TOP 30 Upscale cottages in Massachusetts

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Michael's Cottages in Brewster is a charming accommodation located at 618 Main Street in the picturesque town of Brewster, Massachusetts. The cottages offer a cozy and comfortable stay for guests looking to experience the beauty of Cape Cod. Each cottage is tastefully decorated and equipped with modern amenities to ensure a relaxing stay. The location is perfect for exploring the nearby beaches, shops, and restaurants. Whether you are looking for a romantic getaway or a family vacation, Michael's Cottages is the perfect choice for a memorable stay in Brewster.

The Cottage at Blue Heron Farm is a charming lodging option located at 212 Warner Hill Road in the picturesque town of Charlemont, Massachusetts, United States. Situated on a serene farm property, guests can enjoy a peaceful retreat surrounded by nature. The cozy cottage offers comfortable accommodations and a tranquil atmosphere, perfect for a relaxing getaway. Whether you're looking to unwind in the countryside or explore the nearby attractions, The Cottage at Blue Heron Farm provides a unique and inviting place to stay.

Sonnet & Sparrow is a chic and stylish home goods store located at 84 1/2 Cottage Street in Easthampton, Massachusetts. This store offers a unique shopping experience with upscale items that are hard to find elsewhere in western Massachusetts. The atmosphere is fashionable, attractive, and inviting, making it a must-visit destination for anyone looking to add a touch of elegance to their home decor. Whether you're in search of a statement piece or a thoughtful gift, Sonnet & Sparrow has something for everyone. Stop by and see for yourself why customers rave about this hidden gem of a store.

The Emerson Lofts is a luxurious residential building located at 26 Cottage Park Avenue in the heart of Cambridge, Massachusetts. This modern and stylish institution offers upscale living spaces with high-end finishes and amenities. Residents can enjoy spacious loft-style apartments with open floor plans, large windows, and contemporary design features. The building also features a fitness center, rooftop terrace, and concierge services for added convenience. With its prime location in the vibrant city of Cambridge, The Emerson Lofts offers a sophisticated urban living experience for those seeking a premium lifestyle.

Indigo Block Apartments is a luxurious residential complex situated at 67 East Cottage Street in the heart of Boston, Massachusetts. This modern and stylish apartment building offers a range of upscale amenities and features, including spacious floor plans, gourmet kitchens, high-end finishes, and stunning views of the city skyline. Residents can enjoy a variety of on-site facilities such as a fitness center, rooftop terrace, and private parking. With a prime location in one of Boston's most vibrant neighborhoods, Indigo Block Apartments provides a convenient and upscale living experience for its residents.

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.

The Verb Hotel is a stylish and retro-inspired lodging located at 1271 Boylston Street in the vibrant city of Boston, Massachusetts. This unique hotel offers a fun and funky atmosphere, with a nod to the music and pop culture of the 1960s and 70s. Guests can enjoy comfortable rooms, a lively on-site restaurant and bar, and convenient amenities such as free Wi-Fi and a fitness center. The Verb Hotel is the perfect choice for travelers looking for a one-of-a-kind experience in the heart of Boston.

Pretty Picky Properties is a real estate and travel agency located at 2421 Main Street in Brewster, Massachusetts. Specializing in Cape Cod vacation rentals, this agency offers a wide range of properties to choose from for your next getaway. With a focus on quality and attention to detail, Pretty Picky Properties ensures that each rental meets the highest standards of comfort and convenience. Whether you're looking for a beachfront escape or a cozy cottage near hiking trails, Pretty Picky Properties has the perfect vacation rental for you. Guests rave about the beautiful homes, great locations, and superb amenities offered by this agency. The attentive owner and property management team are quick to address any issues that may arise, ensuring a stress-free stay for all guests.

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.

Wheatleigh is a luxurious lodging institution located on Hawthorne Road in Lenox, Massachusetts, United States. This grand estate offers a unique and elegant experience for guests looking to immerse themselves in opulence and sophistication. With its stunning architecture, lush gardens, and impeccable service, Wheatleigh provides a truly unforgettable stay for those seeking a refined retreat in the heart of the Berkshires. Whether you are looking for a romantic getaway, a peaceful escape, or a lavish event venue, Wheatleigh promises to exceed your expectations and create lasting memories.

The Black Swan Lee - Lenox, Ascend Hotel Collection is a charming lodging institution located at 435 Laurel Street in Lee, Massachusetts, United States. This unique hotel offers a cozy and inviting atmosphere for guests to relax and unwind during their stay. With comfortable accommodations and top-notch amenities, The Black Swan Lee is the perfect choice for travelers looking for a memorable experience in the heart of the Berkshires. Whether you are visiting for business or pleasure, this hotel is sure to exceed your expectations with its exceptional service and convenient location. Book your stay at The Black Swan Lee - Lenox, Ascend Hotel Collection for a truly unforgettable experience.

Located in the charming town of Lenox, Massachusetts, Gateways Inn Restaurant is a multi-faceted institution offering a variety of services including a bar, fine dining restaurant, lodging accommodations, and a night club. Situated at 51 Walker Street, this elegant establishment provides guests with a unique and unforgettable experience. Whether you're looking to enjoy a delicious meal, relax in luxurious accommodations, or dance the night away, Gateways Inn Restaurant has something for everyone. With its prime location in the heart of Lenox, this institution is the perfect destination for locals and tourists alike.

