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Plan your fall foliage getaway and head to the Berkshires. More than just western Massachusetts, the Berkshires also encompasses areas of Connecticut, New York and Vermont. The Berkshires offers a wide range of bed & breakfasts, inns, and small hotels. An ideal destination in the autumn months for leaf peeping along country roads, the Berkshires also provides travelers with an abundance of outdoor activities as well as restaurants, galleries, shops and museums.
Escape to a bed and breakfast and enjoy autumn in the Berkshires.
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Brook Farm Inn
Lenox, MA |
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Welcoming to the charming Alexandra Inn Bed & Breakfast, this 1859 southern Vermont bed and breakfast is the perfect relaxing retreat for any getaway. Located only two miles from downtown Bennington, you can enjoy the rich Revolutionary War history or just the natural beauty that Vermont has to offer. more...
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3 room(s)
2 suite(s)
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$99-$179
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1857 Vermont Bed and Breakfast nestled in charming North Bennington Village - an easy walk to restaurants, waterfalls & Bennington College. more...
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In the heat of Bennington The Four Chimneys Inn Bed & Breakfast is a perfect launch pad for day trips to nearby Saratoga Springs NY, Williamstown MA, Lenox MA, and other picturesque destinations. With only eleven beautifully and uniquely appointed guest rooms, the inn has an intimate, yet grand feel that is reminiscent of the graceful summer homes of days gone by. more...
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3 cottage(s)
9 room(s)
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$80-$195
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Rooms, cottage, and suites within walking distance to the many distinctive shops and restaurants. more...
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9 room(s)
1 suite(s)
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$125-$265
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Welcome to the Historic South Shire Inn, situated in the heart of Bennington, VT. This inn has the old world charm of a true bed and breakfast with nine spacious and individually decorated guest rooms. Explore Old Bennington with many historic sites, great restaurants and numerous activities. Visit us soon! more...
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2 room(s)
2 suite(s)
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$80-$150
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If your looking for a place to escape from the daily stress in your life and just want to relax. Well you've come to the right place. Melodys Place offers the pleasures of home and ammenitys you would expect in a vacation full of relaxation and adventure. So the next time your in the area drop us a line and come enjoy the berkshires at Melodys Place. more...
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The Warfield House Inn is a bed and breakfast located in The Valley View Farm in Charlemont, Massachusetts. Overlooking the Mohawk Trail and the Berkshires, this bed and breakfast is complete with two main houses, an on-site restaurant, a special events and wedding facility, and an on-site pub. more...
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9 room(s)
3 suite(s)
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$85-$205
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Voted Central Berkshire County's Best Bed and Breakfast Inn, The Dalton House is centrally located in the small residential town in the heart of the Berkshires. The perfect setting to experience the spectacular beauty of year round outdoor activities. more...
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Historic 1863 farmhouse Colonial, quiet location, stroll to town, pretty, comfy, old New England more...
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Welcome to Berkshire-Pied-a-Terre, vacation rental apartments with bed and breakfast ambiance in Great Barrington, Massachusetts in the southern Berkshires. Stay for a week or enjoy the comfort of a Great Barrington extended stay! more...
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Our lodging site is ideally located only 3 minutes from Great Barrington shopping and restaurants; visitors to the Acorn's Hope Bed and Breakfast Inn in Great Barrington, Massachusetts, have easy access to all the activities and cultural events that the Berkshires have to offer. more...
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13 room(s)
2 suite(s)
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$155-$315
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The Thornewood Inn & Spencer’s Restaurant is located in Great Barrington, MA. The Thorne family invites you to visit our exceptional turn of the century Dutch colonial inn located in the heart of the beautiful Berkshire Hills. Our family run inn offers the best of everything. more...
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The Inn at Green River Bed & Breakfast is an upscale lodging accommodation in Hillsdale, NY nestled in a beautiful rural setting in Columbia County, Hudson River Valley, close to the Berkshires & Tanglewood. Guests return to the inn year after year to, drawn by the Inn's casual elegance, its beautiful, tranquil setting and by innkeeper Deborah Bowen's warm hospitality and scrumptious breakfasts. more...
