TOP 30 Charming guesthouse in Massachusetts

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Eagle House Motel & Guesthouse is a charming lodging option located at 8 Cleaves Street in Rockport, Massachusetts, United States. Situated in a quaint coastal town, this institution offers comfortable accommodations for travelers looking to explore the beauty of New England. With a mix of motel rooms and guesthouse suites, guests can choose the perfect setting for their stay. The Eagle House Motel & Guesthouse is known for its friendly staff, clean rooms, and convenient location near local attractions, shops, and restaurants. Whether you're visiting for a weekend getaway or an extended vacation, this cozy establishment provides a welcoming and affordable place to rest and relax.

The Brass Key Guesthouse is a charming lodging establishment located at 67 Bradford Street in the picturesque town of Provincetown, Massachusetts, United States. This cozy guesthouse offers a unique and inviting atmosphere for guests looking for a comfortable and relaxing stay. With well-appointed rooms, friendly staff, and a convenient location near local attractions, The Brass Key Guesthouse is the perfect choice for a memorable getaway on Cape Cod.

The Nauset Guesthouse is a charming lodging institution located at 1815 Nauset Road in Eastham, Massachusetts. With a focus on creating a welcoming and peaceful environment, the guesthouse offers a Deluxe King Suite with a newly remodeled bathroom and private outside entrance. Guests can enjoy the spaciousness and privacy of the suite, as well as amenities such as air-conditioning, Wi-Fi, and a Keurig coffee pot. Conveniently located near beaches, restaurants, and shopping, the guesthouse is surrounded by trees and borders the Cape Cod National Seashore, providing a tranquil setting for guests to relax and unwind. Contact the guesthouse to reserve a suite and receive a discount by April 15, 2024.

Welcome to Mezze Guesthouse, a serene retreat nestled above the renowned Mezze Bistro in the picturesque town of Williamstown, Massachusetts. Located at 777 Cold Spring Road, our guesthouse offers a harmonious blend of contemporary comfort and classic Mezze hospitality. Our guesthouse features five uniquely designed units, each adorned with custom finishes such as Grohe rain showers, K-Fee coffee-makers, and locally sourced treats. Choose from three elegant queen-sized units, a spacious two-bedroom suite with a queen bedroom and twin room, or indulge in our luxurious King suite complete with a separate sitting room and an oversized bathroom.

Sheffield Lodge is a charming lodging located at 400 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests looking to escape the hustle and bustle of city life. Whether you're seeking a romantic getaway or a relaxing vacation in nature, Sheffield Lodge provides a tranquil setting for all guests to unwind and rejuvenate. With its convenient location near local attractions and outdoor activities, this institution is the perfect destination for those seeking a peaceful retreat in the heart of Massachusetts.

Swann Lodge is a charming lodging facility located on Brett Road in the picturesque town of Monterey, Massachusetts. Surrounded by beautiful scenery and offering a peaceful retreat for guests, Swann Lodge is the perfect destination for those seeking a relaxing getaway in the United States. With cozy accommodations and a warm, welcoming atmosphere, Swann Lodge provides a comfortable and inviting stay for visitors looking to unwind and recharge in the tranquil surroundings of Monterey. Whether you're exploring the nearby attractions or simply enjoying the serenity of the area, Swann Lodge offers a memorable experience for all who stay.

Located in the picturesque town of Sandisfield, Massachusetts, Hillside Garden Inn offers a charming and relaxing Bed and Breakfast experience. Housed in the historic Elijah Twining House, dating back to 1785, guests can enjoy immaculate accommodations and gracious hospitality. The inn boasts a spacious wrap-around porch overlooking the Farmington River, as well as a screened-in patio and hilltop gazebo with stunning panoramic views of the distant hills. Sandisfield, with its beautiful landscapes and thriving arts scene, is the perfect destination for outdoor enthusiasts and culture lovers alike. The Berkshires region offers plenty of activities year-round, from skiing and hiking to water sports and cultural events. For those who enjoy shopping, Prime Outlets are just a short drive away.

