TOP 10 Best Unique vacations in Great Barrington, Massachusetts

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.

Berkshire Rivers Fly Fishing, located in Great Barrington, Massachusetts, is the go-to institution for fly fishing guides in Western Massachusetts and the Hudson Valley. With a focus on safety, fun, and, of course, fish, Berkshire Rivers offers private fishing trips that include all necessary gear, making it a hassle-free and enjoyable experience for all. Conveniently located within a comfortable drive from New York City and Boston, Berkshire Rivers provides fishing excursions in Berkshire County, New York's Hudson Valley, Southern Vermont, and Northwest Connecticut. Whether you're seeking a unique family adventure or hoping to reel in trophy northern pike or beautiful trout, Berkshire Rivers has something for everyone. Their excursions cater to beginners and experts alike, with customized trips to meet individual needs. With a reputation for top-notch teaching and exceptional customer service, Berkshire Rivers ensures that anglers leave not only with the satisfaction of a great catch but also with the knowledge and skills to continue enjoying the sport independently for years to come.

Welcome to the Appalachian Trail at Lake Buel Rd, a stunning natural haven nestled in the heart of Great Barrington, Massachusetts. As part of the renowned Appalachian National Scenic Trail, this picturesque park offers outdoor enthusiasts a unique opportunity to explore one of the most beautiful sections of the trail. Located at Great Barrington, MA 01230, our park provides visitors with breathtaking vistas, lush forests, and serene landscapes that are perfect for hiking, bird watching, and photography. Whether you're a seasoned hiker or a casual nature lover, the Appalachian Trail at Lake Buel Rd promises an unforgettable experience.

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.

Happy Place Berkshires is a charming clothing store located at 312 Main Street in Great Barrington, Massachusetts. Step into a world of colorful and stylish fashion where you can find the perfect outfit to express your unique personality. From trendy tops to cozy sweaters, our store offers a wide selection of clothing for men and women. Whether you're looking for a casual everyday look or a special outfit for a night out, Happy Place Berkshires has something for everyone. Come visit us and experience the joy of shopping in a welcoming and cozy environment.

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.

Manor Lane is a charming institution located at 145 Hurlburt Road in Great Barrington, Massachusetts. This real estate and travel agency offers a unique rental home with French elegance in the tranquil Berkshire mountains. The private 4 bedroom, 4 bath home is the perfect vacation rental, just 5 minutes away from the town of Great Barrington. Escape to this one-of-a-kind Berkshire vacation rental for a summer getaway or holiday retreat. Immerse yourself in the beauty of the Berkshire mountains while enjoying all that Great Barrington has to offer. Experience the best of both worlds at Manor Lane, where luxury meets relaxation in the heart of Massachusetts.

Blue Hill Retreat is a premier destination located at 212 Blue Hill Road in the picturesque town of Great Barrington, Massachusetts. As a unique institution offering both real estate and travel services, Blue Hill Retreat provides a one-of-a-kind experience for those looking to escape the hustle and bustle of everyday life. Whether you are searching for your dream vacation rental or looking to purchase a tranquil getaway property, our team of experts is dedicated to helping you find the perfect retreat. With a focus on luxury and relaxation, Blue Hill Retreat is the ideal choice for those seeking a peaceful and rejuvenating experience.

The Carriage House is a prestigious university located in the charming town of Great Barrington, Massachusetts, United States. Situated in a historic building, the institution offers a unique and inspiring learning environment for students. With a focus on academic excellence and innovation, the Carriage House provides a wide range of programs and resources to help students succeed in their chosen fields. The university's beautiful campus and dedicated faculty make it a top choice for those seeking a quality education in a picturesque setting.

Welcome to Lookout Trail, your premier destination for outdoor adventure and natural beauty in Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, our park offers a serene escape from the hustle and bustle of everyday life. Whether you're an avid hiker, a nature enthusiast, or simply seeking a peaceful retreat, Lookout Trail provides an ideal setting for all. Explore our well-maintained trails that wind through lush forests and open meadows, offering breathtaking views of the surrounding landscape. Perfect for both beginners and experienced hikers, our paths promise a memorable journey through nature's splendor.

Welcome to Beartown State Forest Site 12, your gateway to the natural beauty and tranquility of Great Barrington, Massachusetts. Nestled in the heart of Beartown State Forest, our site offers a unique blend of campground, lodging, and park experiences, perfect for nature enthusiasts and adventure seekers alike. At Beartown State Forest Site 12, you can immerse yourself in the serene surroundings of lush forests, scenic trails, and sparkling water bodies. Whether you're planning a weekend getaway, a family camping trip, or a solo retreat, our site provides the ideal setting to unwind and reconnect with nature.

Welcome to Berkshire Hearth Realty Exclusive Buyer Broker, your dedicated partner in finding the perfect home in the beautiful Berkshires. Conveniently located at 50 Dresser Avenue in Great Barrington, Massachusetts, our real estate agency specializes exclusively in representing home buyers, ensuring your interests are our top priority. At Berkshire Hearth Realty, we pride ourselves on offering personalized and comprehensive services tailored to meet the unique needs of each client. Our team of experienced and knowledgeable agents is committed to guiding you through every step of the home-buying process, from initial consultation to closing. Whether you are a first-time buyer or looking to invest in a vacation property, we are here to provide expert advice and unparalleled support.