TOP 10 Best Historic home guesthouse in Massachusetts

The Captain's House Plymouth is a charming and historic institution located at 8 Brewster Street in Plymouth, Massachusetts. As a real estate agency, they specialize in helping clients find their dream homes in this picturesque coastal town. Additionally, as a travel agency, they offer personalized vacation planning services to help visitors make the most of their time in Plymouth. With a team of experienced professionals and a deep knowledge of the local area, The Captain's House Plymouth is your go-to destination for all things real estate and travel in Plymouth, Massachusetts.

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.

26 Church Street is a charming lodging institution located in the heart of Lenox, Massachusetts. Situated at the address 26 Church Street, this cozy establishment offers a warm and inviting atmosphere for guests looking to experience the beauty of the Berkshires. With comfortable accommodations and a convenient location near local attractions, 26 Church Street is the perfect choice for a relaxing getaway in this picturesque New England town. Whether you're exploring the nearby shops and restaurants or simply unwinding in your well-appointed room, you'll feel right at home at this lovely inn.

Located on 60 Masterson Road in the picturesque town of Whately, Massachusetts, Hillside House Bed & Breakfast offers a charming and cozy retreat for travelers looking for a peaceful and relaxing stay. This quaint lodging institution is nestled on a hillside, providing stunning views of the surrounding countryside. Guests can enjoy comfortable accommodations, delicious homemade breakfasts, and warm hospitality from the friendly staff. Whether you are visiting for a weekend getaway or a longer vacation, Hillside House Bed & Breakfast is the perfect place to unwind and recharge in the heart of New England.

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.

Copley House is a charming lodging institution located at 239 West Newton Street in the heart of Boston, Massachusetts. This cozy and welcoming accommodation offers comfortable and affordable rooms for guests looking to explore the historic city. With its convenient location near popular attractions such as Copley Square and Newbury Street, Copley House provides a perfect home base for visitors to Boston. Whether you are traveling for business or pleasure, Copley House is the ideal place to stay during your time in the bustling city of Boston.

The Captain Otis F Thatcher House is a charming lodging institution located at 32 Old Westport Road in Dartmouth, Massachusetts, United States. This historic house offers a cozy and comfortable stay for guests looking to experience the beauty of the New England countryside. With its serene surroundings and classic architecture, the Captain Otis F Thatcher House provides a peaceful retreat for travelers seeking a relaxing getaway. Enjoy a tranquil stay in this lovely bed and breakfast, where you can unwind and recharge in a home away from home atmosphere.

The Harbor Light Inn, located at 58 Washington Street in Marblehead, Massachusetts, is a romantic hotel offering quick access to the harbor, shops, galleries, historic homes, and restaurants. Our beautiful rooms showcase a variety of styles and high-quality accommodations. All room rates include a full breakfast for two and free onsite parking. Make your stay extra special by preordering a bottle of wine or fresh flowers, or arranging a relaxing massage in your room. Experience a memorable getaway at the Harbor Light Inn.

The Daniels House Inn is a charming bed and breakfast located at 1 Daniels Street in historic Salem, Massachusetts. This quaint inn offers cozy accommodations and a warm, inviting atmosphere for guests to relax and unwind. With its convenient location near popular tourist attractions, including the Salem Witch Trials Memorial and the Peabody Essex Museum, The Daniels House Inn is the perfect place to stay while exploring all that Salem has to offer. Whether you're visiting for a weekend getaway or a longer vacation, you'll feel right at home at this charming inn.

Whitfield House is a charming lodging institution located at 26 North Street in the historic town of Plymouth, Massachusetts, United States. This quaint and cozy establishment offers comfortable accommodations for guests looking to explore the rich history and beautiful scenery of Plymouth. With its convenient location near popular attractions such as Plymouth Rock and the Mayflower II, Whitfield House is the perfect home base for a memorable vacation in this picturesque New England town. Guests can enjoy a relaxing stay in well-appointed rooms and experience warm hospitality from the friendly staff. Whether you're visiting for a weekend getaway or an extended stay, Whitfield House provides a welcoming and inviting atmosphere for all travelers.

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.

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.

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.

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.

Chelter is a cozy lodging institution located at 90 Columbia Road in the vibrant city of Boston, Massachusetts. Our welcoming establishment offers comfortable and affordable accommodation for travelers looking to explore the historic sights and cultural attractions of the city. With a convenient location and attentive staff, Chelter is the perfect home away from home for your next visit to Boston.

Bed and Breakfast Associates Bay Colony is a charming lodging institution located at 453 Beacon Street in the heart of Boston, Massachusetts. Our cozy bed and breakfast offers a personalized and welcoming experience for guests looking for a home away from home. Each room is uniquely decorated and equipped with modern amenities to ensure a comfortable stay. Our convenient location allows guests to explore the historic city with ease, while also providing a peaceful retreat to relax after a day of sightseeing. Whether you are visiting for business or pleasure, Bed and Breakfast Associates Bay Colony is the perfect choice for a memorable stay in Boston.

Peak House is a historic museum and tourist attraction located at 347 Main Street in Medfield, Massachusetts, United States. This charming institution offers visitors a glimpse into the rich history and culture of the area through its well-preserved exhibits and artifacts. Guests can explore the beautifully restored rooms and learn about the fascinating stories of the people who once called Peak House home. Whether you are a history buff or simply looking for a unique and educational experience, Peak House is a must-visit destination in Medfield.

Welcome to Williamson Guest House, your charming home away from home nestled in the heart of the picturesque town of Stockbridge, Massachusetts. Located at 32 Church Street, our guest house offers a unique blend of comfort, tranquility, and New England charm that ensures a memorable stay for all our guests. Whether you're seeking a peaceful retreat or an adventurous getaway, Williamson Guest House is the perfect destination. Our beautifully appointed rooms provide a cozy and inviting atmosphere, complete with modern amenities to cater to all your needs. Wake up to the serene sounds of nature and enjoy a delightful complimentary breakfast to start your day.

Welcome to the John H. McGill House, a charming and historic establishment located at 56 Vernon Street, Medford, Massachusetts. Nestled in the heart of the community, our business is dedicated to providing a unique and memorable experience for all our visitors. Steeped in rich history and architectural beauty, the John H. McGill House offers a warm and inviting atmosphere, perfect for hosting a variety of events or simply enjoying a peaceful retreat. Our meticulously maintained property showcases the elegance and craftsmanship of a bygone era, making it a captivating setting for gatherings, celebrations, or a quiet escape from the hustle and bustle of everyday life.

Welcome to the Lord-Baylies-Bennett House, a charming historical gem nestled in the heart of Taunton, Massachusetts. Located at 66 Winthrop Street, our establishment offers a unique blend of rich history and modern comfort, making it the perfect destination for history enthusiasts and leisure seekers alike. Step into a world where the past meets the present. Our beautifully preserved house, with its classic architecture and period furnishings, provides an authentic glimpse into the region's storied past. Each room is thoughtfully designed to offer both elegance and comfort, ensuring a memorable stay for all our guests.