TOP 30 Charming inn with history in Massachusetts

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The New Boston Inn is a charming and historic establishment located at 101 North Main Street in the picturesque town of Sandisfield, Massachusetts. This institution offers a unique combination of a bar, restaurant, and lodging, making it the perfect destination for travelers and locals alike. Guests can enjoy delicious meals made with locally-sourced ingredients in the cozy dining room, relax with a drink at the bar, or spend the night in one of the comfortable and beautifully appointed rooms. With its warm hospitality and inviting atmosphere, the New Boston Inn is the ideal spot for a memorable dining and lodging experience in the heart of New England.

The Trainmaster's Inn, located at 1292 South Main Street in Palmer, Massachusetts, offers a unique and high-end lodging experience. From the same team behind The Steaming Tender Restaurant, this inn allows guests to immerse themselves in the architectural beauty of the 19th century while enjoying modern comforts. Guests can choose to stay in the Inn itself or in one of the unique properties offered, such as the 1946 Bangor Aroostook Caboose overlooking the New England Central Railroad Railyard. The caboose has been meticulously restored to maintain its authentic charm.

Publick House Historic Inn is a charming and cozy establishment located at 277 Main Street in Sturbridge, Massachusetts. This historic inn offers a unique combination of food, lodging, and restaurant services, making it the perfect destination for a relaxing getaway or a delicious meal. With its quaint New England charm and warm hospitality, Publick House Historic Inn provides guests with a truly memorable experience. Whether you're looking for a comfortable place to stay, a delectable meal, or a cozy spot to relax, this institution has everything you need for a delightful stay in Sturbridge.

The Old Inn On The Green Restaurant is a charming dining establishment located at 134 Hartsville-New Marlborough Road in New Marlborough, Massachusetts, United States. The dining rooms are beautifully illuminated by candlelight and feature cozy fireplaces in each room. The restaurant boasts an award-winning wine list curated by General Manager Eric Goulange. The decor includes comfortable windsor chairs, mahogany tavern tables, iron chandeliers, and wall sconces that reflect the inn's early history. During the summer months, guests can enjoy dinner on the garden terrace under a white canopy with views of the dome steepled 19th-century Meeting House and the surrounding wooded country road. After dinner, patrons can relax in the taproom with a glass of port or retire to one of the historic bedrooms upstairs for an overnight stay.

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.

The Stockbridge Country Inn is a charming bed and breakfast located at 26 Glendale Road in Stockbridge, Massachusetts. Nestled in the heart of the picturesque Berkshires, this cozy inn offers beautifully appointed guest accommodations, each with its own unique character and style. Guests can enjoy a peaceful and relaxing atmosphere, surrounded by stunning gardens and a cozy fireplace room. Conveniently located just 1 mile away from the Norman Rockwell Museum and Chesterwood, The Stockbridge Country Inn is the #1 closest Berkshires Bed and Breakfast to these popular attractions. This makes it an ideal choice for visitors looking to explore the museum while enjoying the serene surroundings of the Berkshires.

Located at 91 Walker Street in Lenox, Massachusetts, the Hampton Terrace Inn is a historic bed and breakfast that has been rated the #1 place to stay in Lenox on Tripadvisor. Originally built in 1897, this inn was once owned by some of the wealthiest families in the country and was among the first of the "Berkshire cottages" to welcome guests. Today, the inn offers romantic cottages and suites that have been updated with modern amenities while still preserving the property's rich history. Just a 5-minute walk from downtown Lenox, Hampton Terrace Inn is the perfect location for a Berkshires getaway. Guests can enjoy private baths, air conditioning, HDTVs, free Wi-Fi, complimentary cognac and liqueurs, and a full breakfast buffet included in their room rate. The inn also features a heated pool, jetted tubs, and fireplaces for guests to relax and unwind after a day of exploring the Berkshires.

