TOP 10 Best hotel in Stockbridge, Massachusetts

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Located in the charming town of West Stockbridge, Massachusetts, the Pleasant Valley Motel offers comfortable and affordable lodging for those looking to explore the beautiful Berkshires region. Situated at 42 West Stockbridge Road, this cozy motel provides a peaceful retreat for visitors seeking a relaxing getaway. With its convenient location and friendly staff, Pleasant Valley Motel is the perfect choice for travelers looking for a comfortable stay in West Stockbridge.

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.

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.

West Stockbridge is a charming institution located at 47 Albany Road in the picturesque town of West Stockbridge, Massachusetts. This historic institution offers a unique blend of cultural experiences, including art galleries, live music performances, and community events. Visitors can explore the quaint shops and restaurants in the area, or simply enjoy the scenic beauty of the Berkshire Mountains. West Stockbridge is a must-visit destination for anyone looking to immerse themselves in the rich history and vibrant culture of this New England town.

Stockbridge Housing Authority, located at 5 Pine Street in Stockbridge, Massachusetts, is dedicated to providing quality, affordable independent living for seniors and disabled individuals in the peaceful Berkshires region. Led by Executive Director Andrea Lindsay, the institution offers 50 one-bedroom apartments and 1 two-bedroom apartment at Heaton Court, with a waiting list in place. Veterans and Stockbridge residents receive preference on the waiting list. Applicants must be 60 years of age or older, or disabled under 60, and meet additional eligibility criteria, including passing a CORI check. Rent is based on 30% of the resident's monthly gross income, minus annualized IRS-allowable medical deductions, and includes heat, hot water, and electric. The property is 100% smoke-free.

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.

Travelodge by Wyndham Great Barrington Berkshires is a cozy and comfortable lodging option located at 400 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the picturesque Berkshires region, this hotel offers convenient access to local attractions, restaurants, and outdoor activities. The rooms are clean and well-appointed, providing guests with a relaxing retreat after a day of exploring. The friendly staff is always ready to assist with any needs or questions, ensuring a pleasant stay for all visitors. Whether you are in town for business or leisure, Travelodge by Wyndham Great Barrington Berkshires is the perfect choice for your accommodations.

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.

Welcome to Monument Mountain Motel, a budget-friendly lodging option in the heart of Great Barrington, Massachusetts. Located in the beautiful Berkshire Mountains, our motel offers comfortable rooms and family-style amenities. Whether you're in town for business or pleasure, our convenient location puts you near iconic attractions such as Tanglewood Music Festival, Ski Butternut Resort, and the Norman Rockwell Museum. At Monument Mountain Motel, we strive to provide a pleasant and affordable experience for all our guests. Enjoy free wifi, in-room microwaves and fridges, and a spacious patio with barbecue facilities. Family travelers will appreciate our family-friendly amenities, while business travelers will find our simplicity and affordability to be just what they need.

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.

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.

Briarcliff Motel is a charming lodging establishment located at 506 Stockbridge Road in Great Barrington, Massachusetts, United States. Nestled in the picturesque Berkshire Mountains, this cozy motel offers comfortable and affordable accommodations for travelers looking to explore the beauty of the region. With its convenient location and friendly staff, Briarcliff Motel is the perfect choice for a relaxing getaway in the heart of New England.

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 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.

Tanglewood Suites is a charming lodging establishment located in Stockbridge, Massachusetts, United States. Nestled in the overgrown woods, this peaceful retreat offers cozy and comfortable suites for guests seeking a tranquil escape from the hustle and bustle of city life. With its rustic charm and serene surroundings, Tanglewood Suites is the perfect destination for nature lovers and those looking to unwind and relax in a picturesque setting. Enjoy the beauty of the Berkshires while staying at Tanglewood Suites, where hospitality and comfort meet in perfect harmony.

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.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

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 Constance is a charming lodging located at 11 Old Stockbridge Road in Lenox, Massachusetts. This historic institution offers cozy accommodations in a picturesque setting, perfect for a relaxing getaway in the heart of the Berkshires. Guests can enjoy comfortable rooms, beautiful gardens, and personalized service during their stay. Whether you're looking for a weekend retreat or a longer vacation, The Constance is the perfect choice for a memorable experience in this idyllic New England town.

Henderson House is a reputable real estate and travel agency located at 39 Main Street in the charming town of Stockbridge, Massachusetts, United States. Our experienced team of professionals is dedicated to helping clients find their dream homes or plan the perfect getaway. With a focus on personalized service and attention to detail, Henderson House is your go-to destination for all your real estate and travel needs. Whether you're looking to buy or sell a property, or seeking assistance with booking a vacation, we are here to assist you every step of the way. Visit us today and experience the difference Henderson House can make in your real estate and travel endeavors.

