TOP 30 Luxury stays in Great Barrington, Massachusetts

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Holiday Inn Express & Suites Great Barrington - Lenox Area is a modern and comfortable lodging option located at 415 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Lenox Area, this hotel offers guests a convenient and relaxing stay with easy access to a variety of attractions and activities. The hotel features spacious and well-appointed guest rooms and suites, each equipped with modern amenities such as flat-screen TVs, free Wi-Fi, and comfortable bedding. Guests can also enjoy complimentary breakfast each morning, as well as access to a fitness center and indoor pool.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires is a cozy and modern lodging option located at 249 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the heart of the picturesque Berkshires region, this hotel offers guests a convenient and comfortable stay with close proximity to popular attractions such as Tanglewood, Norman Rockwell Museum, and Ski Butternut. The hotel features spacious and well-appointed rooms and suites, a complimentary hot breakfast buffet, a fitness center, an indoor pool, and free Wi-Fi. Whether you are visiting for business or leisure, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires provides a welcoming and relaxing atmosphere for all guests.

The Barrington Bed and Breakfast is a charming lodging establishment located at 281 Main Street in the picturesque town of Great Barrington, Massachusetts. This cozy B&B offers a warm and inviting atmosphere for guests looking for a relaxing getaway in the heart of the Berkshires. The beautifully decorated rooms are equipped with modern amenities to ensure a comfortable stay, and guests can enjoy a delicious homemade breakfast each morning. Conveniently located near shops, restaurants, and attractions, The Barrington Bed and Breakfast is the perfect choice for those seeking a peaceful retreat in a quaint New England town.

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.

Welcome to Great Barrington Resort House, your serene getaway nestled in the picturesque landscapes of Lenox, Massachusetts. Located at the heart of the Berkshires, our resort offers a perfect blend of luxury, comfort, and natural beauty. Whether you're seeking a peaceful retreat or an adventure-filled vacation, our resort is the ideal destination. At Great Barrington Resort House, we pride ourselves on providing exceptional hospitality and personalized service. Our elegantly designed rooms and suites offer breathtaking views and modern amenities to ensure a relaxing stay. Enjoy gourmet dining at our on-site restaurant, unwind at our spa, or take a dip in our heated pool.

The Wainwright Inn Bed & Breakfast is a charming and historic lodging establishment located at 518 South Main Street in the picturesque town of Great Barrington, Massachusetts, United States. This cozy inn offers comfortable accommodations in a beautiful Victorian-style setting, perfect for a relaxing getaway or romantic retreat. Guests can enjoy a delicious homemade breakfast each morning and explore the nearby attractions, including the Berkshire Mountains and quaint shops and restaurants in the town center. With its warm hospitality and inviting atmosphere, The Wainwright Inn Bed & Breakfast is the perfect choice for a memorable stay in the Berkshires.

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.

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.

Welcome to Berkshire Rental Properties, located at 29 Benton Avenue in Great Barrington, Massachusetts. Whether you're in search of a quaint cottage or a luxurious multifamily estate, Berkshire Rental Properties offers a wide range of options to suit your needs. Our listings are carefully selected for their desirability, location, and top-notch amenities, providing a step above the typical rental offerings. At Berkshire Rental Properties, we understand the allure of the Berkshires and aim to provide a seamless getaway experience for our guests. Whether you're seeking outdoor adventures, cultural experiences, or simply a relaxing retreat, our properties serve as the perfect gateway to all that the Berkshires have to offer.

The Berkshires Cottage is a charming real estate and travel agency located at 87 Blunt Road in Great Barrington, Massachusetts. Specializing in vacation rentals and property sales in the picturesque Berkshires region, our agency offers a wide range of cozy cottages, luxurious estates, and scenic properties for visitors and residents alike. Whether you're looking for a weekend getaway or a permanent vacation home, our experienced team is dedicated to helping you find the perfect place to call your own in this beautiful corner of the United States. Visit us at The Berkshires Cottage and let us help you make your dream of living in the Berkshires a reality.

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.

The Carriage House is a prestigious university located in the charming town of Great Barrington, Massachusetts, United States. Situated in a historic building, the institution offers a unique and inspiring learning environment for students. With a focus on academic excellence and innovation, the Carriage House provides a wide range of programs and resources to help students succeed in their chosen fields. The university's beautiful campus and dedicated faculty make it a top choice for those seeking a quality education in a picturesque setting.

Welcome to Alexis J. Prisendorf | Find Berkshire Properties Today With Berkshire County's Best Realtor, located at 271 Main Street, Great Barrington, Massachusetts. With over three decades of expertise in customer service and marketing, Alexis J. Prisendorf stands as a beacon of reliability and excellence in the Berkshire County real estate market. Whether you're seeking your dream home or planning to sell your property, Alexis offers unparalleled service and insight. Explore stunning properties like 26 Pine Crest Hill Road in Egremont, a luxurious 4-bedroom estate set on 4.3 acres, or the sophisticated 165 Kemble Street in Lenox, a refined 1-bedroom residence at Canyon Ranch Living. Discover the charm of North Egremont with the beautifully maintained home at 11 Hickory Hill Road, offering 3 bedrooms and 3 baths on 3.3 acres.

Welcome to Wheeler & Taylor Realty, your trusted partner in real estate since 1871. Conveniently located at 10 Elm Street in the charming town of Stockbridge, Massachusetts, we are proud to serve the vibrant communities of Southern Berkshire County. Our experienced team is dedicated to helping you find the perfect property, whether you're searching for a single-family home, a vacation retreat, or a commercial investment. At Wheeler & Taylor Realty, we specialize in a diverse range of real estate options to meet your needs. From single-family homes priced up to $750,000 to luxurious estates over $1,000,000, we cover the entire spectrum from Lenox/Richmond south to the Connecticut border. Explore beautiful homes located on or near the water, or find the perfect condo in any price range. We also offer parcels of land and commercial listings for those looking to build or invest.