TOP 30 Countryside retreats in Massachusetts

Countryside Motel is a charming lodging establishment located at 662 Spring Street in the picturesque town of Winchendon, Massachusetts. Nestled in the heart of the countryside, this cozy motel offers comfortable and affordable accommodations for travelers looking to explore the natural beauty and charm of the New England region. With clean and spacious rooms, friendly staff, and convenient amenities, Countryside Motel is the perfect home away from home for your next getaway. Experience the tranquility and serenity of the countryside at Countryside Motel.

The Countryside Motel, located at 115 Mechanic Street in Bellingham, Massachusetts, offers comfortable and affordable lodging in a charming countryside setting. Our well-maintained rooms are perfect for travelers looking for a peaceful retreat while still being conveniently located near local attractions and amenities. Whether you're visiting for business or pleasure, our friendly staff is dedicated to ensuring your stay is enjoyable and relaxing. Book your stay at Countryside Motel for a cozy and welcoming experience in the heart of beautiful Bellingham.

Coastal Countryside Properties is a premier real estate agency located at 17 South Main Street in the picturesque town of Cohasset, Massachusetts. Specializing in properties along the stunning coastal countryside, our experienced team of agents is dedicated to helping clients find their dream home or investment property. Whether you are looking for a waterfront estate, a charming cottage by the sea, or a sprawling countryside retreat, Coastal Countryside Properties has a wide range of listings to suit every taste and budget. Trust us to guide you through the buying or selling process with expertise and personalized service. Contact us today to start your journey towards finding your perfect coastal countryside property.

Hennigan Stables & Countryside is a premier equestrian facility located at 323 Oldham Street in Pembroke, Massachusetts, United States. Surrounded by picturesque countryside, our stables offer top-notch boarding services for horses of all breeds. Our experienced staff provides expert care and attention to ensure the well-being and happiness of every horse in our care. With spacious pastures, well-maintained riding arenas, and access to scenic trails, Hennigan Stables & Countryside is the perfect place for horse enthusiasts to enjoy their passion in a beautiful and peaceful setting. Come visit us and experience the beauty and tranquility of our facility firsthand.

Countryside Landscape Services is a trusted general contractor located at 677 Simonds Road in Williamstown, Massachusetts. With years of experience in the industry, we specialize in transforming outdoor spaces into stunning landscapes that enhance the beauty and value of any property. Our team of skilled professionals offers a wide range of services, including lawn care, hardscaping, irrigation, and landscape design. Whether you are looking to create a peaceful retreat in your backyard or enhance the curb appeal of your commercial property, Countryside Landscape Services is dedicated to providing high-quality workmanship and exceptional customer service. Contact us today to schedule a consultation and bring your landscaping vision to life.

Welcome to Countryside Village, your convenient transit station located in the heart of Lexington, Massachusetts. Situated at 02420, our station serves as a vital hub for locals and visitors alike, providing seamless connectivity to various destinations. At Countryside Village, we prioritize your comfort and efficiency, offering a range of amenities to enhance your travel experience. Whether you're commuting to work, exploring the charming town of Lexington, or embarking on a longer journey, our station is designed to meet your needs. With ample parking, real-time schedule updates, and friendly staff ready to assist you, Countryside Village ensures a smooth and pleasant transit experience. Join us and discover the ease of travel from one of Lexington's premier transit locations.

Welcome to Countryside Green, your serene escape nestled in the heart of Lexington, Massachusetts. Located on Lowell Street, this charming park offers a perfect blend of natural beauty and peaceful ambiance, making it an ideal destination for families, nature enthusiasts, and anyone seeking a breath of fresh air. Immerse yourself in the lush landscapes and picturesque scenery that define Countryside Green. Whether you're planning a leisurely stroll, a fun-filled picnic, or simply a relaxing day outdoors, our park provides the perfect setting. With well-maintained walking trails, open green spaces, and delightful picnic areas, there's something for everyone to enjoy.

Race Brook Lodge is a charming institution nestled in the beautiful countryside of Sheffield, Massachusetts. Located at 864 South Undermountain Road, this unique establishment offers a blend of health, lodging, and park amenities for guests to enjoy. From cozy accommodations to wellness retreats, Race Brook Lodge provides a tranquil escape from the hustle and bustle of everyday life. Explore the lush surroundings, unwind in the peaceful atmosphere, and rejuvenate your mind, body, and soul at this idyllic retreat in the heart of the Berkshires.