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The Bell House Bed and Breakfast, open year round, is located in Columbia County, New York, in the historic Hudson Valley. Overlooking beautiful perennial gardens, mature plantings and stately trees, guests can enjoy the swimming pool on a hot summer day or relax on the covered wrap-around porch or the brick terrace overlooking the garden. more...
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Be warmly welcomed and fed like royalty at this beautiful Southern Berkshires B and B. 4 rooms, all with private baths. more...
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We offer fine accommodations in varying degrees of charm and amenities. You'll love our front porch and the meditation garden in the back yard after a long day of touring Hudson, New York, and its great antique centers and mansions. more...
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Located in the heart of New York's Hudson Valley halfway between Manhattan, NY and the Adirondacks. more...
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3 room(s)
4 suite(s)
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$195-$395
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Enjoy the comfort of Mount Merino Manor Bed & Breakfast in a private country setting perfect for romantic getaways, girlfriend’s getaways and single travelers. Easily accessible from the Taconic State Parkway and the NY Thruway and just two hours from Manhattan, three hours from Boston and five minutes to everything happening in Hudson. more...
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4 room(s)
3 suite(s)
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$100-$300
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The Bungalow Hudson Bed & Breakfast is a real arts and crafts bungalow amid the magic of Hudson, New York where you will enjoy style, convenience and simplicity. more...
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The Inn at Hudson Bed & Breakfast, located in Hudson New York, offers three large guest rooms each with a separate bath and furnished by some of Hudson’s antique dealer’s. The Inn is within easy walking distance of several excellent restaurants, as well as Warren Street's renowned stretch of shops and landmark civic buildings. more...
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1 apartment(s)
3 room(s)
2 suite(s)
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$90-$200
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Great Lodging in Columbia County's Hudson River Valley - one block to Historic Hudson's shopping and fine restaurants. more...
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Just 25 minutes from Albany in the Capital Saratoga region of New York, the Van Schaack House Bed & Breakfast offers an elegant escape. The Van Schaack House offers four elegant accommodations for those visiting the Hudson River Valley of New York. We're minutes away from numerous antiques shops, theatre, ballet, pro and college sports and the city's active nightlife. more...
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1 cottage(s)
6 room(s)
3 suite(s)
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Nestled in the beautiful hills of the Berkshires in the charming town of Lee, Massachusetts, Devonfield Bed & Breakfast is an exquisite country inn that offers warm and welcoming hospitality. more...
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Elegant yet comfortable, The Applegate Inn Bed & Breakfast country estate is in the heart of the Berkshires, near horse farms, and only a half mile walk to downtown Lee. Applegate is located in Lee, near Stockbridge (2 miles), Lenox (from Lee to Tanglewood there is a short cut that has no traffic) and Great Barrington. more...
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While vacationing in the Berkshires, step back into a quieter, more relaxed time... with all the modern conveniences more...
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The Chambery Inn Bed and Breakfast, located in Lee, Massachusetts is an old French design parochial school turned Bed and Breakfast that provides a one of a kind atmosphere to the lovely Berkshire horizon. more...
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The Federal House Inn Bed & Breakfast of South Lee, Massachusetts is ideally located in the beautiful Berkshires of Western Massachusetts at the base of Beartown Mountain State Forest. Visit our website & you will choose us! more...
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5 room(s)
2 suite(s)
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$150-$225
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Jonathan Foote 1778 House Bed & Breakfast welcomes you to a historic country inn in Lee, MA, full of warmth and charm that welcomes you to step back in time. We are centrally located near Stockbridge, Lenox, and all the cultural and outdoor Berkshire attractions. more...
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1 block from Lee’s Main Street, minutes from many cultural and sports attractions, 1 mile from Exit 2 Mass Pike. more...
