TOP 30 Upscale romantic stay in Massachusetts
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The Barrington Bed and Breakfast
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 Old Inn On The Green Restaurant
The Old Inn On The Green Restaurant is a charming dining establishment located at 134 Hartsville-New Marlborough Road in New Marlborough, Massachusetts, United States. The dining rooms are beautifully illuminated by candlelight and feature cozy fireplaces in each room. The restaurant boasts an award-winning wine list curated by General Manager Eric Goulange. The decor includes comfortable windsor chairs, mahogany tavern tables, iron chandeliers, and wall sconces that reflect the inn's early history. During the summer months, guests can enjoy dinner on the garden terrace under a white canopy with views of the dome steepled 19th-century Meeting House and the surrounding wooded country road. After dinner, patrons can relax in the taproom with a glass of port or retire to one of the historic bedrooms upstairs for an overnight stay.
The Federal
Located at 135 Cooper Street in Agawam, Massachusetts, The Federal is a popular food institution offering a unique dining experience in the Western MA area. Known for its delicious cuisine and welcoming atmosphere, The Federal is the perfect spot for a dinner with friends or a casual drink with family. Their menu changes seasonally, ensuring that there is always something new and exciting to try. Additionally, they now offer Family Style Dinner for 5, available for pickup or delivery through POSTO. Stay safe and healthy while enjoying the legendary risotto balls and other delectable dishes at The Federal.
Romabe Royal
Romabe Royal is a prestigious institution located at 19 Manor Lane in Oxford, Massachusetts, United States. Our institution prides itself on providing top-notch education and services to our students. With a focus on academic excellence and personal development, Romabe Royal offers a wide range of programs and resources to help students reach their full potential. Our dedicated faculty and staff are committed to creating a supportive and inclusive learning environment where students can thrive. Come join us at Romabe Royal and experience the royal treatment in your education journey.
The Royal
The Royal is a charming bar located at 160 Center Avenue in Middleborough, Massachusetts. With its cozy atmosphere and friendly staff, it is the perfect spot to unwind after a long day or catch up with friends over a drink. The Royal offers a wide selection of beers, wines, and cocktails, as well as delicious bar snacks to enjoy. Whether you're looking for a laid-back evening or a lively night out, The Royal is the place to be. Come and experience the royal treatment at this beloved neighborhood bar.
Chesapeake Inn of Lenox
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.
Stockbridge Country 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
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
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.
Devonfield Inn
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.
The Inn at Stockbridge
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 - An Annie Selke Luxury Lodging Experience
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
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.
Life House, Berkshires
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
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
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 Whately Inn
The Whately Inn is a charming establishment located in Whately, Massachusetts. Offering a blend of comfortable lodging, delicious dining options, and warm hospitality, The Whately Inn is the perfect destination for travelers looking for a cozy and inviting place to stay. Situated at 193 Chestnut Plain Road, this institution offers a variety of accommodations to suit every guest's needs. Whether you're looking for a relaxing weekend getaway or a convenient stopover during your travels, The Whately Inn has everything you need for a memorable stay. Enjoy a delectable meal at the on-site restaurant, featuring a menu of locally sourced ingredients and classic New England flavors. With its picturesque surroundings and welcoming atmosphere, The Whately Inn is a true gem in the heart of Massachusetts.
The Old Mill Inn
The Old Mill Inn, located at 87 School Street in Hatfield, Massachusetts, is a unique boutique New England Inn that offers a modern and upscale experience with an urban industrial feel. Recently renovated in January 2021, the Inn has completely refurbished all rooms and suites, providing guests with a one-of-a-kind stay. The Conway Room is available for patrons with mobility challenges, offering extra comforts and accommodations. Situated on the bank of the Mill River, guests can enjoy the relaxing sound of the rushing river and waterfall. The Old Mill Inn, originally built in 1870 as a grist mill, has a rich history of transformations and now serves as a boutique hotel with nine rooms and four guest suites with kitchens. Conveniently located near the Five Colleges, Deerfield Academy, and downtown Northampton, the Inn is a perfect destination for a private retreat, romantic getaway, or special event.