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.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

The Whitlock is a charming lodging establishment located at 16 Church Street in the picturesque town of Lenox, Massachusetts. This historic building offers a cozy and inviting atmosphere for guests to relax and unwind during their stay. With comfortable accommodations and friendly staff, The Whitlock is the perfect destination for a peaceful getaway in the heart of the United States. Experience the beauty of Lenox and make unforgettable memories at The Whitlock.

The Dewey is a charming lodging establishment located at 7 Hubbard Street in Lenox, Massachusetts. This cozy inn offers comfortable accommodations in a picturesque setting, perfect for those looking to relax and unwind in the heart of the Berkshires. The Dewey's convenient location allows guests to easily explore the many attractions and activities in the area, including historic sites, art galleries, and outdoor adventures. With its warm hospitality and inviting atmosphere, The Dewey is the ideal destination for a peaceful getaway in the beautiful New England countryside.

Life House, Berkshires is a charming lodging located at 194 Pittsfield Road in Lenox, Massachusetts. Nestled in the picturesque Berkshires region, this institution offers a peaceful and serene retreat for guests looking to escape the hustle and bustle of everyday life. The accommodations are cozy and comfortable, providing a welcoming atmosphere for visitors to relax and unwind. With its convenient location and warm hospitality, Life House, Berkshires is the perfect destination for a memorable getaway in the heart of the Berkshires.

The Porches Inn at MASS MoCA is a charming lodging option located at 231 River Street in North Adams, Massachusetts, United States. Situated right next to the renowned Massachusetts Museum of Contemporary Art (MASS MoCA), this unique inn offers a cozy and inviting atmosphere with a touch of artistic flair. Guests can enjoy comfortable accommodations in a historic Victorian row house, complete with modern amenities and stylish decor. The inn also features a relaxing outdoor pool, a fitness center, and a complimentary breakfast for guests to start their day off right. With its convenient location and eclectic charm, The Porches Inn at MASS MoCA is the perfect choice for a memorable stay in 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.

67 Church Street is a charming lodging located in the heart of Lenox, Massachusetts. This historic institution offers comfortable accommodations and personalized service in a picturesque setting. Guests can enjoy the convenience of being just steps away from the town's shops, restaurants, and cultural attractions. Whether you are visiting Lenox for business or pleasure, 67 Church Street provides a cozy and welcoming home away from home.

Wyndhurst Golf & Club is a premier dining destination located at 55 Lee Road in Lenox, Massachusetts. This upscale restaurant offers a luxurious dining experience with a stunning view of the golf course. Indulge in a delicious menu featuring a variety of gourmet dishes prepared by talented chefs. The elegant atmosphere and impeccable service make Wyndhurst Golf & Club the perfect spot for a special occasion or a romantic dinner. Come and enjoy a memorable dining experience at this exquisite establishment in the heart of Massachusetts.

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 VERVE Boston Natick, Tapestry Collection by Hilton is a stylish and modern lodging destination located at 1360 Worcester Street in Natick, Massachusetts, United States. This hotel offers a unique and vibrant atmosphere, with contemporary design and upscale amenities. Guests can enjoy comfortable accommodations, delicious dining options, and convenient access to nearby attractions. Whether traveling for business or leisure, The VERVE Boston Natick provides a welcoming and luxurious experience for all visitors.

Located at 27 Patriot Place in Foxborough, Massachusetts, the Hilton Garden Inn Foxborough Patriot Place is a premier lodging destination for travelers seeking comfort and convenience. Situated near Gillette Stadium and Patriot Place, guests can enjoy easy access to shopping, dining, and entertainment options. The hotel offers spacious and modern rooms, a fitness center, an indoor pool, and a delicious on-site restaurant. Whether visiting for business or pleasure, guests can expect exceptional service and a memorable stay at this upscale hotel.

The Renaissance Boston Patriot Place Hotel is a luxurious lodging option located at 28 Patriot Place in the vibrant town of Foxborough, Massachusetts. Situated in the heart of the bustling Patriot Place entertainment complex, this hotel offers guests a convenient and stylish place to stay while exploring the area. With modern amenities, spacious rooms, and impeccable service, the Renaissance Boston Patriot Place Hotel is the perfect choice for travelers looking for a comfortable and upscale accommodation experience. Whether visiting for business or pleasure, guests can enjoy easy access to nearby attractions, dining options, and entertainment venues during their stay.

AC Hotel by Marriott Boston Cambridge is a stylish and modern lodging option located at 10 Acorn Park Drive in Cambridge, Massachusetts. Situated in the heart of the bustling city, this hotel offers a convenient location for both business and leisure travelers. The sleek and contemporary design of the hotel creates a sophisticated atmosphere for guests to relax and unwind. With comfortable accommodations, upscale amenities, and impeccable service, AC Hotel by Marriott Boston Cambridge is the perfect choice for a memorable stay in the historic city of Cambridge.

Freepoint Hotel Cambridge, Tapestry Collection by Hilton is a modern and stylish lodging option located at 220 Alewife Brook Parkway in Cambridge, Massachusetts, United States. This unique hotel offers a blend of sophisticated design, upscale amenities, and personalized service to ensure a comfortable stay for guests. The property features beautifully appointed rooms, a fitness center, a restaurant, and event space for meetings and special occasions. Conveniently located near Harvard University and other popular attractions, Freepoint Hotel Cambridge is the perfect choice for business and leisure travelers alike. Experience the charm and hospitality of this Hilton Tapestry Collection hotel during your next visit to Cambridge.