TOP 30 Charming guesthouse in Massachusetts

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1830 Quince Tree House is a charming lodging establishment located at 164 Main Street in the picturesque town of Sandwich, Massachusetts. This historic house offers a cozy and inviting atmosphere for guests looking for a peaceful retreat. The beautifully preserved architecture and decor from the 19th century create a unique and memorable experience for visitors. The Quince Tree House is the perfect place to relax and unwind while exploring all that Cape Cod has to offer. With its convenient location, friendly staff, and comfortable accommodations, guests are sure to have a delightful stay at this one-of-a-kind institution.

Aiden By Best Western @ Cape Point is a charming lodging located at 476 Massachusetts 28 in Yarmouth, Massachusetts, United States. This cozy hotel offers comfortable accommodations and modern amenities for guests looking to relax and unwind on Cape Cod. With its convenient location near local attractions and beaches, Aiden By Best Western @ Cape Point is the perfect choice for a memorable stay in the beautiful coastal town of Yarmouth.

Old Hundred House is a charming lodging establishment located at 1211 Craigville Beach Road in Barnstable, Massachusetts. This historic inn offers a cozy and welcoming atmosphere for guests looking to experience the beauty of Cape Cod. With its quaint rooms and friendly staff, Old Hundred House provides a peaceful retreat for travelers seeking a relaxing getaway. Conveniently situated near the beach, guests can enjoy the natural beauty of the area while also being close to local attractions and activities. Whether you're looking for a romantic escape or a family vacation, Old Hundred House is the perfect choice for your stay in Barnstable.

The Ruddy Turnstone Private Lodging is a charming and cozy accommodation located at 463 Main Street in Brewster, Massachusetts, United States. This private lodging offers a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. The rooms are tastefully decorated and equipped with all the necessary amenities to ensure a comfortable stay. The location is ideal for those looking to explore the beauty of Cape Cod, with easy access to nearby beaches, shops, and restaurants. Whether you are visiting for a weekend getaway or an extended vacation, The Ruddy Turnstone Private Lodging is the perfect choice for your stay.

The Waterford Inn is a charming and elegant lodging establishment located at 386 Commercial Street in the picturesque town of Provincetown, Massachusetts, United States. Situated just steps away from the waterfront, this historic inn offers guests a cozy and comfortable stay in the heart of Cape Cod. With beautifully appointed rooms, a warm and welcoming atmosphere, and impeccable service, The Waterford Inn is the perfect destination for a relaxing getaway. Enjoy stunning views, delicious breakfast options, and easy access to local shops, restaurants, and attractions during your stay at this lovely establishment.

The Benchmark Inn is a charming lodging establishment located at 6 Dyer Street in the picturesque town of Provincetown, Massachusetts. This cozy inn offers comfortable accommodations and personalized service to ensure a memorable stay for guests. With its convenient location near the town center and local attractions, the Benchmark Inn is the perfect choice for travelers looking to experience the beauty and charm of Cape Cod. Whether you are visiting for a romantic getaway, a family vacation, or a solo retreat, the Benchmark Inn provides a warm and welcoming atmosphere for all guests to enjoy.

Bradford Carver House is a charming lodging establishment located at 70 Bradford Street in the picturesque town of Provincetown, Massachusetts, United States. This historic house offers a cozy and welcoming atmosphere for guests looking to explore the beauty of Cape Cod. With comfortable accommodations and a convenient location near local attractions, Bradford Carver House is the perfect choice for a relaxing getaway in Provincetown.

The Jared Coffin House is a historic lodging establishment located at 29 Broad Street in the charming town of Nantucket, Massachusetts. This elegant inn offers luxurious accommodations in a beautifully preserved building that dates back to the early 19th century. Guests can enjoy modern amenities while experiencing the rich history and charm of Nantucket. The Jared Coffin House is the perfect destination for those seeking a unique and memorable stay on this picturesque island.

The Chestnut House is a charming lodging establishment located at 3 Chestnut Street in the picturesque town of Nantucket, Massachusetts. This cozy inn offers a warm and inviting atmosphere, perfect for a relaxing getaway or a romantic escape. The Chestnut House features comfortable accommodations, friendly staff, and a convenient location near local attractions and amenities. Guests can enjoy a peaceful stay in one of the well-appointed rooms, each designed with comfort and style in mind. Whether you're visiting Nantucket for business or pleasure, The Chestnut House is the perfect place to call home during your stay.

76 Main is a charming lodging institution located on Main Street in the picturesque town of Nantucket, Massachusetts. This cozy retreat offers guests a comfortable and inviting atmosphere, with beautifully decorated rooms and top-notch amenities. Whether you're looking for a relaxing getaway or a romantic escape, 76 Main provides the perfect setting for a memorable stay on the island. Just steps away from shops, restaurants, and the stunning beaches of Nantucket, this institution is the ideal choice for those seeking a quintessential New England experience.

