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TOP 30 Boutique stays in Massachusetts
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The Guest House at Field Farm
The Guest House at Field Farm is a charming lodging establishment located at 554 Sloan Road in beautiful Williamstown, Massachusetts. Nestled in the picturesque countryside, this guest house offers a peaceful and serene retreat for visitors looking to escape the hustle and bustle of city life. With comfortable accommodations, stunning views of the surrounding landscape, and warm hospitality, The Guest House at Field Farm is the perfect destination for a relaxing getaway. Whether you're looking to explore the nearby attractions or simply unwind in a tranquil setting, this institution provides a welcoming and cozy atmosphere for all guests.
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.
Conroy's Bed & Breakfast
Conroy's Bed & Breakfast is a charming lodging establishment located at 11 East Street in the picturesque town of Stockbridge, Massachusetts, United States. Nestled in a quaint and peaceful neighborhood, this cozy bed and breakfast offers comfortable accommodations and warm hospitality for guests looking to relax and unwind in a homely atmosphere. With its convenient location near local attractions, shops, and restaurants, Conroy's Bed & Breakfast is the perfect choice for travelers seeking a memorable stay in the heart of Stockbridge.
Hampton Terrace Inn
Located at 91 Walker Street in Lenox, Massachusetts, the Hampton Terrace Inn is a historic bed and breakfast that has been rated the #1 place to stay in Lenox on Tripadvisor. Originally built in 1897, this inn was once owned by some of the wealthiest families in the country and was among the first of the "Berkshire cottages" to welcome guests. Today, the inn offers romantic cottages and suites that have been updated with modern amenities while still preserving the property's rich history. Just a 5-minute walk from downtown Lenox, Hampton Terrace Inn is the perfect location for a Berkshires getaway. Guests can enjoy private baths, air conditioning, HDTVs, free Wi-Fi, complimentary cognac and liqueurs, and a full breakfast buffet included in their room rate. The inn also features a heated pool, jetted tubs, and fireplaces for guests to relax and unwind after a day of exploring the Berkshires.
Garden Gables Inn
Garden Gables Inn is a charming lodging establishment located at 135 Main Street in Lenox, Massachusetts, United States. Nestled in the heart of the picturesque town, this historic inn offers a tranquil escape for guests looking to relax and unwind. The beautifully landscaped gardens surrounding the property provide a peaceful setting for guests to enjoy. The inn features elegantly appointed rooms and suites, each uniquely decorated with a blend of modern amenities and classic charm. Guests can start their day with a delicious breakfast served in the cozy dining room or out on the sunny terrace. With its convenient location near local attractions, shops, and restaurants, Garden Gables Inn is the perfect choice for a memorable stay in Lenox.
Berkshire Inn
The Berkshire Inn is a charming lodging establishment located at 150 West Housatonic Street in the picturesque town of Pittsfield, Massachusetts. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to enjoy during their stay. Conveniently situated in the heart of the Berkshires, guests can easily explore the area's many attractions, including cultural venues, outdoor activities, and charming shops and restaurants. Whether visiting for business or pleasure, the Berkshire Inn is the perfect home away from home for travelers seeking a relaxing and enjoyable experience in the beautiful Berkshires region.
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.
Cornell Inn
The Cornell Inn is a charming lodging establishment located at 203 Main Street in Lenox, Massachusetts, United States. This historic inn offers cozy accommodations, friendly service, and a convenient location in the heart of the Berkshires. Guests can relax in comfortable rooms, enjoy a delicious breakfast, and explore the nearby shops, restaurants, and attractions. Whether you're visiting for a romantic getaway, a family vacation, or a business trip, the Cornell Inn is the perfect place to stay in Lenox.
The Central Downtown Inn & Suites
The Central Downtown Inn & Suites is a charming lodging option located at 20 West Housatonic Street in the heart of Pittsfield, Massachusetts. Our cozy inn offers comfortable accommodations and modern amenities for both leisure and business travelers. Conveniently situated in the bustling downtown area, guests can easily access local attractions, shops, and restaurants. Whether you are visiting for a weekend getaway or an extended stay, The Central Downtown Inn & Suites provides a relaxing and welcoming atmosphere for all guests.
THE 1896 House Inn and Country Lodgings
THE 1896 House Inn and Country Lodgings is a charming accommodation located at 910 Cold Spring Road in the picturesque town of Williamstown, Massachusetts. This historic institution offers a cozy and comfortable stay in a beautiful countryside setting. With a range of accommodations to choose from, including rooms in the main inn and private cottages, guests can enjoy a peaceful retreat surrounded by nature. The inn also features a delicious on-site restaurant, perfect for enjoying a meal after a day of exploring the nearby attractions such as the Williams College Museum of Art or the Clark Art Institute. Whether you are looking for a romantic getaway or a family vacation, THE 1896 House Inn and Country Lodgings provides a welcoming and relaxing atmosphere for all guests.
Chambery Inn
Chambery Inn is a charming lodging and spa located at 199 Main Street in Lee, Massachusetts. This historic inn offers a tranquil and luxurious retreat for guests seeking a peaceful getaway in the heart of the Berkshires. The beautifully appointed rooms feature elegant decor and modern amenities, creating a cozy and inviting atmosphere for relaxation. Guests can indulge in rejuvenating spa treatments, unwind in the serene garden courtyard, or explore the nearby attractions and activities in the picturesque town of Lee. With its convenient location and exceptional service, Chambery Inn is the perfect destination for a memorable and rejuvenating stay.
