Vacation deals in Stockbridge, Massachusetts

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.

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.

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.

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.

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.

Welcome to Barb Hassan Realty, Inc. – Your Trusted Real Estate Partner in the Berkshires Located at 69 South Main Street, Lanesborough, Massachusetts, Barb Hassan Realty, Inc. is your local, full-service real estate agency dedicated to serving the vibrant community of the Berkshires. With over 35 years of experience in the real estate industry and more than $155 million in career sales, our team is committed to providing professional, courteous, and responsive services for all your real estate needs.

Welcome to Suzanne Crerar at Stone House Properties, your premier real estate partner located at 38 Main Street, West Stockbridge, Massachusetts. Serving the beautiful regions of Berkshire County, Massachusetts, and Columbia County, New York's Upper Hudson Valley, we are a well-established brokerage firm dedicated to providing exceptional services for both buyers and sellers. Our region is renowned for its breathtaking natural beauty, with the Berkshires and Upper Hudson Valley offering picturesque landscapes of rolling hills and expansive valleys. In addition to the stunning scenery, our area is rich in cultural landmarks, including Tanglewood, MASS MoCA, and the Olana State Historic Site, making it a truly desirable location for your next home.