The Summer House India Street is a charming lodging institution located at 31 India Street in the picturesque town of Nantucket, Massachusetts. Situated in a historic building, this cozy retreat offers guests a peaceful and relaxing atmosphere for their summer getaway. With comfortable accommodations and a convenient location near the island's attractions, The Summer House India Street is the perfect choice for those looking to experience the beauty of Nantucket. Immerse yourself in the island's rich history and natural beauty while staying at this lovely establishment.

Ships Inn is a charming lodging establishment located at 13 Fair Street in the picturesque town of Nantucket, Massachusetts. This historic inn offers a cozy and inviting atmosphere, perfect for a relaxing getaway or a romantic weekend escape. The rooms are elegantly decorated and equipped with modern amenities to ensure a comfortable stay for guests. The inn also features a beautiful garden, where guests can unwind and enjoy the peaceful surroundings. With its convenient location near the town center and the beach, Ships Inn is the perfect choice for those looking to experience the beauty of Nantucket.

Life House, Nantucket is a charming lodging institution located at 10 Cliff Road in the picturesque island of Nantucket, Massachusetts. This cozy retreat offers guests a peaceful and relaxing getaway in a beautiful seaside setting. With comfortable accommodations, friendly staff, and a convenient location near the island's attractions, Life House is the perfect place to unwind and enjoy all that Nantucket has to offer. Whether you're looking for a romantic escape or a family vacation, Life House provides a welcoming and inviting atmosphere for all guests. Experience the charm and hospitality of Nantucket at Life House.

The Carriage House is a charming lodging establishment located at 5 Ray's Court in Nantucket, Massachusetts. This historic building offers a cozy and comfortable stay for guests looking to experience the beauty and charm of Nantucket. With its quaint architecture and prime location, the Carriage House provides a peaceful retreat for visitors to relax and unwind. Whether you're exploring the island's beaches, shops, or restaurants, the Carriage House is the perfect home base for your Nantucket getaway.

Located at 20 North Water Street in Nantucket, Massachusetts, The Chapman House is a stylish boutique bed and breakfast offering a unique blend of modern design and historic charm. Built in 1830, this property features 14 rooms with king or queen-size beds, each decorated with clean lines, crisp colors, and decorative fireplaces for a touch of sophistication. Guests can relax in the common patio area throughout the day, or retreat to their smaller-side guest room with a queen bed, fine linens, AC, and WiFi access. Some rooms also feature custom drapes, padded headboards, and private baths with stand-alone showers.

Easton House is a charming lodging institution located at 17 North Water Street in the picturesque town of Nantucket, Massachusetts. Situated in the heart of this historic island, Easton House offers guests a cozy and comfortable retreat during their stay. The welcoming atmosphere and convenient location make it the perfect choice for visitors looking to experience all that Nantucket has to offer. With its classic New England architecture and warm hospitality, Easton House is the ideal place to relax and unwind while exploring the beauty of this coastal destination.

Endless Coast, A Boutique Hotel, is a charming lodging located at 2068 State Highway in Wellfleet, Massachusetts, United States. Nestled along the endless coastline, this boutique hotel offers a serene and tranquil retreat for guests looking to escape the hustle and bustle of everyday life. With its stylish decor, personalized service, and scenic views of the coast, Endless Coast provides a unique and unforgettable experience for all who stay here. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, this hotel is the perfect destination for those looking to relax and rejuvenate by the sea.

The Captain's House is a charming lodging establishment located at 350A Commercial Street in the picturesque town of Provincetown, Massachusetts. This historic building exudes character and offers guests a cozy and comfortable stay in a beautiful coastal setting. The Captain's House is known for its warm hospitality, inviting atmosphere, and convenient location near shops, restaurants, and attractions. Whether you're looking for a romantic getaway or a relaxing retreat by the sea, The Captain's House is the perfect choice for your next vacation in Cape Cod.

Bluebird Parker Beach Lodge is a charming lodging facility located at 192 South Shore Drive in the picturesque town of Yarmouth, Massachusetts, United States. Nestled along the beautiful coastline, this lodge offers guests a peaceful and relaxing retreat with stunning views of the ocean. The lodge features comfortable and cozy accommodations, perfect for a weekend getaway or a longer stay. With its convenient location near the beach, guests can enjoy swimming, sunbathing, and beachcombing just steps away from their room. Whether you're looking for a romantic escape or a family vacation, Bluebird Parker Beach Lodge is the ideal destination for a memorable stay on Cape Cod.

Barnaby Inn is a charming lodging establishment located at 36 Massachusetts 28 in the picturesque town of Harwich, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind. With its convenient location, guests can easily explore the beautiful beaches, shops, and restaurants that Harwich has to offer. Whether you are visiting for a weekend getaway or an extended vacation, Barnaby Inn is the perfect place to call home during your stay in Massachusetts.