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The Apple Tree Inn Bed and Breakfast in Lenox, MA perches on a twenty-two acre hilltop estate in the Berkshire Mountains of western Massachusetts. The main house dates from 1885 and has had several additions over the years.
more...
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11 room(s)
4 suite(s)
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$180-$345
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Elegantly comfortable Lenox, MA bed and breakfast in the heart of the Berkshires more...
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15 room(s)
1 suite(s)
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$149-$425
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There is poetry here! Brook Farm Inn Bed & Breakfast is a delightfully romantic Victorian inn, in the heart of the Berkshires. Located a short walk from Lenox center, Brook Farm Inn provides an excellent home base for enjoying all the cultural and outdoor offerings of the Berkshires. more...
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A beautiful Lenox inn located in the heart of historic Lenox village, the Cornell Inn Bed & Breakfast is just up the road from Tanglewood. A three-guesthouse Inn, our buildings date back to 1777. more...
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12 room(s)
1 suite(s)
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$100-$425
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In the heart of Lenox, Massachusetts, you will discover Gateways Inn & Restaurant. Offering recently restored rooms and endless attractions, it’s the perfect getaway for any vacation. more...
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11 room(s)
1 suite(s)
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$140-$240
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Getaway to Lenox, MA in the Berkshires to a B&B rich in history. Lenox Massachusetts is home of the Hampton Terrace Bed & Breakfast. We offer divine lodging in Massachusetts. Enjoy the Tanglewood Music Festival. more...
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11 room(s)
1 suite(s)
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$140-$240
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One of Berkshire County’s oldest bed & breakfast inns, completely renovated and featuring a 1930s decor. more...
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Harrison House is a conveniently located on the crest of a hill overlooking Tanglewood and Lenox. Perfect for hikers, cross-country skiers and art lovers. more...
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Welcome to The "NEW" Kemble Inn! In June 2010, this landmark property within walking distance to all the shops and restaurant, was purchased by new owners who will modernize and improve this incredible property. more...
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44 room(s)
4 suite(s)
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$125-$295
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The Seven Hills Inn, one of the original Berkshire gilded age mansions, is set on 27 acres of sweeping lawns and gardens. The Manor House at the inn features 11 bedrooms and is furnished with antiques, hand carved fireplaces and leaded glass windows. This beautiful property is located next door to Edith Wharton’s The Mount and Shakespeare & Company. It is close to Tanglewood and Jacob's Pillow. The property also features rooms in its Carriage House and its Terrace Country Motel. more...
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2 cottage(s)
6 room(s)
3 suite(s)
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$325-$575
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Welcome to Stoneover Farm; a fully appointed luxury Bed & Breakfast located on 10 acres in Lenox just a short walk from Tanglewood, MA. Walking or running on Under Mountain Road is a local pastime, and there are many nearby biking and hiking trails, and Pleasant Valley. more...
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4 cottage(s)
9 room(s)
2 suite(s)
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$270-$515
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TOP-RATED on tripadvisor.com by guests who appreciate the Inn's simple, yet elegant, decor; 4-star amenities; private dining and enviable location on 5 private acres in beautiful Lenox Village. more...
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14 room(s)
5 suite(s)
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$175-$395
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Where memories are made. more...
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The Summer White House Bed & Breakfast is just a mile from Tanglewood, in the very heart of historic Lenox, MA. With many of the Berkshire's finest restaurants and specialty shops within walking distance from our property, and with the Norman Rockwell Museum and The Berkshire Theatre Festival within close proximity, your visit to the Berkshires will be comfortable and complete! more...
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Come join us during any of our four beautiful seasons and share warmth, friendliness and gracious hospitality. more...
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Welcome to the Walker House B&B -- the perfect location for your getaway days and for holidays, family reunions and weddings. The bed & breakfast is located near the center of the charming New England village of Lenox, MA. more...