Welcome to Brook Farm Inn, a charming lodging establishment located at 15 Hawthorne Street in Lenox, Massachusetts. Our Victorian Inn offers 15 guest rooms, including a carriage house with three luxury accommodations, perfect for a relaxing getaway in the beautiful Berkshires. Surrounded by trees and award-winning gardens, our inn provides a serene and secluded atmosphere, while still being just a short walk from historic Lenox village. Built in 1882 and furnished with antiques, our elegant inn features a library filled with poetry, history, and literature, where guests can enjoy the soothing sounds of classical music. Each room at Brook Farm Inn includes a full plated breakfast, providing a perfect start to the day before exploring all that the Berkshires have to offer. From skiing and hiking to theater and antiquing, there is something for everyone to enjoy in the area.

Located on the charming Old Main Street in Deerfield, Massachusetts, the Deerfield Inn offers a glimpse into the rich history of colonial America. Surrounded by 18th and 19th-century homes, schools, and farms, our hotel exudes authentic New England charm. Situated in the heart of the best-documented small town in America, our inn invites guests to relax on our front porch and soak in the historic surroundings. Our hotel features a restaurant and tavern with cozy wing chairs, crackling fireplaces, and a warm atmosphere that welcomes travelers seeking a peaceful retreat. Whether you're looking for a relaxing getaway or planning a fairytale wedding in Deerfield, the Deerfield Inn provides the perfect setting for a memorable experience. Come discover the beauty and tranquility of our historic Massachusetts hotel.

The Daniel Stebbins House Inn is a charming lodging located at 25 Woodbridge Street in South Hadley, Massachusetts, United States. This historic inn offers a unique experience with rooms named after significant figures in local history. The Red Room, Blue Room, Cream Room, Green Room, and Royal Room each offer luxury linens, gas fireplaces, private baths, and access to modern amenities such as wireless internet and TV streaming. Guests can enjoy a peaceful stay in this "home away from home" atmosphere, where they can relax in the beautifully landscaped gardens or on the porch. The inn is conveniently located near Mt. Holyoke College and other nearby colleges, as well as the downtown area with restaurants, shops, and entertainment options.

The Allen House Victorian Inn is a charming and historic lodging located at 599 Main Street in Amherst, Massachusetts. This beautifully restored Victorian mansion offers guests a unique and cozy stay in the heart of New England. The inn boasts elegant decor, comfortable accommodations, and warm hospitality. Guests can enjoy a delicious breakfast each morning and relax in the peaceful garden or on the inviting porch. With its convenient location near shops, restaurants, and attractions, the Allen House Victorian Inn is the perfect choice for a memorable stay in Amherst.

The Jenkins Inn is a charming establishment located at 7 West Street in Barre, Massachusetts, offering a unique combination of food, lodging, and restaurant services. This cozy inn provides guests with comfortable accommodations and a warm, inviting atmosphere. The on-site restaurant serves delicious meals made with locally sourced ingredients, ensuring a memorable dining experience. Whether you're looking for a relaxing getaway or a delicious meal, The Jenkins Inn is the perfect destination.

The North Bridge Inn is a charming lodging establishment located at 21 Monument Street in historic Concord, Massachusetts. Nestled in the heart of this picturesque New England town, the inn offers cozy accommodations and a warm, welcoming atmosphere for guests to relax and unwind. With its convenient location near the famous North Bridge, where the first shots of the American Revolutionary War were fired, visitors can explore the rich history of the area and enjoy the beauty of the surrounding nature trails and historic sites. Whether you are looking for a peaceful retreat or a convenient base for exploring all that Concord has to offer, The North Bridge Inn is the perfect choice for your next getaway.

Hawthorne Inn is a charming lodging institution located at 462 Lexington Road in Concord, Massachusetts, United States. Nestled in a picturesque setting, the inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. With its convenient location, guests can easily explore the historic town of Concord and its many attractions. Whether you are visiting for business or pleasure, Hawthorne Inn provides a cozy retreat for a memorable stay.

The Clark Currier Inn is a charming lodging establishment located at 45 Green Street in the historic town of Newburyport, Massachusetts. This beautifully restored inn offers a cozy and welcoming atmosphere for guests looking to experience the rich history and culture of the area. With comfortable accommodations and modern amenities, the Clark Currier Inn is the perfect place to relax and unwind during your visit to the United States.

