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TOP 30 Luxury countryside stays in Massachusetts
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Thornewood Inn
Thornewood Inn is a charming and historic lodging located at 453 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, this cozy inn offers a tranquil escape for guests looking to relax and unwind. The beautifully appointed rooms are elegantly furnished and offer modern amenities for a comfortable stay. Guests can enjoy a delicious breakfast each morning and explore the surrounding area, which is known for its scenic beauty and cultural attractions. Whether you are seeking a romantic getaway or a peaceful retreat, Thornewood Inn is the perfect destination for your next vacation.
The Old Inn On The Green
Located in the quaint village of New Marlborough in Massachusetts, The Old Inn On The Green is a historic institution offering both bar services and lodging. The inn, originally a stagecoach relay, features beautifully restored guest rooms, fine dining in candlelit rooms, and seasonal outdoor dining on the garden terrace. The Southfield Store, open for takeout daily, is also part of the institution. Whether you are visiting for business or pleasure, for dinner or an overnight stay, The Old Inn On The Green provides a charming and authentic experience in the heart of the Berkshire region. With its picturesque surroundings of rolling fields and meadows, this historic inn is a perfect destination for those seeking a peaceful retreat in New England. Visit us at 134 Hartsville-New Marlborough Rd, New Marlborough, MA 01230 or contact us at 413-229-7924 or info@oldinn.com. Feel the love and experience the best of the oldest at The Old Inn On The Green.
Maplewood Bed & Breakfast
Maplewood Bed & Breakfast is a charming lodging establishment located at 266 Massachusetts 8 North in Otis, Massachusetts, United States. Nestled in a picturesque setting, this cozy bed and breakfast offers guests a peaceful retreat surrounded by nature. The comfortable accommodations and warm hospitality make Maplewood Bed & Breakfast the perfect choice for a relaxing getaway in the beautiful Berkshires region. With its convenient location and inviting atmosphere, guests can enjoy a memorable stay at this delightful B&B.
The Cora Needham House
The Cora Needham House is a charming lodging establishment located at 48 Main Street in Wales, Massachusetts, United States. This historic house offers a cozy and comfortable atmosphere for guests looking to relax and unwind in a picturesque New England setting. With its quaint decor and warm hospitality, The Cora Needham House provides a unique and memorable experience for those seeking a peaceful getaway in the heart of the countryside. Whether you're visiting for a weekend retreat or an extended stay, this institution is the perfect place to call home during your time in Wales.
Staffordshire Country Estates
Staffordshire Country Estates is a prestigious institution located at 500 Stafford Street in Leicester, Massachusetts, United States. Nestled in a picturesque setting, this estate offers luxurious and elegant living spaces for those seeking a refined lifestyle. With beautifully landscaped grounds, top-notch amenities, and unparalleled service, Staffordshire Country Estates provides residents with a truly exceptional living experience. Whether you're looking for a peaceful retreat or a vibrant community, this institution has something for everyone. Experience the epitome of luxury living at Staffordshire Country Estates.
Old Inn Associates
Old Inn Associates is a charming establishment located at 100 Stone Manor Dr in New Marlborough, Massachusetts. As a renowned food, lodging, and restaurant institution, we pride ourselves on providing top-notch service and comfortable accommodations for our guests. Whether you're looking for a delicious meal at our restaurant, a cozy stay in our well-appointed rooms, or a relaxing retreat in the beautiful Massachusetts countryside, Old Inn Associates has everything you need for a memorable experience. Come visit us and experience the warm hospitality and exceptional amenities that have made us a favorite destination for travelers near and far.
The Berkshires Cottage
The Berkshires Cottage is a charming real estate and travel agency located at 87 Blunt Road in Great Barrington, Massachusetts. Specializing in vacation rentals and property sales in the picturesque Berkshires region, our agency offers a wide range of cozy cottages, luxurious estates, and scenic properties for visitors and residents alike. Whether you're looking for a weekend getaway or a permanent vacation home, our experienced team is dedicated to helping you find the perfect place to call your own in this beautiful corner of the United States. Visit us at The Berkshires Cottage and let us help you make your dream of living in the Berkshires a reality.
Wind in the Pines
Wind in the Pines is a serene retreat nestled in the heart of Great Barrington, Massachusetts. Located at 949 South Main Street, this institution offers a tranquil and peaceful environment surrounded by the beauty of nature. Visitors can relax and rejuvenate in the midst of towering pine trees, listening to the gentle rustling of the wind. Whether seeking a quiet escape or a place for reflection and meditation, Wind in the Pines provides a welcoming sanctuary for all who enter its doors.
