TOP 30 Historical inn with breakfast in Stockbridge, Massachusetts

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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.

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.

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.

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.

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.

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.