TOP 10 Best vacation cottages in Winthrop, Massachusetts

Winthrop Beach Inn and Suites is a charming lodging establishment located at 312 Shirley Street in the picturesque town of Winthrop, Massachusetts, United States. Situated just steps away from the beautiful Winthrop Beach, this inn offers comfortable accommodations and modern amenities for a relaxing stay by the seaside. Guests can enjoy spacious suites, complimentary breakfast, free Wi-Fi, and friendly service from the staff. Whether you are visiting for business or pleasure, Winthrop Beach Inn and Suites provides a convenient and welcoming retreat for all travelers.

Winthrop Estate is a luxurious lodging institution located at 101 Yokun Avenue in the charming town of Lenox, Massachusetts, United States. Nestled in the heart of the Berkshires, this historic estate offers guests a unique and unforgettable experience. The elegant accommodations, stunning gardens, and impeccable service make Winthrop Estate the perfect destination for a romantic getaway, family vacation, or special event. With its rich history and picturesque surroundings, Winthrop Estate truly embodies the essence of New England charm and hospitality.

Castle by the Sea is a charming lodging institution located at 100 Sargent Street in the picturesque coastal town of Winthrop, Massachusetts. This unique establishment offers guests a one-of-a-kind experience with its castle-like architecture and stunning views of the sea. Whether you are looking for a romantic getaway or a relaxing retreat, Castle by the Sea provides a tranquil and luxurious setting for your stay. Indulge in the elegant accommodations, impeccable service, and serene surroundings that make this institution a truly unforgettable destination.

The Highland Group at Compass, located at 75 Crest Avenue in Winthrop, Massachusetts, is a premier real estate agency with a 40-year history of excellence. Led by industry veteran Jim Polino, this dynamic team of highly-skilled agents is dedicated to putting their clients' needs first. They work with a diverse range of clients, from first-time buyers to experienced investors, and create personalized strategies to help each client achieve their goals. Clients praise the team for their professionalism, solid advice, and collaborative approach, making the buying or selling process smooth and efficient. The Highland Group has been recognized as a leading home seller in Winthrop for 40 consecutive years and is now backed by Compass' cutting-edge technology and support. Sales staff receive ongoing training and education to stay up-to-date with industry trends, and strong relationships with mortgage lenders ensure a high success rate with buyer financing. The Highland Group at Compass is committed to providing the highest level of service to every client, resulting in repeat business and referrals. With their elite client care and dedication to finding everyone their perfect place in the world, the Highland Group is truly shining a new light on real estate.