TOP 10 Vacation homes in Stockbridge, Massachusetts

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.

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.

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.

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.

Welcome to Highwood Manor House, your quintessential retreat nestled in the heart of the Berkshires in Stockbridge, Massachusetts. Located at 01240, our historic manor offers a unique blend of timeless elegance and modern comfort, providing an idyllic setting for a relaxing getaway. Step into a world of charm and sophistication as you explore our beautifully appointed rooms, each thoughtfully designed to capture the essence of the manor's storied past while offering all the contemporary amenities you desire. Whether you're enjoying the tranquility of our lush gardens, savoring a gourmet breakfast in our sunlit dining room, or unwinding by the fireplace in our cozy lounge, Highwood Manor House promises an unforgettable experience.

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.

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.

Welcome to Barb Hassan Realty, Inc. Nestled in the heart of the beautiful Berkshires, Barb Hassan Realty, Inc. is your premier full-service real estate agency located at 31 Wendell Avenue, Pittsfield, Massachusetts. With over 35 years of dedicated service to the Northern, Central, and Southern Berkshire areas, we pride ourselves on offering professional, courteous, and responsive real estate services.

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.