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Top 10 Massachusetts Bed & Breakfasts
Surrounded by the highlands and valleys of the Berkshires as well as the art and culture thriving amidst the historic and elegant cities of Massachusetts, there isn’t a more romantic and charming place to let go than this New England state. The area is filled with quaint bed and breakfasts eager to reach out a hospitable hand and provide a relaxing Massachusetts vacation. Small villages and towns such as Lenox and Stockbridge are beaming with fine cuisine, antiques, and friendly regulars. Gardens and scenic trails are abundant and waiting for a weary wanderer or quiet ponderer. So, whether you are in need of a quiet retreat or an adventurous outing, the bed and breakfasts of Massachusetts are the perfect places to make your stay.

The Garden Gables Inn

Lenox, Massachusetts

View +1 (888) 243 - 0193

Step through the historic front gate of Garden Gables Inn to a peaceful and serene bed and breakfast experience. From the suites and cottage rooms to the main house, you’ll experience unique and charismatic charm. Wrap yourself in your Anichini Spa Robe and enjoy the warmth radiating from your fireplace or the luscious lawns from your private porch. In true bed and breakfast fashion, each morning will begin with your made to order country breakfast. Sip a cup of custom roast coffee while waiting for your Apple Strudel French Toast or organic eggs, made to your liking. Garden Gables Inn not only provides a quaint and comfortable getaway, you’ll find your days filled with romance. Stroll the beautifully landscaped lawns or ease away all your tensions in the heated Olympic-size pool or Lenox Petit Spa. Take a hike to Lenox village where you’ll find shops and dining rich in culture and distinction, or head to Hilltop Orchards and Furnace Brook Winery for an afternoon of wine tasting amongst the apple trees.


135 Main St., Lenox, MA 01240

Fun facts

Originally a home built in 1780, The Garden Gables was first named “Butternut Cottage” because of the butternut trees that occupied the property. The three steep cross-gables are believed to be a part of the original 1780 structure.

Related Onsite Offerings

All guests are welcome to the complimentary guest pantry. Enjoy fresh-baked chocolate chip cookies and just-plucked apples. There is also a complimentary Afternoon Sherry featuring Furnace Brook Wine.


The Wauwinet

Nantucket, Massachusetts

View +1 (508) 228 - 0145

A Nantucket Vacation is full of sophistication, quaintness, and sentimentality. Few places exemplify these traits better than The Wauwinet. Stacked to the brim with luxury rooms, genial employees, and fun activities, a visit to the Wauwinet is a decision to experience what Nantucket really has to offer.

Whether you’d like to stay in the historic inn, or would prefer a little more privacy at one of four cabins, The Wauwinet and its staff are more than happy to cater to you. All are filled with luxurious room, and full of custom furnishings, Pratesi linens, and wildflowers. Take a quiet walk by the shore, go on a bike tour, or pamper yourself at The Wauwinet’s own Spa by the Sea. Fall asleep in the absolute comfort of your huge feather bed, and when you wake up treat yourself to a hearty breakfast. However you indulge yourself, you’ll be doing it in one of the most beautiful locations (and hotels) in the country. Come and treat yourself!


120 Wauwinet Road, Nantucket, Massachusetts 02584

Total area

Nantucket is 105.3 mi².

Dates and Times

Though closed for the winter, The Wauwinet will reopen on April 21, 2016!


