TOP 30 Best Upscale bed and breakfast in Massachusetts

The Barrington Bed and Breakfast is a charming lodging establishment located at 281 Main Street in the picturesque town of Great Barrington, Massachusetts. This cozy B&B offers a warm and inviting atmosphere for guests looking for a relaxing getaway in the heart of the Berkshires. The beautifully decorated rooms are equipped with modern amenities to ensure a comfortable stay, and guests can enjoy a delicious homemade breakfast each morning. Conveniently located near shops, restaurants, and attractions, The Barrington Bed and Breakfast is the perfect choice for those seeking a peaceful retreat in a quaint New England town.

Clarendon Square Bed and Breakfast is a charming lodging establishment located at 198 West Brookline Street in the heart of Boston, Massachusetts. This historic building offers a cozy and inviting atmosphere for guests looking for a comfortable stay in the city. The bed and breakfast features beautifully decorated rooms, each equipped with modern amenities to ensure a relaxing experience. Guests can enjoy a delicious breakfast served daily in the elegant dining area. Conveniently situated near many attractions and landmarks, Clarendon Square Bed and Breakfast is the perfect choice for travelers seeking a memorable stay in Boston.

John Randall House B&B and Condos is a charming lodging institution located at 140 Bradford Street in the picturesque town of Provincetown, Massachusetts. Situated in the United States, this cozy establishment offers a unique blend of bed and breakfast accommodations as well as condominium rentals. Guests can enjoy comfortable and stylish rooms, delicious breakfast options, and a convenient location near the town's attractions and amenities. Whether you are looking for a relaxing getaway or a fun-filled vacation, John Randall House B&B and Condos provides the perfect home away from home in Provincetown.

The Chesapeake Inn of Lenox is a charming lodging establishment located at 210 West Street in the picturesque town of Lenox, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. With its convenient location near historic sites, cultural attractions, and outdoor activities, the Chesapeake Inn of Lenox is the perfect destination for a peaceful getaway or romantic retreat. Experience the beauty and hospitality of Lenox at this charming inn.

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.

Devonfield Inn is a charming lodging establishment located at 85 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy inn offers a peaceful and serene retreat for guests seeking a relaxing getaway. The beautifully appointed rooms and suites are tastefully decorated and provide all the comforts of home. Guests can enjoy a delicious homemade breakfast each morning, as well as afternoon tea and snacks. The inn also features a lovely garden area, perfect for unwinding and taking in the natural beauty of the surrounding landscape. Whether you're looking for a romantic escape or a peaceful retreat, Devonfield Inn is the perfect destination for your next vacation.

Located at 30 East Street in Stockbridge, Massachusetts, The Inn at Stockbridge is a charming Georgian-style bed and breakfast nestled on six beautifully landscaped acres in the tranquil Berkshires. Offering three distinct lodging options to cater to every traveler's preferences, guests can choose between the elegant Main House, the cozy Cottage House, or the rustic-chic Barn. Immerse yourself in the thriving arts and culture scene of the Berkshires, with world-class museums and entertainment venues just minutes away. Explore attractions like the Norman Rockwell Museum, MASS MoCA, and Tanglewood, or enjoy exclusive offerings such as tee times at Stockbridge Golf Club and deals at local ski resorts.

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.

Whistler's Inn is a charming lodging establishment located at 5 Greenwood Street in the picturesque town of Lenox, Massachusetts, United States. This cozy inn offers comfortable accommodations and personalized service to make guests feel right at home. With its convenient location near popular attractions such as Tanglewood and the Norman Rockwell Museum, Whistler's Inn is the perfect choice for travelers looking to experience the beauty and culture of the Berkshires. Whether you're visiting for a romantic getaway or a family vacation, Whistler's Inn provides a peaceful retreat in the heart of Lenox.

The Black Walnut Inn is a charming lodging establishment located at 1184 North Pleasant Street in Amherst, Massachusetts. Nestled in the heart of the historic town, this inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. The inn's cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a delicious breakfast in the quaint dining area or relax in the beautiful garden courtyard. With its convenient location and welcoming atmosphere, The Black Walnut Inn is the perfect choice for travelers seeking a memorable stay in Amherst.

