Best guest house in Stockbridge, Massachusetts

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.

Michaels of Stockbridge is a vibrant establishment located at 5 Elm Street in the charming town of Stockbridge, Massachusetts. This institution offers a unique combination of a bar, restaurant, night club, and food experience all under one roof. Guests can enjoy delicious meals prepared with fresh, local ingredients, sip on expertly crafted cocktails, and dance the night away in a lively atmosphere. Whether you're looking for a casual meal with friends, a night of entertainment, or a fun night out, Michaels of Stockbridge has something for everyone. Come and experience the lively ambiance and exceptional hospitality at this popular destination in Stockbridge.

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 Williamson Guest House, your charming home away from home nestled in the heart of the picturesque town of Stockbridge, Massachusetts. Located at 32 Church Street, our guest house offers a unique blend of comfort, tranquility, and New England charm that ensures a memorable stay for all our guests. Whether you're seeking a peaceful retreat or an adventurous getaway, Williamson Guest House is the perfect destination. Our beautifully appointed rooms provide a cozy and inviting atmosphere, complete with modern amenities to cater to all your needs. Wake up to the serene sounds of nature and enjoy a delightful complimentary breakfast to start your day.

Welcome to Tappan Manor House, a charming and historic retreat nestled in the heart of Stockbridge, Massachusetts. With its timeless elegance and serene surroundings, Tappan Manor House offers an unforgettable experience for all visitors. Our beautifully restored manor is a testament to classic architecture, featuring exquisite interiors and meticulously maintained grounds. Located in the picturesque Berkshires, Tappan Manor House provides a perfect escape for those seeking tranquility and relaxation. Whether you're here for a romantic getaway, a family vacation, or a special event, our dedicated staff is committed to ensuring your stay is both comfortable and memorable. Enjoy our luxurious accommodations, savor delicious local cuisine, and explore the natural beauty and cultural attractions that Stockbridge has to offer.

Welcome to Carriage House, a charming haven nestled in the picturesque town of Stockbridge, Massachusetts. Located in the heart of the Berkshires at 01240, our establishment offers a unique blend of historic charm and modern comfort, making it the perfect destination for both locals and visitors alike. At Carriage House, we pride ourselves on providing an exceptional experience that caters to a variety of needs. Whether you're seeking a cozy retreat, a venue for special occasions, or a delightful spot to unwind, our welcoming atmosphere and attentive service ensure a memorable visit. Our beautifully appointed spaces reflect the rich history of Stockbridge while offering all the contemporary amenities you desire.

Barrington Brewery & Restaurant is a popular establishment located at 420 Stockbridge Road in Great Barrington, Massachusetts. This venue offers a unique combination of a brewery, bar, and restaurant, providing guests with a one-of-a-kind dining and drinking experience. The brewery produces a variety of craft beers that are served alongside delicious meals made from locally sourced ingredients. Whether you're looking to enjoy a casual drink with friends or indulge in a hearty meal, Barrington Brewery & Restaurant is the perfect destination for food and beer enthusiasts alike.

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.

Main Street Cafe is a charming eatery located at 40 Main Street in the picturesque town of Stockbridge, Massachusetts. This cozy restaurant offers a warm and inviting atmosphere where guests can enjoy delicious food and drinks. The menu features a variety of classic American dishes made with fresh, locally sourced ingredients. Whether you're looking for a hearty breakfast, a leisurely lunch, or a satisfying dinner, Main Street Cafe has something for everyone. Stop by and experience the friendly service and mouthwatering meals that have made this cafe a beloved dining destination in Stockbridge.

Tiffany's Cafe & Market is a charming establishment located in the heart of Stockbridge, Massachusetts. This unique cafe offers a cozy atmosphere where guests can enjoy freshly brewed coffee, delicious pastries, and a variety of homemade sandwiches and salads. In addition to their cafe offerings, Tiffany's also features a market where visitors can purchase locally sourced produce, artisanal cheeses, and gourmet pantry items. Whether you're looking for a quick bite to eat or a special ingredient for your next meal, Tiffany's Cafe & Market has something for everyone. Visit them at 4 Elm Street for a delightful culinary experience in Stockbridge.

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.