Located in the charming town of Ipswich, Massachusetts, the Ipswich Inn Bed & Breakfast offers a cozy and inviting stay for guests looking for a relaxing getaway. Situated at 2 East Street, this quaint establishment provides comfortable accommodations with a touch of New England charm. With its convenient location near local attractions such as Crane Beach and the Ipswich River Wildlife Sanctuary, guests can easily explore the beauty of the area. Whether you are visiting for a weekend escape or a romantic retreat, the Ipswich Inn Bed & Breakfast is the perfect choice for a memorable stay in Ipswich.

The Paquachuck Inn, located at 2056 Main Road in Westport, Massachusetts, invites you to experience a historic stay on the coast. Built in 1827 by privateer Issac Cory, this three-story post and beam building once served as a ship chandlery, general store, customs house, and post office. Original artifacts from its maritime past, such as store cabinets and harpoons, can still be found throughout the inn. Situated on Westport Point, with views of the harbor entrance, fishing fleet, and oyster farm, the Paquachuck Inn offers a glimpse into the town's rich history. The name "Paquachuck" comes from the local clam, the quahog, and reflects the area's Native American heritage.

The Inn at Newton Highlands is a charming lodging establishment located at 1170 Walnut Street in Newton, Massachusetts. This cozy inn offers a comfortable and inviting atmosphere for guests looking to relax and unwind in a peaceful setting. The Inn features well-appointed rooms, friendly staff, and convenient amenities to ensure a pleasant stay for visitors. Whether you are traveling for business or leisure, The Inn at Newton Highlands is the perfect choice for a memorable and enjoyable experience in the heart of Newton.

The Salem Inn is a charming lodging establishment located at 7 Summer Street in the historic town of Salem, Massachusetts, United States. This quaint inn offers a cozy and comfortable atmosphere for guests to relax and unwind during their stay. With its convenient location near local attractions such as the Salem Witch Museum and Salem Maritime National Historic Site, The Salem Inn is the perfect choice for travelers looking to explore the rich history and culture of this iconic New England town. Enjoy a peaceful retreat in one of their well-appointed rooms or suites, complete with modern amenities and thoughtful touches to ensure a memorable experience. Experience the warm hospitality and personalized service that The Salem Inn is known for, making it a top choice for visitors seeking a memorable stay in Salem.

A Friendly Inn At Harvard is a charming lodging establishment located at 1673 Cambridge Street in Cambridge, Massachusetts, just a stone's throw away from the prestigious Harvard University. This cozy inn offers comfortable and affordable accommodations with a friendly and welcoming atmosphere. Guests can enjoy a peaceful stay in a convenient location, with easy access to the university campus, as well as nearby attractions and amenities. Whether visiting for business or pleasure, A Friendly Inn At Harvard provides a home away from home for travelers seeking a comfortable and laid-back place to rest and recharge.

The Samuel Sewall Inn is a charming lodging establishment located at 143 Saint Paul Street in Brookline, Massachusetts. This historic inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to experience the rich history and culture of the area. With its convenient location near Boston and its cozy rooms, the Samuel Sewall Inn is the perfect place to stay for both leisure and business travelers. Enjoy a peaceful retreat in this quaint New England inn while exploring all that the vibrant city of Brookline has to offer.

The Stepping Stone Inn is a charming lodging establishment located in the heart of Salem, Massachusetts. Situated at 19 North Washington Square, this historic inn offers a cozy and inviting atmosphere for guests looking to explore the rich history and culture of the area. With comfortable accommodations and personalized service, The Stepping Stone Inn is the perfect home base for visitors looking to experience all that Salem has to offer. Whether you're in town for a weekend getaway or a longer stay, The Stepping Stone Inn is the ideal choice for a memorable and relaxing stay in this picturesque New England town.

Curwen House - The Salem Inn is a charming and historic lodging located in the heart of Salem, Massachusetts. Situated at 331 Essex Street, this institution offers guests a unique and unforgettable experience in a beautiful and well-preserved building. The inn boasts a rich history and a cozy atmosphere, making it the perfect place to stay for those looking to explore the rich culture and heritage of Salem. With comfortable accommodations and top-notch amenities, Curwen House - The Salem Inn is the ideal choice for travelers seeking a memorable and relaxing stay in this historic New England town.