The Black Walnut Inn
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.
Inn on Boltwood
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
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.
Hilton Boston/Woburn
The Hilton Boston/Woburn is a luxurious lodging institution located at 2 Forbes Road in Woburn, Massachusetts, United States. This upscale hotel offers modern amenities and comfortable accommodations for both business and leisure travelers. Guests can enjoy a range of onsite facilities including a fitness center, indoor pool, and restaurant. The hotel's convenient location provides easy access to nearby attractions and businesses, making it an ideal choice for visitors to the Boston area. Whether staying for a weekend getaway or an extended business trip, guests can expect exceptional service and a memorable stay at the Hilton Boston/Woburn.
Le Méridien Boston Cambridge
Le Méridien Boston Cambridge is a luxurious lodging institution located at 20 Sidney Street in the vibrant city of Cambridge, Massachusetts, United States. This elegant hotel offers stylish accommodations, modern amenities, and impeccable service to ensure a comfortable and memorable stay for guests. With its convenient location near Harvard University, MIT, and other attractions, Le Méridien Boston Cambridge is the perfect choice for both business and leisure travelers looking for a sophisticated and upscale experience in the heart of Cambridge.
The Inn At Woburn
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
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.
Andover Inn
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.
Hotel 1868
Hotel 1868 is a charming lodging establishment located at 1868 Massachusetts Avenue in the heart of Cambridge, Massachusetts, United States. This boutique hotel offers a unique blend of modern amenities and historic charm, providing guests with a comfortable and memorable stay. The stylish rooms are elegantly furnished and equipped with all the necessary conveniences for a relaxing visit. Guests can enjoy a delicious breakfast in the cozy dining area or explore the vibrant neighborhood filled with shops, restaurants, and attractions. Whether visiting for business or pleasure, Hotel 1868 is the perfect choice for travelers seeking a welcoming and convenient accommodation experience.
Sheraton Boston Hotel
Sheraton Boston Hotel is a luxurious and modern lodging institution located at 39 Dalton Street in the heart of Boston, Massachusetts. With its prime location in the bustling Back Bay neighborhood, guests can easily access top attractions, shopping destinations, and dining options. The hotel offers elegant accommodations, state-of-the-art amenities, and impeccable service to ensure a comfortable and memorable stay for all guests. Whether visiting for business or pleasure, Sheraton Boston Hotel provides a sophisticated and welcoming atmosphere for travelers seeking a truly exceptional experience in the historic city of Boston.
Hotel Indigo Boston Garden, an IHG Hotel
Hotel Indigo Boston Garden, an IHG Hotel, is a stylish and modern lodging option located at 280 Friend Street in the heart of Boston, Massachusetts. This boutique hotel offers a unique and vibrant atmosphere, with contemporary design and upscale amenities. Guests can enjoy comfortable and well-appointed rooms, a fitness center, a restaurant and bar, and stunning views of the city skyline. Conveniently situated near the TD Garden arena and other popular attractions, Hotel Indigo Boston Garden is the perfect choice for travelers looking for a memorable stay in this historic city.
The Colonnade Hotel
The Colonnade Hotel is a luxurious lodging option located at 120 Huntington Avenue in the heart of Boston, Massachusetts. This elegant hotel offers a blend of modern amenities and classic charm, making it the perfect destination for both business and leisure travelers. With its prime location near top attractions, upscale dining options, and shopping districts, guests can easily explore all that Boston has to offer. The Colonnade Hotel features beautifully appointed rooms, a rooftop pool with stunning city views, a fitness center, and exceptional dining options. Whether you are visiting for a weekend getaway or a business trip, The Colonnade Hotel provides a sophisticated and comfortable stay in the heart of the city.
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