Sheffield Lodge is a charming lodging located at 400 South Undermountain Road in Sheffield, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy retreat offers comfortable accommodations and a peaceful atmosphere for guests looking to escape the hustle and bustle of city life. Whether you're seeking a romantic getaway or a relaxing vacation in nature, Sheffield Lodge provides a tranquil setting for all guests to unwind and rejuvenate. With its convenient location near local attractions and outdoor activities, this institution is the perfect destination for those seeking a peaceful retreat in the heart of Massachusetts.

The Inn at Freeman Elms Farm B&B is a charming and welcoming lodging establishment located in the picturesque town of New Marlborough, Massachusetts. Situated at 566 Mill River Great Barrington Road, this historic bed and breakfast offers a peaceful and relaxing retreat for guests looking to escape the hustle and bustle of city life. Surrounded by the natural beauty of the Berkshires, the Inn at Freeman Elms Farm B&B provides a cozy and comfortable atmosphere for guests to unwind and recharge. The property boasts beautifully appointed rooms, each uniquely decorated to provide a home away from home experience. Guests can enjoy a delicious homemade breakfast each morning, made with locally sourced ingredients.

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 Egremont Village Inn is a charming and historic lodging establishment located at 17 Main Street in the picturesque town of Egremont, Massachusetts, United States. This cozy inn offers a comfortable and welcoming atmosphere, perfect for a relaxing getaway in the Berkshires. Guests can enjoy beautifully appointed rooms, delicious meals at the on-site restaurant, and easy access to the area's many attractions and outdoor activities. Whether you're looking for a romantic retreat, a family vacation, or a solo adventure, The Egremont Village Inn is the perfect choice for your stay in the Berkshires.

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 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 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.

Laurel Ridge Bed and Breakfast is a charming lodging establishment located at 648 Southbridge Road in Warren, Massachusetts, United States. Nestled in a picturesque setting, this cozy B&B offers guests a peaceful and relaxing retreat. With comfortable accommodations and personalized service, Laurel Ridge Bed and Breakfast is the perfect choice for a weekend getaway or a romantic escape. Experience the beauty of the New England countryside while enjoying modern amenities and warm hospitality at this lovely inn.

Sturbridge Country Inn is a charming lodging establishment located at 530 Main Street in the historic town of Sturbridge, Massachusetts, United States. This quaint inn offers a cozy and welcoming atmosphere, perfect for a relaxing getaway or a romantic weekend retreat. Guests can enjoy comfortable accommodations, delicious breakfast options, and personalized service from the friendly staff. The inn's convenient location provides easy access to local attractions such as Old Sturbridge Village, restaurants, and shops. Whether you're looking for a peaceful escape or a convenient base for exploring the area, Sturbridge Country Inn is the ideal choice for your next stay in Sturbridge.

New England Motel Antiques Market is a charming lodging establishment located at 30 Palmer Road in Brimfield, Massachusetts. This unique institution offers guests the opportunity to stay in a cozy and comfortable motel while also exploring an impressive collection of antiques at the market. Whether you're a collector looking for rare finds or simply seeking a peaceful retreat in the picturesque New England countryside, this institution is the perfect destination for a memorable stay. Experience the beauty and charm of Brimfield while staying at New England Motel Antiques Market.

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.

The Stagecoach Tavern at Race Brook Lodge is a charming and historic institution located in Sheffield, Massachusetts. Situated at 854 South Undermountain Road, this cozy tavern offers a unique dining experience in a rustic setting. Guests can enjoy a variety of delicious food and drinks, from classic pub fare to gourmet entrees, all served in a warm and inviting atmosphere. Whether you're looking for a casual meal with friends or a romantic dinner for two, The Stagecoach Tavern is the perfect spot to relax and unwind. With its friendly staff, excellent service, and beautiful surroundings, this institution is a must-visit destination for anyone in the area.

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 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 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.

Twin Hills Country Club is a prestigious private club located at 700 Wolf Swamp Road in Longmeadow, Massachusetts. Nestled in the picturesque countryside, Twin Hills offers members a serene and luxurious retreat from the hustle and bustle of everyday life. With a championship golf course, state-of-the-art tennis courts, a sparkling swimming pool, and exquisite dining options, Twin Hills Country Club provides an unparalleled experience for those seeking relaxation and recreation. Whether you are looking to improve your golf game, unwind by the pool, or enjoy a gourmet meal with friends and family, Twin Hills Country Club is the perfect destination for those who appreciate the finer things in life.

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 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 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 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.

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.