ShoreWay Acres Inn & Cape Cod Lodging is a charming and historic lodging option located at 59 Shore Street in Falmouth, Massachusetts. This family-owned inn offers a unique glimpse into authentic Cape Cod life, past and present, with a focus on preserving history and tradition. The inn started with nine rooms in a historic sea captain's home built in 1806 and has since expanded to offer 70 rooms with modern amenities. Guests can enjoy a variety of accommodations, from traditional rooms to suites and vacation rentals with full kitchens. The inn is located on one of Falmouth's most historic streets, providing a peaceful and residential atmosphere while still being within walking distance to Falmouth Village and Surf Drive Beach. Nearby attractions include Martha's Vineyard ferries, the Shining Sea Bikeway, and day trips to Plymouth, Hyannis, and Provincetown.

Rockmere Inn is a charming lodging establishment located at 2 Mechanic Street in the picturesque town of Marblehead, Massachusetts. Nestled in a historic building, this inn offers a cozy and welcoming atmosphere for guests looking to relax and unwind. The rooms are tastefully decorated and feature modern amenities, while the common areas provide a perfect spot to socialize or enjoy a cup of coffee. With its convenient location near the heart of Marblehead, guests can easily explore the town's shops, restaurants, and attractions. Whether you're visiting for a weekend getaway or a longer stay, Rockmere Inn is the perfect home away from home.

Sea Street Inn is a charming lodging establishment located at 328 Sea Street in Barnstable, Massachusetts, United States. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind by the sea. With its convenient location near the beach and local attractions, Sea Street Inn is the perfect destination for a peaceful getaway on Cape Cod. Enjoy a cozy room, friendly service, and a memorable stay at this quaint seaside retreat.

The Colonial Inn is a charming lodging establishment located at 28 Eastern Point Road in Gloucester, Massachusetts. This historic inn offers a cozy and comfortable stay for guests looking to immerse themselves in the rich history and scenic beauty of New England. With its picturesque location near the coast, guests can enjoy stunning views of the ocean while experiencing the warm hospitality and classic charm of a traditional colonial inn. Whether you are visiting for a weekend getaway or a longer stay, the Colonial Inn provides a peaceful retreat in a quaint and historic setting.

Located at 135 Massachusetts 28 in Yarmouth, Massachusetts, the Tidewater Inn is a charming lodging institution in the heart of Cape Cod. With a prime location minutes away from beaches, boating, fishing, golf, shopping, and family-friendly attractions, guests can enjoy all that the area has to offer. Situated on three and a half acres next to Mill Creek, guests can relax and enjoy the serene surroundings that lead to Lewis Bay and Nantucket Sound. Family-owned for almost half a century, the Tidewater Inn prides itself on hospitality and serving as an ambassador for the Cape Cod community. With a variety of rooms to choose from, guests can find the perfect accommodation for their stay. The on-site Helen's Breakfast Diner offers affordable and delicious grab-and-go options, with outdoor seaside seating available.

The Somerset House Inn is a charming lodging located at 378 Commercial Street in the picturesque town of Provincetown, Massachusetts. This historic inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to enjoy during their stay. With its convenient location near shops, restaurants, and attractions, the Somerset House Inn is the perfect choice for those looking to explore all that Provincetown has to offer. Experience a relaxing getaway at this quaint inn in the heart of Cape Cod.

The Red Inn is a charming lodging establishment located at 15 Commercial Street in the picturesque town of Provincetown, Massachusetts. Situated on the waterfront, this historic inn offers guests a unique and cozy accommodation experience. With stunning views of the harbor and a convenient location near shops, restaurants, and attractions, The Red Inn is the perfect place to stay for a relaxing getaway in Cape Cod. The inn features comfortable rooms, a gourmet restaurant, and welcoming staff who are dedicated to providing exceptional service to all guests. Whether you're looking for a romantic retreat or a family vacation, The Red Inn is sure to exceed your expectations.