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.

Washington House is a historic institution located at 16 Washington Street in Westfield, Massachusetts. This charming building serves as a hub for community events, educational programs, and cultural activities. With its rich history and welcoming atmosphere, Washington House is a beloved landmark in the heart of Westfield. Whether you're attending a lecture, concert, or art exhibit, you'll find yourself immersed in the vibrant energy of this unique institution. Come visit Washington House and experience the best of what Westfield has to offer.

Dewey House is a charming tourist attraction located at 87 South Maple Street in Westfield, Massachusetts, United States. This historic institution offers visitors a glimpse into the past with its beautifully preserved architecture and furnishings. Step back in time as you explore the rooms and learn about the fascinating history of the Dewey family who once resided here. Whether you're a history buff or simply looking for a unique and educational experience, Dewey House is a must-visit destination in Westfield.

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.

Located at 10 Richmond Mountain Road in Lenox, Massachusetts, the Apple Tree Inn is a charming lodging option that serves as the perfect retreat for those looking to nurture their creativity. Surrounded by the natural beauty of the Berkshires, this institution offers a peaceful escape from the ordinary where guests can unlock new ideas and inspiration. The inn features a picturesque 1885 Victorian main house with 13 rooms that blend historic charm with modern amenities such as Frette linens. Additionally, there is a rustic Lodge with 21 rooms that provide a cozy and tranquil setting overlooking the lush green forests and rolling hills of the Berkshires.

Located in the charming town of West Stockbridge, Massachusetts, the Shaker Mill Inn offers a cozy and comfortable lodging experience. Situated at 2 Oak Street, this historic inn provides a peaceful retreat for guests looking to relax and unwind. The beautifully decorated rooms and friendly staff make for a memorable stay. With its convenient location and warm hospitality, the Shaker Mill Inn is the perfect choice for travelers visiting the Berkshires region.

The Cottage B and B is a charming lodging establishment located at 14 Prospect Hill Road in the picturesque town of Stockbridge, Massachusetts. This historic bed and breakfast offers cozy accommodations in a beautifully restored cottage, providing guests with a peaceful and relaxing retreat. In addition to its comfortable rooms, The Cottage B and B also features a small museum showcasing local artifacts and history, adding a unique touch to the overall guest experience. Whether you are looking for a romantic getaway or a cultural escape, The Cottage B and B is the perfect destination for your next visit to Stockbridge.

33 Main offers a luxurious lodging experience curated by renowned designer Annie Selke. Located in the charming town of Lenox, Massachusetts, this upscale accommodation combines modern amenities with classic New England charm. Each room is elegantly decorated with Selke's signature style, creating a cozy and inviting atmosphere for guests to relax and unwind. With its prime location on Main Street, guests can easily explore the local shops, restaurants, and cultural attractions that Lenox has to offer. Whether you're visiting for a romantic getaway or a weekend retreat, 33 Main promises a memorable and indulgent stay in the heart of 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.

Lanesborough Country Inn is a charming lodging located at 499 South Main Street in Lanesborough, Massachusetts, United States. This cozy inn offers a peaceful retreat in the picturesque Berkshire Mountains, surrounded by beautiful nature and just a short drive from cultural attractions such as Tanglewood and the Norman Rockwell Museum. Guests can relax in comfortable rooms, enjoy delicious breakfasts, and unwind in the serene setting of the inn's grounds. Whether you're looking for a romantic getaway or a relaxing escape, Lanesborough Country Inn provides a warm and welcoming atmosphere for your stay.

Welcome to Blackinton Manor, a charming lodging establishment located at 1391 Massachusetts Avenue in North Adams, Massachusetts. This historic manor offers a unique and luxurious experience for guests looking to escape the hustle and bustle of everyday life. With its elegant architecture, beautifully landscaped grounds, and top-notch amenities, Blackinton Manor is the perfect destination for a relaxing getaway. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, our friendly staff is dedicated to ensuring your stay is comfortable and memorable. Experience the timeless elegance of Blackinton Manor during your next visit to Massachusetts.

