Bath: 11
Rates: 206.00- 365.00 USD
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The Old Inn, once a stagecoach relay, offers authentically restored guest rooms, fine dining in intimate candlelit dining rooms and seasonal al fresco dining on the canopied garden terrace off the taproom.


All Richmond Massachusetts, Bed and Breakfasts Map it
A B&B in the Berkshires bed and breafast

A B&B in the Berkshires

Richmond, MA


Rooms: 3
With Private Bath: 3
Rates: 125.00- 595.00 USD
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Gracious hosts offer great beds and breakfasts, private baths, hammock in the orchard, rolling lawns and meadows.


All Sheffield Massachusetts, Bed and Breakfasts Map it
Ramblewood Inn bed and breafast

Ramblewood Inn

Sheffield, MA


Rooms: 6
With Private Bath: 4
Rates: 115.00- 225.00 USD
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Nestled among the pines in the foothills of the Berkshire mountains, with a serene, spring-fed lake. Convenient to all the scenic and cultural attractions that make the Berkshires famous. Peaceful and relaxed.

Race Brook Lodge bed and breafast

Race Brook Lodge

Sheffield, MA


Rooms: 32
With Private Bath: 32
Rates: 85.00- 210.00 USD
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Relax - Low keyed, informal rustic retreat, the perfect place to relax in a scenic Berkshire country setting. Hike the trails, wade the brook, swing the hammock, dip in the pool, aaaah.

Staveleigh House bed and breafast

Staveleigh House

Sheffield, MA


Rooms: 7
With Private Bath: 7
Rates: 115.00- 195.00 USD
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Welcome to the Staveleigh House. This handsome colonial and two-story barn resides in historic Sheffield. Originally built in 1817 for Reverend Bradford, this house has stood and watched over generations of Sheffield families.


All South Lee Massachusetts, Bed and Breakfasts Map it
Federal House Inn bed and breafast

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.

Historic Merrell Inn bed and breafast

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.


All Stockbridge Massachusetts, Bed and Breakfasts City Guide | Map it
1862 Seasons on Main bed and breafast

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 breafast

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.


All West Stockbridge Massachusetts, Bed and Breakfasts Map it
Shaker Mill Inn bed and breafast

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.


All Williamstown Massachusetts, Bed and Breakfasts Map it
House On Main Street bed and breafast

House On Main Street

Williamstown, MA


Rooms: 5
With Private Bath: 2
Rates: 90.00- 150.00 USD
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The charm of the Victorian era with the luxury of the 21st century. Nestled in a tree-lined setting, with the convenience of walking to the Clark Art Museum, Williams College, Williamstown Theatre Festival, shopping and dining.

1896 House Country Inn & Motels bed and breafast

1896 House Country Inn & Motels

Williamstown, MA


Rooms: 36
With Private Bath: 36
Rates: 59.00- 289.00 USD
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Historic 1896 landmark Inn in Williamstown, MA in the Berkshires, with six Barnside luxury bed & breakfast Suites, a great pub, and 2 charming motels. Our romantic inn features Jacuzzis for 2, fireplaces, king beds, WiFi, DVDs, and full breakfasts.



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