TOP 10 Charming inn for a unique experience in Stockbridge, Massachusetts

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.

Located in the charming town of West Stockbridge, Massachusetts, the Shaker Mill Inn offers a cozy and comfortable lodging experience. Situated at 2 Oak Street, this historic inn provides a peaceful retreat for guests looking to relax and unwind. The beautifully decorated rooms and friendly staff make for a memorable stay. With its convenient location and warm hospitality, the Shaker Mill Inn is the perfect choice for travelers visiting the Berkshires region.

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.

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 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.

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.

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.

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.

Welcome to The Constance, The Whitlock, & The Dewey by The Lenox Collection, your premier lodging destination nestled in the heart of Lenox, Massachusetts. Located at 11 Old Stockbridge Road, our exquisite collection of inns offers a unique blend of historical charm, modern comfort, and serene surroundings, perfect for every traveler seeking a memorable escape in the Berkshires. The Dewey: Discover our most intimate inn, featuring 12 uniquely designed guestrooms that capture the essence of historical elegance amidst peaceful natural surroundings. Situated just north of downtown Lenox, The Dewey offers a harmonious balance of accessibility to local dining and shopping, and the tranquility of Pleasant Valley. Each room, surrounded by lush treetops, invites you to relax and rejuvenate in a beautifully preserved historic setting. Ideal for the discerning traveler, The Dewey promises a serene retreat.