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Whistler’s Inn - featured on The Travel Channel, is a 1820 English Tudor manor house that overlooks the beautiful Berkshires Mountains of Massachusetts, a charming country inn on 7 acres of gardens, lawns and woodlands that captures the warmth, elegance and romance of a by-gone era. Only a short walk to town or to old Indian trails, guests will find a large variety of country shops, galleries and restaurants affording quiet, personal, unaffected service and charm. more...
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The Old Inn on the Green is nestled in the old Berkshire village of New Marlborough, MA, surrounded by meadows and rolling fields. It features guest rooms with updated amenities and intimate fine dinning provided by candle lit dinning rooms. more...
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A year-round haven of serenity and beauty and home to a variety of formal and informal musical events. more...
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The Thaddeus Clapp House, located in the heart of Berkshire County offers unique New England lodging, and is convenient to all the celebrated attractions. Lenox, Great Barrington, Stockbridge and Williamstown are a short drive. On the National Register of Historic Places with modern conveniences. more...
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3 cottage(s)
2 room(s)
4 suite(s)
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$160-$380
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A Relaxing and Gracious Four Season Country Inn ... The Inn at Richmond is in Richmond, MA provides luxurious Bed and Breakfast Lodging in a pre-Revolutionary War New England colonial home that has been sensitively renovated to retain its historic architectural charm. more...
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Welcome to the Staveleigh House bed and breakfast. This handsome colonial and two-story inn located in historic Sheffield, Massachusetts near the lovely Berkshires offers spacious guestrooms with king and queen beds, private baths, and full gourmet breakfasts. more...
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The Egremont Inn Bed & Breakfast is listed in the National Register of Historic Places, located in the heart of the Southern Berkshires. more...
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10 room(s)
1 suite(s)
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$100-$295
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Discover the magic of the Berkshires at the Historic Merrell Inn Bed & Breakfast located in Lee, MA. Whether it's glorious countryside that interests you or the Berkshires' famous culture, we're an ideal tour base. more...
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1 apartment(s)
8 room(s)
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$120-$325
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Conroy's Bed & Breakfast, located in Stockbridge, Massachusetts is an 1828 farm house built in the Federal style. It sits on three beautiful acres protected by a giant pine hedge. With its canopy of mature maple trees, it provides a shady sanctuary where you can relax with a good book. more...
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8 room(s)
8 suite(s)
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$160-$385
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Welcome to the Inn at Stockbridge Bed and Breakfast of Stockbridge, MA. Enjoy peaceful charm & elegance on twelve secluded acres in the heart of the Berkshires. Every season is stamped with its own beauty and charm! more...
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Berkshires Bed & Breakfast offering friendly hospitality, comfortable accommodations, reasonable rates on a quiet portion of Main Street, next to the Stockbridge Golf Club, and with distant views of Monument Mountain. more...
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We welcome you to the Taggart House, located in Stockbridge, MA in the heart of the Berkshires and close to all that the area has to offer. more...
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8 room(s)
2 suite(s)
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$109-$289
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Conveniently located in the central Berkshires near Lenox, and Stockbridge, The Shaker Mill Inn Bed & Breakfast offers cozy bed & breakfast rooms with king and queen beds, private baths and some with a private deck or Jacuzzi. Business travelers find convenience in our suites that include your own living room for meetings or entertaining clients. We are only a short drive to downhill or cross country skiing at Butternut, Catamount, Jimminy Peak and Bosquet. For summer lodging, Shaker Mill Inn is 5 minutes from the Tanglewood Main Gate and Stockbridge and Lenox Theaters. more...
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A charming colonial inn offering comfortable lodging in warm informal surroundings. more...
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The 1896 House Inn and Country Lodgings is on the scenic route entering Williamstown, Massachusetts in the beautiful Berkshires and the perfect location from which to tour the Southern Vermont and Berkshire Hills. The property has an upscale three building lodging, one of which is the elegant bed and breakfast, Barnside Luxury Suites.
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