Taggart House is a unique institution located at 18 Main Street in the charming town of Stockbridge, Massachusetts. As a health center, Taggart House offers a range of services aimed at promoting wellness and holistic healing. Whether you're looking for acupuncture, massage therapy, or nutritional counseling, their team of experienced professionals is dedicated to helping you achieve optimal health. In addition to their health services, Taggart House also operates as a real estate agency, assisting clients in finding their dream home in the picturesque Berkshires region. With a deep knowledge of the local market and a commitment to personalized service, their team can help you navigate the real estate process with ease.

White Pines Condominiums, located at 19 Hawthorne Road in Stockbridge, Massachusetts, offers a picture-perfect Carriage Barn unit with all the benefits of condo living. This home features an open common space with a wall of windows for natural light, a pretty setting, large great room, galley kitchen, separate dining area, bonus dining room/office, three bedrooms, two and a half baths, sunroom, and private deck. Residents can enjoy common amenities such as an indoor pool, exercise room, tennis courts, association beach, and walking trails. Conveniently located near Tanglewood and Lenox Village, this home is a must-see for those seeking a comfortable and luxurious living space. White Pines Condominiums serves real estate buyers and sellers in Massachusetts and New York, with a location at 47 Church Street PO Box 1650 in Lenox, Massachusetts 01240.

Stone House Properties LLC is a reputable real estate agency located at 38 Main Street in West Stockbridge, Massachusetts, United States. The agency is known for providing exceptional service to their clients, as evidenced by glowing testimonials from satisfied customers. Whether you are looking to buy or sell a property, the team at Stone House Properties LLC, led by experienced realtors Katie Soules and Jeff Astore, will guide you through the process with professionalism and expertise. Their attention to detail, excellent communication skills, and dedication to client satisfaction make them a top choice for anyone in the Berkshire County area looking to navigate the real estate market. Trust Stone House Properties LLC to help you find your dream home or successfully sell your property with ease.

Katie Soules, REALTOR - Stone House Properties LLC is a reputable real estate agency located at 38 Main Street in West Stockbridge, Massachusetts. Katie Soules is the Managing Broker, overseeing a team of 32 agents and managing the commercial division, marketing design, and training programs. With a background in International Studies and French, Katie brings a unique perspective to the real estate industry. She is actively involved in professional organizations and conferences, ensuring she stays up-to-date with industry trends. Clients praise Katie for her thoroughness, knowledge, and excellent customer service skills. She is described as a true professional who goes above and beyond to provide top-notch service. Whether it's selling a difficult property or navigating a challenging market, Katie and her team at Stone House Properties are dedicated to helping clients achieve their real estate goals.

Jacob's Tanglewood Ranch is a charming lodging institution located at 560 Stockbridge Road in Lee, Massachusetts, United States. Nestled in the picturesque countryside, this ranch offers a peaceful and tranquil retreat for guests looking to escape the hustle and bustle of city life. The rustic yet cozy accommodations provide a comfortable stay, while the surrounding Tanglewood forest offers plenty of opportunities for outdoor activities such as hiking, horseback riding, and birdwatching. Whether you're seeking a romantic getaway or a family vacation, Jacob's Tanglewood Ranch is the perfect destination for a relaxing and rejuvenating experience.

Located on Stockbridge Road in Scituate, Massachusetts, these new townhouses offer modern and comfortable lodging options for guests. Each townhouse is beautifully designed with contemporary furnishings and amenities to ensure a relaxing stay. Whether you are traveling for business or leisure, these townhouses provide a convenient and stylish accommodation choice. The location is perfect for exploring the charming town of Scituate and its nearby attractions. Experience the comfort and convenience of these new townhouses during your next visit to Massachusetts.

Welcome to Mezze Guesthouse, a serene retreat nestled above the renowned Mezze Bistro in the picturesque town of Williamstown, Massachusetts. Located at 777 Cold Spring Road, our guesthouse offers a harmonious blend of contemporary comfort and classic Mezze hospitality. Our guesthouse features five uniquely designed units, each adorned with custom finishes such as Grohe rain showers, K-Fee coffee-makers, and locally sourced treats. Choose from three elegant queen-sized units, a spacious two-bedroom suite with a queen bedroom and twin room, or indulge in our luxurious King suite complete with a separate sitting room and an oversized bathroom.