Netherwood is a charming lodging institution located at 253 Kemp Avenue in the picturesque town of North Adams, Massachusetts, United States. Nestled in a serene and peaceful setting, Netherwood offers comfortable accommodations and a warm hospitality experience for guests seeking a relaxing getaway. With its convenient location and cozy atmosphere, Netherwood is the perfect place to unwind and enjoy the beauty of the surrounding area. Whether you are visiting for business or pleasure, Netherwood welcomes you with open arms and promises a memorable stay.

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.

Maple House Bed & Breakfast is a charming lodging establishment located at 51 Middletown Hill Road in Rowe, Massachusetts, United States. Nestled in a picturesque countryside setting, this cozy B&B offers guests a peaceful retreat surrounded by nature. The well-appointed rooms are tastefully decorated and provide a comfortable stay for visitors looking to relax and unwind. Guests can enjoy a delicious homemade breakfast each morning, made with locally sourced ingredients. The friendly staff at Maple House Bed & Breakfast are dedicated to providing exceptional hospitality and ensuring that guests have a memorable and enjoyable stay. Whether you are looking for a romantic getaway or a peaceful escape from the hustle and bustle of city life, Maple House Bed & Breakfast is the perfect destination for your next vacation.

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.

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 Farrington Inn is a cozy and welcoming lodging located at 23 Farrington Avenue in the heart of Boston, Massachusetts. Our charming inn offers comfortable accommodations and a convenient location for visitors looking to explore the city. With a friendly and attentive staff, guests can enjoy a pleasant stay in a relaxed and homely atmosphere. Whether you are traveling for business or pleasure, The Farrington Inn is the perfect choice for your next visit to Boston.

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.

Riverview Inn & Suites is a charming lodging establishment located at 1878 Wilbur Avenue in Somerset, Massachusetts, United States. Situated along the picturesque river, guests can enjoy stunning views and a peaceful atmosphere during their stay. The inn offers comfortable accommodations and modern amenities, making it the perfect choice for both leisure and business travelers. With friendly staff, convenient location, and affordable rates, Riverview Inn & Suites is the ideal destination for a relaxing getaway in Somerset.

Avalon, the Inn on Cuttyhunk, is a charming and intimate lodging establishment located on the picturesque island of Cuttyhunk in Gosnold, Massachusetts. With its stunning ocean views, cozy accommodations, and warm hospitality, Avalon provides the perfect retreat for those looking to escape the hustle and bustle of everyday life. Whether you're seeking a romantic getaway, a peaceful solo retreat, or a fun-filled family vacation, Avalon offers a relaxing and rejuvenating experience for all guests. Immerse yourself in the natural beauty of Cuttyhunk Island while staying at Avalon, where comfort, tranquility, and personalized service await you.

The Beacon Inn is a charming bed and breakfast located at 1750 Beacon Street in Brookline, Massachusetts. Housed in two beautifully restored 19th-century brownstones, our B&B offers 25 guestrooms for a cozy and comfortable stay. Whether you're visiting for business or pleasure, you'll love the combination of old-world charm and modern amenities that the Beacon Inn provides. Conveniently located near downtown Boston and the subway line, our guests have easy access to popular attractions such as Boston University, Harvard, Fenway Park, and more. If you're in town for a game, we're just minutes away from Fenway Park and the TD Garden.

The Inn on Arsenal is a charming lodging establishment located at 100 North Beacon Street in Watertown, Massachusetts. Situated in a historic building, this cozy inn offers comfortable accommodations and a welcoming atmosphere for guests looking to explore the beautiful sights and attractions of the area. With its convenient location and friendly staff, The Inn on Arsenal is the perfect choice for travelers seeking a relaxing and enjoyable stay in the United States.