Shaker Mill Inn

West Stockbridge, Massachusetts

View +1 (877) 385 - 2484

On the outskirts of West Stockbridge sits the Shaker Mill Inn, where guests find a wealth of relaxation and romance within the Berkshires. Upon entering, the front yard’s rock garden with blooming, fragrant flowers will lead you into the Inn, where suite style rooms create a charming escape. Each suite is filled with warm and inviting colors that compliment the original artwork created by Berkshire artists. You’ll stay cozy with a private bath, a plush bathrobe, and your delivered breakfast basket overflowing with sweet and savory favorites. The relaxation you’ll feel at Shaker Mill Inn will radiate as you experience the sights and sounds of Stockbridge and the area attractions. On summer nights, the Tanglewood lawn is the favorite place to enjoy an evening picnic to the sounds of the orchestra. The Norman Rockwell Museum is an educational and entertaining experience where you will find countless original works of art. When the snow begins to fall, ski enthusiasts will love the convenience of having four area resorts near by: Butternut, Catamount, Jimmy Peak, and Bousquet. Enjoy the Berkshires at Shaker Mill Inn.


Shaker Mill Inn, 7 Albany Road, West Stockbridge, MA


Looking to escape to the Berkshires for your honeymoon? Shaker Mill Inn has a honeymoon suite that includes a beautiful fireplace and Jacuzzi for two.

Related Onsite Offerings

Shaker Mill Inn is partnered with Energy Rising Massage so you can enjoy a private massage right in your suite. From Swedish and hot stone massages to scrubs and wraps, you'll feel renewed and refreshed!


The Village Inn

Lenox, Massachusetts

View +1 (413) 637 - 0020

Located within the quiet streets of Lenox where quaint shops, craftsmen, and antique stores thrive, you’ll find The Village Inn. Built in 1771, The Village Inn fits the description of this historic New England town. Walk through the doors of The Village Inn to ornately stenciled walls and maple floors complementing the Federal architecture. Each of the 32 rooms have a character of its own and include televisions, private baths, and some include whirlpool tubs and fireplaces. Because The Village Inn is a special part of the village of Lenox, it is only minutes away from the culture and its vibrant atmosphere. View fine art, browse antique shops, and marvel over historic churches. Savor a gourmet meal at a number of charming restaurants including the inn’s Rumplestiltskin's Restaurant. Take in the sights of Lenox’s beautiful homes, lakes, and wooded parks filled with trails for hiking and cross country skiing. Enjoy a historic and luxurious stay at The Village Inn in Lenox!


16 Church, St.Lenox, MA 01240-4810


Through its numerous restorations, The Village Inn has preserved the historic nature of the inn while including modern amenities for their modern guests. But, you will still enjoy original pieces such as antique furniture and the main room's maple floors.

Getting there

From Manhattan (3 hours): Take the Major Deegan Expressway or the Henry Hudson Parkway to the Saw Mill River Parkway, then proceed on the Taconic State Parkway. Take the exit marked "Hillsdale, Claverack, Route 23" and follow Route 23 East to Great Barrington. Turn North on Route 7 and continue through Stockbridge. At the first traffic light past Stockbridge, turn left onto Route 7A into Lenox. From Boston (2 1/2 hours): Take the Massachusetts Turnpike to Exit 2, marked Lee. Follow Route 20 West about 4 miles beyond Lee to the second traffic light. Turn left on to Route 183 into Lenox. From the Hartford/Springfield Area (75 minutes): Go North on Route I-91 to the Massachusetts Turnpike West; then proceed by the directions for traveling from Boston. From Albany (1 hour): Go East on the New York Thruway to the Massachusetts Turnpike Exit 2; then proceed by the directions from Boston. Or take Route 20 all the way from Albany to its intersection with Route 7 in Pittsfield. Follow Route 7 South to Route 7A into Lenox.


The 1896 House

Williamstown, Massachusetts

View +1 (888) 999 - 1896

The stone bridge arcs over the duck pond that leads through watery landscapes and gardens to the doorstep of The 1896 House. Romance meanders along the paths and through the passages of each of the three lodges. The Barnside Luxury Suites create a bed and breakfast experience that won’t be forgotten. Indulge in a country candlelight breakfast and enjoy the tranquil scenes from the wicker furnished porch. Mantled fireplaces, four-post canopied beds, and duel whirlpool tubs soothe every tension, and the hand-chosen antiques and decor of each suite add a special charm. This Northern Berkshire retreat is the perfect stay for enjoying a relaxing and rejuvenating vacation. Countless hiking trails near the inn, such as Sheep Hill or Pine Cobble, provide a scenic setting no matter the season. Guests also enjoy the area’s golf, skiing, art and history museums, theater, and more. A stay at The 1896 House is a touch of culture within a luxury retreat.