Morgan House Inn & Restaurant
Morgan House Inn & Restaurant is a charming establishment located at 33 Main Street in Lee, Massachusetts, United States. This institution offers a cozy and inviting atmosphere perfect for enjoying a meal or drinks with friends and family. The restaurant serves delicious food made with fresh, locally sourced ingredients, while the bar offers a variety of cocktails, wines, and beers. Whether you're looking for a casual meal or a special occasion dinner, Morgan House Inn & Restaurant is the perfect place to relax and indulge in good food and drinks.
Jonathan Foote 1778 House Bed & Breakfast
The Jonathan Foote 1778 House Bed & Breakfast is a charming and historic lodging establishment located at 1 East Street in Lee, Massachusetts. This beautiful inn offers cozy and comfortable accommodations in a quaint setting, perfect for a relaxing getaway. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions and activities in the picturesque town of Lee. With its warm hospitality and unique colonial-era charm, the Jonathan Foote 1778 House Bed & Breakfast is the perfect destination for a memorable stay in the United States.
Lanesborough Country Inn
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.
Blackinton Manor
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.
The Constance
The Constance is a charming lodging located at 11 Old Stockbridge Road in Lenox, Massachusetts. This historic institution offers cozy accommodations in a picturesque setting, perfect for a relaxing getaway in the heart of the Berkshires. Guests can enjoy comfortable rooms, beautiful gardens, and personalized service during their stay. Whether you're looking for a weekend retreat or a longer vacation, The Constance is the perfect choice for a memorable experience in this idyllic New England town.
Hotel Downstreet
Hotel Downstreet is a charming lodging establishment located at 40 Main Street in the quaint town of North Adams, Massachusetts. Situated in the heart of the United States, this hotel offers a cozy and comfortable stay for guests looking to explore the beauty of the Berkshires region. With its convenient location and warm hospitality, Hotel Downstreet is the perfect choice for travelers seeking a relaxing and enjoyable getaway.
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.
Mount Royal Inn
The Mount Royal Inn is a charming lodging located at 99 Howland Avenue in the picturesque town of Adams, Massachusetts. This cozy inn offers comfortable accommodations for travelers looking to explore the beauty of the Berkshires region. With its convenient location and welcoming atmosphere, the Mount Royal Inn is the perfect choice for a relaxing getaway or a romantic weekend retreat. Enjoy the peaceful surroundings and friendly service at this delightful institution in the heart of New England.
Netherwood
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.
Harbour House Inn B&B
Harbour House Inn B&B is a charming lodging establishment located at 725 North State Road in the picturesque town of Cheshire, Massachusetts, United States. This cozy bed and breakfast offers comfortable accommodations in a historic building, with a warm and inviting atmosphere. Guests can enjoy a delicious homemade breakfast each morning, as well as access to a peaceful garden and relaxing common areas. Whether you are looking for a romantic getaway or a peaceful retreat in the Berkshires, Harbour House Inn B&B is the perfect choice for your stay.
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.
26 Church Street
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.
1-A Lenox Bed & Breakfast
1-A Lenox Bed & Breakfast is a charming lodging located at 31 Delafield Drive in Lenox, Massachusetts. This cozy bed and breakfast offers a comfortable and welcoming atmosphere for guests looking to relax and unwind in the heart of the Berkshires. The beautifully decorated rooms feature modern amenities and luxurious touches to ensure a memorable stay. Guests can enjoy a delicious homemade breakfast each morning and take advantage of the convenient location near local attractions, shops, and restaurants. Whether you are visiting for a romantic getaway or a weekend escape, 1-A Lenox Bed & Breakfast is the perfect choice for your stay in Lenox.
The Red Door B&B
The Red Door B&B is a charming lodging establishment located at 55 Cliffwood Street in Lee, Massachusetts, United States. This cozy bed and breakfast offers a warm and inviting atmosphere for guests looking for a relaxing getaway. The Red Door B&B features comfortable accommodations, delicious breakfast options, and personalized hospitality to ensure a memorable stay. With its convenient location and welcoming ambiance, The Red Door B&B is the perfect choice for travelers seeking a peaceful retreat in the heart of New England.
Maple House Bed & Breakfast
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.
The Worthington Inn At Four Corners
The Worthington Inn at Four Corners is a charming bed and breakfast located at 27 Old North Road in Worthington, Massachusetts. Nestled on the rolling hills of Hampshire County, this quaint Inn promises unforgettable experiences during your stay. Whether you are looking for a peaceful retreat or a romantic getaway, the Worthington Inn offers cozy accommodations and warm hospitality. Come relax and rejuvenate in the serene surroundings of this historic establishment.
Inn Nature Bed & Breakfast
Inn Nature Bed & Breakfast is a charming retreat nestled in the picturesque town of Chesterfield, Massachusetts. Located at 261 South Street, this unique establishment offers a perfect blend of relaxation, wellness, and comfort. As a bed and breakfast, guests can enjoy cozy accommodations and a delicious homemade breakfast each morning. The serene surroundings provide the ideal setting for those looking to unwind and rejuvenate.
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