The Inn on Boltwood is a charming and elegant institution located in the heart of Amherst, Massachusetts. Situated at 30 Boltwood Avenue, this historic property offers luxurious accommodations, exquisite dining options, and top-notch service. Whether you are looking for a comfortable place to stay, a delicious meal, or a relaxing getaway, the Inn on Boltwood is the perfect choice. With its convenient location and upscale amenities, this institution is sure to exceed your expectations and provide you with a memorable experience.

The Residence Inn by Marriott Boston Natick is a comfortable and convenient lodging option located at 1 Superior Drive in Natick, Massachusetts. This extended stay hotel offers spacious suites with fully equipped kitchens, separate living and sleeping areas, and modern amenities. Guests can enjoy complimentary breakfast, free Wi-Fi, a fitness center, and an indoor pool. The hotel is conveniently located near shopping, dining, and entertainment options, making it an ideal choice for both business and leisure travelers visiting the Boston area.

The Inn at Woburn is a charming lodging establishment located at 14 Hill Street in the picturesque town of Woburn, Massachusetts. This historic inn offers a cozy and inviting atmosphere for guests looking for a comfortable stay in a beautiful New England setting. The Inn features well-appointed rooms with modern amenities, a delicious breakfast served daily, and friendly staff who are dedicated to ensuring a memorable experience for every visitor. Whether you are in town for business or pleasure, The Inn at Woburn is the perfect choice for your next stay in Massachusetts.

The Groton Inn is a historic and charming lodging establishment located at 128 Main Street in Groton, Massachusetts, United States. Nestled in the heart of a picturesque New England town, this iconic inn offers guests a warm and inviting atmosphere with modern amenities. With its convenient location, guests can easily explore local attractions, shops, and restaurants. Whether you are visiting for business or pleasure, The Groton Inn provides a cozy and comfortable retreat for a memorable stay.

The Andover Inn is a charming and historic lodging located at 4 Chapel Avenue in Andover, Massachusetts. Situated in the heart of the town, this elegant inn offers a comfortable and inviting atmosphere for guests to relax and unwind. With beautifully appointed rooms, modern amenities, and exceptional service, the Andover Inn is the perfect choice for both business and leisure travelers. Whether you are visiting for a weekend getaway, a special event, or a business trip, the Andover Inn provides a welcoming and memorable experience for all who stay.

The Colonel Blackinton Inn, located at 203 North Main Street in Attleboro, Massachusetts, offers a cozy and historic colonial charm for guests looking for a unique dining experience. With multiple dining rooms serving delicious food, attentive staff, and a beautifully decorated ambiance, the inn is a popular choice for special occasions and casual dining alike. Join us on Wednesday, April 17th from 6:30-9pm for a fun event where you can paint a reusable cup with a bamboo lid and straw while enjoying desserts and coffee for $45 per person plus tax. Call 508-222-6022 to sign up!

Five Bridge Inn is a charming lodging establishment situated at 152 Pine Street in Rehoboth, Massachusetts. This picturesque inn offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by lush greenery and five scenic bridges, the inn provides a tranquil atmosphere for a memorable stay. The cozy rooms are tastefully decorated and equipped with modern amenities to ensure a comfortable experience. Guests can enjoy a delicious breakfast in the morning and unwind in the beautiful outdoor spaces. Whether you are looking for a romantic getaway or a peaceful weekend retreat, Five Bridge Inn is the perfect destination for a memorable stay in Massachusetts.

Essex Street Inn & Suites, part of the Ascend Hotel Collection, is a charming and cozy lodging option located in the heart of historic Newburyport, Massachusetts. Situated at 7 Essex Street, this boutique hotel offers comfortable accommodations, modern amenities, and personalized service to ensure a memorable stay for guests. Whether you are visiting for business or leisure, Essex Street Inn & Suites provides a convenient and welcoming home away from home in this picturesque coastal town.

The Garrison Inn Boutique Hotel is a charming and elegant lodging located in the heart of historic Newburyport, Massachusetts. Situated at 11 Brown Square, this boutique hotel offers luxurious accommodations in a beautifully restored 19th-century building. Guests can enjoy a unique and personalized experience with impeccable service, modern amenities, and stylish décor. The Garrison Inn is the perfect destination for travelers seeking a tranquil and sophisticated retreat in the quaint coastal town of Newburyport.

Located in the charming town of Newburyport, Massachusetts, the Compass Rose Inn offers a cozy and welcoming lodging experience. Situated at 5 1/2 Center Street, this quaint inn is the perfect destination for travelers seeking a peaceful retreat. The Compass Rose Inn boasts comfortable accommodations, friendly staff, and a convenient location near local attractions and dining options. Whether you're visiting for business or pleasure, you'll feel right at home at the Compass Rose Inn.