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.
Stonover Farm
Stonover Farm is a charming lodging institution located at 169 Under Mountain Road in Lenox, Massachusetts, United States. Surrounded by picturesque countryside, this tranquil farm offers a peaceful retreat for guests looking to escape the hustle and bustle of city life. The property features beautifully appointed rooms, a cozy fireplace, and stunning views of the rolling hills. Guests can enjoy a relaxing stay in this idyllic setting, with opportunities for hiking, biking, and exploring the nearby attractions. Whether you're seeking a romantic getaway or a peaceful weekend retreat, Stonover Farm provides a warm and welcoming atmosphere for a memorable stay.
The Inn at Kenmore Hall
The Inn at Kenmore Hall is a charming lodging located at 1385 State Road in Richmond, Massachusetts. Nestled in the beautiful countryside of the United States, this institution offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of everyday life. With comfortable accommodations and attentive staff, visitors can enjoy a restful stay surrounded by scenic views and serene surroundings. Whether you're looking for a romantic getaway or a quiet weekend retreat, The Inn at Kenmore Hall is the perfect destination for a memorable stay.
The Cottage B and B
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.
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.
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 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.
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.
Country Inn
Country Inn is a charming lodging establishment located at 37 Corey Road in Hancock, Massachusetts, United States. Nestled in the picturesque countryside, this quaint inn offers a cozy and inviting atmosphere for guests looking to relax and unwind. With comfortable accommodations, warm hospitality, and beautiful surroundings, Country Inn is the perfect destination for a peaceful getaway in the heart of nature. Whether you are visiting for a romantic weekend escape or a family vacation, you will feel right at home at this idyllic retreat.
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.
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.
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.
Shelburne Springs
Shelburne Springs is a charming lodging institution located at 904 Mohawk Trail in the picturesque town of Shelburne Falls, Massachusetts. Nestled in the heart of the scenic Berkshires, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests looking to unwind and relax. With its convenient location near local attractions such as the Bridge of Flowers and the Mohawk Trail State Forest, Shelburne Springs is the perfect destination for a weekend getaway or a longer stay in the beautiful New England countryside. Whether you're seeking a romantic retreat or a family vacation, Shelburne Springs provides a welcoming and memorable experience for all who visit.
Hillside House Bed & Breakfast
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.
At Poetry Ridge B&B
At Poetry Ridge B&B is a charming bed and breakfast located at 55 Stone Ridge in Greenfield, Massachusetts. Nestled in the beautiful countryside, this cozy retreat offers a peaceful and relaxing atmosphere for guests to unwind and recharge. The B&B features comfortable accommodations, delicious breakfasts, and a warm and welcoming staff. Guests can enjoy exploring the nearby hiking trails, visiting local attractions, or simply relaxing on the porch with a good book. Whether you're looking for a romantic getaway or a quiet escape from the hustle and bustle of everyday life, At Poetry Ridge B&B is the perfect destination.
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.
Big Sky Hilltop B&B
Big Sky Hilltop B&B is a charming lodging establishment located at 579 North Gulf Road in Belchertown, Massachusetts. Situated on a picturesque hilltop, this bed and breakfast offers guests stunning views of the surrounding landscape. The comfortable and cozy accommodations make for a perfect retreat for those looking to relax and unwind. The friendly staff at Big Sky Hilltop B&B are dedicated to providing guests with a memorable and enjoyable stay. Whether you are visiting for a weekend getaway or a longer vacation, this institution is the ideal choice for a peaceful and serene experience.
The Suite at Liberty Woods
The Suite at Liberty Woods is a cozy lodging option located at 111 Federal Street in Belchertown, Massachusetts. Situated in a peaceful and picturesque setting, this charming establishment offers guests a comfortable and relaxing stay. The spacious suites are tastefully decorated and equipped with modern amenities to ensure a pleasant experience. Whether you are visiting for business or leisure, The Suite at Liberty Woods provides a welcoming atmosphere and attentive service to make your stay memorable. Enjoy the tranquility of the countryside while still being conveniently located near local attractions and amenities. Book your stay today and experience the warmth and hospitality of this lovely establishment.
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- Luxury countryside stays in Amherst
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List of businesses, places and services in Massachusetts
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