TOP 30 Housing with parking in Stockbridge, Massachusetts

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Lantern House Motel is a charming lodging establishment located at 256 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts, United States. Offering comfortable and affordable accommodations, this quaint motel is the perfect choice for travelers looking to explore the beautiful Berkshires region. With its convenient location and friendly staff, Lantern House Motel provides a cozy home away from home for guests looking to relax and unwind during their stay. Whether you are visiting for business or pleasure, you are sure to enjoy your time at this welcoming institution.

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.

Welcome to Ashley House, a captivating museum and tourist attraction located at 117 Cooper Hill Road, Sheffield, Massachusetts. Nestled in the picturesque Berkshires, this historic site offers a profound journey through time, exploring the narratives of two influential figures who fought for freedom and liberty, forever altering the course of our region’s history. The Colonel John Ashley House, a cornerstone of the Upper Housatonic Valley African American Heritage Trail, stands as one of the earliest European-style dwellings in the Berkshires. Built in 1735, this remarkable Colonial-era house was once the epicenter of white political and social life in colonial Sheffield. Colonel John Ashley, a prominent and wealthy figure, owned vast lands and businesses, prospering significantly from the institution of slavery.

Welcome to the Mission House, a National Historic Landmark nestled in the heart of Stockbridge, Massachusetts. Located at 19 Main Street, our museum and garden offer an immersive journey through time, unraveling the rich tapestry of the Stockbridge Mohicans and the legacy of missionary John Sergeant. Built around 1742 by John Sergeant, the Mission House has stood as a silent witness to the evolution of Stockbridge for nearly two centuries. Originally constructed to aid Sergeant in his mission to assimilate the Mohican people, this Colonial-era house was later preserved by Mabel Choate, who relocated it to its current location. Choate enriched the property with her collection of colonial American furnishings and established a museum featuring Mohican artifacts.

Welcome to Tyringham Cobble Park, a captivating natural retreat nestled at 20 Jerusalem Road, Tyringham, Massachusetts. As a renowned park and tourist attraction, Tyringham Cobble offers an unforgettable experience for nature enthusiasts and history buffs alike. Explore the wonders of this geologic marvel, shaped by ancient tectonic movements that left exposed bedrock atop a high ridge, offering breathtaking panoramic views of the serene Tyringham Valley. The park's rich history dates back to the late 18th century when it was part of a 2,000-acre farm owned by a Shaker community. Today, it stands as a testament to conservation efforts, protected by The Trustees since 1963.

Monument Mountain Reservation/Flag Rock Trailhead Location: Great Barrington, Massachusetts 01230, United States Type: Park

Welcome to Naumkeag, a stunning museum, park, and tourist attraction nestled in the heart of Stockbridge, Massachusetts. Located at 5 Prospect Hill Road, this exquisite 48-acre estate offers a glimpse into the grandeur of the Gilded Age, featuring breathtaking gardens and a rare Berkshire "cottage" that was once the summer retreat of the Choate family. Designed in 1884 by the renowned architectural firm McKim, Mead & White, Naumkeag is a remarkable example of shingle-style architecture with 44 rooms that served as a family home for several generations. Visitors can explore the meticulously maintained landscapes, including 8 acres of formal gardens, meadows, and farmland, which provide a serene escape and a chance to step back in time. Please note that due to the estate's age and terrain, it is not wheelchair- or stroller-accessible.

Welcome to The Trustees of Reservations, a haven for nature lovers and history enthusiasts alike, located at 1 Sergeant Street, Stockbridge, Massachusetts. As a distinguished museum and tourist attraction, we are dedicated to preserving the exceptional scenic, historic, and ecological treasures of Massachusetts. Our mission is to protect the places you love for their trails, history, gardens, and beaches, recognizing that nature and culture enrich our lives and soothe the soul. Explore the beauty of Massachusetts through our diverse offerings, from historic estates to breathtaking natural landscapes. Immerse yourself in our scenic trails, picturesque gardens, and serene beaches that promise a rejuvenating experience. For those interested in history, delve into the rich past of the region with guided tours and educational programs.

Mountain Meadow Preserve: Your Gateway to Nature's Splendor Welcome to Mountain Meadow Preserve, a captivating natural haven straddling the Massachusetts-Vermont border. Located at Mason Street, Williamstown, Massachusetts, this enchanting park and tourist attraction offers a delightful blend of forest, field, wetland, and wildflower meadow, perfect for both novice hikers and seasoned naturalists.

Welcome to Titus Mansion Ruins, a captivating destination nestled in the heart of the Tyringham Valley at 264 Main Road, Tyringham, Massachusetts. This enchanting locale invites you to explore the harmonious blend of history, art, and nature that defines Ashintully Gardens. Originally established in the early 20th century by Robb and Grace de Peyster Tytus, the estate once featured the magnificent Marble Palace, a Georgian-style mansion renowned for its reflective stucco exterior. Today, visitors can wander through the evocative ruins of the Marble Palace, where the enduring Doric columns stand as solemn sentinels of its storied past. The gardens, sculpted over three decades by contemporary classical composer John McLennan, offer a serene escape with their intricate mix of formal and informal designs. McLennan's dedication to creating this verdant masterpiece was recognized with the prestigious Hunnewell Medal from the Massachusetts Horticultural Society in 1997.

Welcome to Fork Factory Brook Reservation, a hidden gem nestled in the heart of Medfield, Massachusetts. Located on Hartford Street, this picturesque park and tourist attraction offers a serene escape into nature's embrace. Managed by The Trustees of Reservations, Fork Factory Brook Reservation is dedicated to preserving the scenic, historic, and ecological treasures of Massachusetts for all to enjoy. Explore the park's winding trails, which meander through lush woodlands and alongside the tranquil brook that gives the reservation its name. With almost 10 miles of family-friendly paths, visitors can immerse themselves in the beauty of diverse landscapes, from dense forests to open fields and charming wetlands. This idyllic setting is perfect for walking, hiking, and nature watching, offering a peaceful retreat from the hustle and bustle of everyday life.