Located at 101 Main Street in Rowley, Massachusetts, Briar Barn Inn is a charming lodging institution just 30 miles from the bustling city of Boston. Offering a blend of laid-back luxury and heartfelt hospitality, Briar Barn Inn provides a quintessential country inn experience with a modern twist. The farmhouse setting of the inn features 30 guest rooms that combine rustic charm with contemporary finishes, creating a serene retreat or romantic getaway. The Spa at Briar Barn Inn offers a tranquil escape with three treatment rooms for massages, facials, wax treatments, and more. The intimate spa provides a relaxing environment for guests to indulge in personalized wellness treatments.

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.

Prentiss House by Thatch is a charming lodging institution located at 6 Prentiss Street in the heart of Cambridge, Massachusetts, United States. This historic building offers a unique blend of modern amenities and old-world charm, providing a cozy and comfortable stay for guests. The elegant decor and personalized service create a welcoming atmosphere for visitors looking to explore the vibrant city of Cambridge. With its convenient location and warm hospitality, Prentiss House by Thatch is the perfect choice for travelers seeking a memorable stay in this bustling New England city.

The Fidelia Bridges Guest House at Hawthorne Hotel is a charming lodging establishment located at 98 Essex Street in historic Salem, Massachusetts. Named after the renowned American artist Fidelia Bridges, this guest house offers cozy and comfortable accommodations for travelers looking to experience the rich history and culture of Salem. The Hawthorne Hotel's central location makes it easy for guests to explore the city's attractions, including the Salem Witch Museum, Peabody Essex Museum, and the House of the Seven Gables. With its warm hospitality and convenient amenities, the Fidelia Bridges Guest House is the perfect choice for a memorable stay in Salem.

The Hotel Marblehead is a charming and historic lodging establishment located at 264 Pleasant Street in the picturesque town of Marblehead, Massachusetts. With its elegant architecture and welcoming atmosphere, this boutique hotel offers guests a unique and memorable experience. The rooms are tastefully decorated and equipped with modern amenities, ensuring a comfortable stay for all visitors. Whether you are in town for business or pleasure, The Hotel Marblehead is the perfect place to relax and unwind. Conveniently located near local attractions and restaurants, this hotel is the ideal choice for travelers looking to explore the beauty of New England.

The Newbury Street Inn is a charming lodging establishment located at 170 Newbury Street in Peabody, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. Conveniently situated in a bustling area, guests can easily explore the nearby attractions and enjoy the local amenities. Whether visiting for business or pleasure, the Newbury Street Inn provides a home away from home for travelers seeking a comfortable and convenient place to stay in the heart of Massachusetts.

The Coach House is a charming lodging establishment located at 284 Lafayette Street in the historic city of Salem, Massachusetts. This cozy retreat offers comfortable accommodations in a quaint and picturesque setting. Guests can relax in well-appointed rooms and enjoy the warm hospitality of the staff. The Coach House is the perfect place to stay for those looking to experience the rich history and culture of Salem while enjoying a peaceful and relaxing getaway.

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.

The Captain's Manor Inn is a charming and elegant lodging located at 27 West Main Street in Falmouth, Massachusetts. This historic inn offers guests a luxurious and comfortable stay in the heart of Cape Cod. The beautifully decorated rooms, delicious breakfasts, and warm hospitality make it the perfect retreat for travelers looking for a peaceful and relaxing getaway. Whether you're exploring the nearby beaches, shops, and restaurants, or simply unwinding in the inn's beautiful gardens, The Captain's Manor Inn offers a truly unforgettable experience.

The Inn at Castle Hill is a charming lodging located at 280 Argilla Road in Ipswich, Massachusetts. Nestled in a picturesque setting, this historic inn offers guests a peaceful and relaxing retreat. With comfortable rooms, stunning views, and welcoming hospitality, The Inn at Castle Hill is the perfect destination for a weekend getaway or a romantic escape. Guests can explore the beautiful grounds, enjoy delicious meals at the on-site restaurant, and take in the natural beauty of the surrounding area. Whether you're looking for a peaceful retreat or a romantic getaway, The Inn at Castle Hill is the perfect choice for your next vacation.