The Crocker Tavern House is a beautifully restored historic landmark located in Barnstable Village, Massachusetts. Originally built in 1754 as a colonial-era tavern, the house now serves as a vacation home rental. With seven bedrooms and six bathrooms, it can comfortably accommodate up to 14 guests, making it perfect for family vacations or small events. The house retains many of its period details, offering guests a genuine experience of staying in a pre-revolution landmark. Situated in the historic neighborhood of Barnstable Village, guests can enjoy quaint coffee shops, restaurants, and boutiques within walking distance. The house is also just a short walk to Barnstable Harbor and Beach, where guests can enjoy outdoor activities and scenic views. For those looking to explore further, larger beaches, island ferries, and whale watch cruises are just a short drive away.

The Rockport Lodge is a charming lodging establishment located at 55 South Street in the picturesque town of Rockport, Massachusetts, United States. Surrounded by natural beauty and just a short walk from the ocean, this cozy retreat offers comfortable accommodations and a warm, welcoming atmosphere. Guests can enjoy peaceful surroundings, friendly service, and easy access to all the attractions and activities that Rockport has to offer. Whether you're looking for a relaxing getaway or a convenient home base for exploring the area, The Rockport Lodge is the perfect choice for your next stay.

By The Sea Guests is a charming lodging institution located at 57 Chase Avenue in Dennis, Massachusetts, United States. Nestled on the beach, our guest rooms offer one or two beds, private bathrooms, TVs, and mini fridges, with most rooms boasting oceanfront or partial ocean views. With 12 guest rooms in the inn, guests can enjoy a comfortable stay with breakfast included seasonally from May through October. For those seeking more space and amenities, our Suites feature open-concept layouts with full kitchens, living rooms, private bathrooms, and private decks or balconies with side partial ocean views. We offer three one-bedroom suites and two two-bedroom suites, perfect for families or larger groups. Breakfast is not included but can be purchased during peak season.

Olde Tavern Motel & Inn is a charming accommodation located at 151 Massachusetts 6A in Orleans, Massachusetts. This historic establishment offers cozy rooms and suites, each uniquely decorated with a touch of old-world charm. Guests can enjoy modern amenities such as free Wi-Fi, flat-screen TVs, and comfortable bedding. The inn also features a quaint tavern where visitors can relax and enjoy a drink after a day of exploring the nearby Cape Cod attractions. With its convenient location and welcoming atmosphere, Olde Tavern Motel & Inn is the perfect choice for a relaxing getaway on the Cape.

The Sherman Guest Home is a charming lodging establishment located at 326 Lexington Street in the heart of Waltham, Massachusetts. This cozy guest home offers a warm and inviting atmosphere for visitors looking for a comfortable and convenient place to stay. With spacious rooms, modern amenities, and a friendly staff, guests can relax and unwind in style. The Sherman Guest Home is the perfect choice for travelers seeking a home away from home in the beautiful city of Waltham.

Sonder The Magnolia is a charming lodging located at 234 Newbury Street in the heart of Boston, Massachusetts. This elegant institution offers a unique and personalized experience for guests looking for a comfortable stay in the city. The Magnolia features beautifully decorated rooms, modern amenities, and a convenient location near popular attractions, restaurants, and shopping destinations. Whether you are visiting Boston for business or pleasure, Sonder The Magnolia provides a cozy and welcoming atmosphere for your stay.

Located at 592 Tremont Street in Boston, Massachusetts, The Upton is a unique lodging option that offers short term furnished rentals for daily, weekly, and monthly stays. Nestled in the historic South End neighborhood, this 20th century Victorian brownstone building features seven beautifully designed and furnished apartments. Each apartment at The Upton is individually restored and furnished to blend modern amenities with the original Victorian architecture of the brownstone. The layout of each rental varies in size, offering a personalized experience for guests. Run by a mother-daughter team, The Upton provides a warm and welcoming atmosphere for both short and extended stays in Boston.

Casa de Renovación is a charming lodging institution located at 1575 Tremont Street in the heart of Boston, Massachusetts. Our cozy rooms and welcoming atmosphere make it the perfect home away from home for travelers looking to explore all that the bustling city has to offer. With comfortable accommodations and convenient amenities, Casa de Renovación is the ideal place to relax and rejuvenate during your stay in the United States. Book your stay with us today and experience hospitality at its finest.

Villa Fiori is a charming lodging located at 218 Summer Street in the picturesque town of Manchester-by-the-Sea, Massachusetts. This cozy retreat offers a peaceful atmosphere surrounded by beautiful gardens and stunning views. Guests can relax in comfortable rooms, enjoy delicious meals in the on-site restaurant, and take advantage of nearby attractions such as the beach and shopping districts. Whether you are looking for a romantic getaway or a relaxing vacation, Villa Fiori provides the perfect setting for a memorable stay.

Morris House is a charming institution located in the historic town of Northampton, Massachusetts. This beautiful property offers a peaceful and serene environment for individuals seeking a place for rest and rejuvenation. The house is surrounded by lush greenery and is just a short distance from the bustling downtown area, providing guests with the perfect balance of tranquility and convenience. With comfortable accommodations and a welcoming atmosphere, Morris House is the ideal retreat for those looking to escape the hustle and bustle of everyday life.