Route 7 ~ 910 Cold Spring Road, Williamstown, Massachusetts 01267

Fun facts

Originally a milking barn built in 1896, The 1896 House then became a renowned restaurant in 1939. Due to its popularity, lodging was added in 1951.

Related Onsite Offerings

Located at The 1896 House is The '6 House Pub. Enjoy a savory meal from the comfort of a cozy wing-backed chair!


The Inn at Laurel Lake

Lee, Massachusetts

View +1 (413) 243 - 9749

A charming country atmosphere, fine food, and the bounty of the Berkshires are all at your fingertips at The Inn at Laurel Lake. Each room at the inn has its own unique character. From four-postered canopied beds to detailed wall decor and rich wood floor spanning from room to room, you’ll find your stay to be charming and intimate. Each morning, enjoy an elegant breakfast buffet, and each afternoon, dive into the lake with some swimming, fishing, or kayaking. A stay at The Inn at Laurel Lake brings you close to the art, culture, and beauty of the Berkshires. Take in the lovely sounds of the Boston Symphony Orchestra at Tanglewood. Experience theatre excellence during a show with Shakespeare & Company. Or, learn the story of the Shakers at Hancock Shaker Village. No matter which way you turn, you’ll find an atmosphere of charm during your stay at The Inn at Laurel Lake.


615 Laurel Street, Lee, MA 01238


The population of Lee, Massachusetts is 5,985.

Related Onsite Offerings

The Inn at Laurel Lake includes a music room where guests can enjoy an expansive collection of classical albums!


Taggart House

Stockbridge, Massachusetts

View +1 (800) 918 - 2680

Step back into a refined world of distinct taste and historic charm during your stay at Taggart House. Each room shines with character and is decorated from wall to wall with radiating warmth. Deep-soaking tubs, heated towels, and the romance of a full-course, candlelit breakfast create a purely relaxing experience. Wine and fresh, local cheese are offered each afternoon and pair nicely with the library, flickering fireplace, or a bit of billiards. Taggart House is located within the valley town of Stockbridge, where visitors and residents enjoy the luxuries of impressive art, history, and music. The Tanglewood continues to welcome swarms of audiences to enjoy the Boston Symphony Orchestra. People from all corners revel in the master paintings of Norman Rockwell at The Norman Rockwell Museum. Of course, the beauty of the Berkshires is enough to keep you returning year after year.


No.18 Main Street, Stockbridge, MA 01262

Related activities

Taggart House is happy to host your event. Whether you are looking to celebrate a Berkshire wedding, host a shower, or head a corporate event, Taggart House is ready to help you play host.

Fun facts

Taggart House was built in 1850 and was recently added to the National Register of Historic Places.


Gateways Inn & Restaurant

Lenox, Massachusetts

View +1 (888) 492 - 9466

Unparalleled hospitality, impeccable elegance, and remarkable charm all radiate from the walls of Gateways Inn in the quaint village of Lenox. The 12 guestrooms at Gateways Inn are uniquely characterized by individualized design. The calming hues and decorated furnishings as well as modern amenities create a classical ambiance and the comforting feeling of home. Private baths, plush robes, wireless internet, cable television, and a full breakfast served daily in the dining room or lovely enclosed terrace are only some of the added pleasantries. Because Gateways Inn is located in the hills and valleys of the Berkshires, the possibilities for outdoor adventure are endless. You don’t need to travel far from your guestroom to experience horseback rides through beautifully shaded trails, hot air balloon rides over the cascading landscape, and hiking miles and miles of trails marked by natural wonder. Visitors also take advantage of the topography and area ski resorts as well as the many championship golf courses.


