The Best Resort rentals in Great Barrington, Massachusetts

Welcome to William Pitt Sotheby's International Realty - Great Barrington Brokerage, your premier destination for exceptional real estate services in the heart of the Berkshires. Located at 306 Main Street, Great Barrington, Massachusetts, our office blends the prestige of a world-renowned real estate brand with the warmth and expertise of local market knowledge. Our team is committed to providing sophisticated yet personable service to our discerning clients, ensuring a seamless experience whether you're buying or selling a home. The Berkshires, a stunning year-round resort destination, is known for its picturesque landscapes, vibrant cultural scene, and a lifestyle that combines relaxation with refinement. This area attracts a diverse array of residents from around the globe, drawn by its creative energy, world-class artisans, and exceptional farm-to-table dining experiences.

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.

Butternut Ski Area and Tubing Center is a popular tourist attraction located at 380 State Road in Great Barrington, Massachusetts. This institution offers a wide range of winter activities for visitors to enjoy, including skiing, snowboarding, and tubing. The ski area features well-maintained slopes for all skill levels, while the tubing center provides a thrilling experience for all ages. With stunning views of the surrounding area and top-notch facilities, Butternut Ski Area and Tubing Center is the perfect destination for outdoor enthusiasts looking for a fun and exciting winter adventure.

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.

Crosby House is a charming and historic institution located in the picturesque town of Great Barrington, Massachusetts. This elegant bed and breakfast offers comfortable accommodations in a beautifully restored Victorian home. Guests can enjoy a peaceful and relaxing stay, surrounded by the scenic beauty of the Berkshires. The Crosby House is known for its warm hospitality, delicious breakfasts, and personalized service. Whether you are looking for a romantic getaway or a peaceful retreat, Crosby House is the perfect destination for a memorable stay in the heart of the Berkshires.

Brook Cove is a charming lodging institution located at 30 Linda Lane in the picturesque town of Great Barrington, Massachusetts. Surrounded by lush greenery and peaceful surroundings, Brook Cove offers a serene retreat for guests looking to escape the hustle and bustle of city life. The cozy accommodations and warm hospitality make it the perfect destination for a relaxing getaway. Whether you're looking to explore the beautiful Berkshires or simply unwind in nature, Brook Cove provides a tranquil and comfortable stay for all visitors.