51 Walker Street, Lenox, MA 01240

Getting there

From NYC and points south: Take the Taconic State Parkway North or Route 87 North to I-90 East, the Massachusetts Turnpike, until Exit 2 (Lee). At the end of the ramp, turn right to the town of Lee (Route 20 West). Drive through the town following the signs for Lenox. After a few miles, Route 20 merges with Route 7 North. After the merge stay on the left lane and at the second traffic light, turn left onto Walker Street/Route 183 South and proceed toward the center of town (about 1 mile) where Gateways is on your right. From Boston: Take I-90 West until Exit 2 (Lee). At the end of the ramp, turn right to the town of Lee (Route 20 West). Drive through the town following the signs for Lenox. After a few miles, Route 20 merges with Route 7 North. After the merge stay on the left lane and at the second traffic light, turn left onto Walker Street/Route 183 South and proceed to the center of town (about 1 mile) where Gateways Inn and Restaurant is on your right.

Related Onsite Offerings

Savor a decadent meal at the Restaurant at Gateways Inn. Clean white linens, fresh flowers, and classical music will romance you during your meal. You'll also enjoy the Piano Bar lounge!


Applegate Inn

Lee, Massachusetts

View +1 (800) 691 - 9012

Through the towering gates, gaze beyond the tree-adorned drive to the lush garden meandering through the lawn. You’ll read the doors of Applegate Inn: a treasure from the 19th century that continues to grace guests with a beautiful Berkshire experience. Their 11 rooms create a relaxing and inviting stay with private baths, fireplaces, and spa tubes. The individuality of each room is as special and unique as the gourmet breakfast served each morning in the dining room or porch. The elegance and rejuvenating quality of the inn pours into the yard and surrounding landscape. Applegate’s gardens are a place to let go and escape to a tranquil place. Gaze upon the colors and textures from the porch spanning the entirety of the front of the inn, or sneak a hammock into a private cove. The heated pool is equally soothing and restful. Across the street, Greenock Country Club welcomes you to hit the links, and the inn has bikes and snowshoes ready for an adventure.


279 West Park Street, Lee, Massachusetts 01238


Your gourmet breakfast consists of freshly-squeezed juice, a fruit course, cereal, granola, yogurt, the two hot entrées of the day, muffins fresh from the oven, breads, cheeses, hard-boiled eggs, vegetables, coffees, and teas.

Fun facts

Applegate Inn was built at the end of America's "Gilded Age" and is now a member of the Registry.


The Dan'l Webster Inn & Spa

Sandwich, Massachusetts

View +1 (800) 444 - 3566

Historic hospitality beckons travelers to The Dan'l Webster Inn & Spa. Offering its services for more than three centuries, this Cape Cod landmark has had plenty of time to perfect its craft. Its romantic past interweaves with modern conveniences, creating an intoxicating New England stay. Canopy and four-poster beds harken back to the ornate Victorian era while oversized whirlpool tubs, private balconies, and heated tile floors pamper visitors in the present. The Beach Plum Spa transports you to a world of pure relaxation while wireless internet connections keep you updated on world news. Stroll through the exceptionally manicured lawns, which showcase the beauty of all four seasons. Just off the property, Sandwich and Cape Cod attractions like golf courses, beaches, and bike paths allow you to explore this scenic region. Whether you came for a romantic retreat, business trip, or just a relaxing getaway, The Dan'l Webster delivers an unforgettable stay!


149 Main Street, Sandwich, MA 02563


Your dream wedding comes true with the assistance of the inn's expert planning staff. Elegant banquet rooms, a breathtaking natural setting, and customized wedding packages make your big day everything you ever imagined and more!

Related Onsite Offerings

The Beach Plum Spa rejuvenates your mind, body, and soul with organic body treatments, relaxing massages, soothing facials, and more.