The 30 Best Relaxing vacation rentals in Southold, New York

Peconic Water Sports is a premier water sports institution located at 64150 Main Road in Southold, New York. As a school, store, and travel agency, we offer a wide range of services for water sports enthusiasts of all levels. Whether you're looking to learn how to paddleboard, kayak, or jet ski, our experienced instructors are here to help you make the most of your time on the water. Our store is stocked with top-of-the-line equipment and gear for all your water sports needs, and our travel agency can help you plan the ultimate water sports vacation. Come visit Peconic Water Sports and experience the thrill of the open water!

Terrace Cottage Colony is a charming and quaint institution located in Southold, New York, United States. Nestled in a peaceful and scenic setting, this colony offers cozy cottages for visitors looking for a relaxing getaway. Surrounded by lush greenery and beautiful gardens, Terrace Cottage Colony provides a serene and tranquil atmosphere for guests to unwind and rejuvenate. With its close proximity to the beach and various local attractions, this institution is the perfect destination for those seeking a peaceful and idyllic retreat. Whether you're looking for a romantic escape or a family vacation, Terrace Cottage Colony is the ideal choice for a memorable and enjoyable stay.

Welcome to Town Beach, a serene natural haven located at 53005 County Road 48 in the charming town of Southold, New York. Nestled along the picturesque shores of the North Fork, this beautiful beach offers a perfect escape for those seeking tranquility and a connection with nature. Whether you're a local resident or a visitor exploring Long Island, Town Beach provides a stunning backdrop for a day of relaxation and recreation. With its pristine sandy shores and clear, refreshing waters, Town Beach is an ideal spot for sunbathing, swimming, or simply enjoying a peaceful stroll along the coast. The beach is a favorite among families, couples, and solo adventurers alike, offering ample space to unwind and soak in the breathtaking views of the Long Island Sound.

Welcome to Peconic Bay Yacht Club, a premier destination nestled in the heart of the picturesque North Fork of Long Island. Located at 64300 Main Road, Southold, New York, our exclusive yacht club offers a serene and luxurious escape for boating enthusiasts and those seeking a tranquil waterfront experience. At Peconic Bay Yacht Club, we pride ourselves on providing top-notch amenities and services that cater to both our members and visitors. Our state-of-the-art marina is equipped to accommodate a variety of vessels, ensuring a seamless docking experience with easy access to the pristine waters of the Peconic Bay.

Welcome to Brick Cove Marina, the premier destination for boaters and families on the North Fork of Long Island. Located at 1760 Sage Boulevard, Southold, New York, our marina offers a perfect blend of relaxation and adventure, accommodating 138 boats up to 60 feet. With exclusive access to the picturesque Peconic Bay and breathtaking beachfront views of Shelter Island, Brick Cove Marina ensures an unforgettable boating experience. Our slip holders enjoy numerous amenities, including shore power, fresh water, a private grilling area, and a state-of-the-art multisport court for pickleball, basketball, or tennis. While court time is complimentary for slip holders, it is also available for reservation by the general public.

Welcome to Kenney's Beach, your serene escape located on Sound Avenue in the charming town of Southold, New York. Nestled along the picturesque shores of the Long Island Sound, Kenney's Beach offers a perfect blend of natural beauty and relaxation. Whether you're a local resident or a visitor exploring the North Fork, our beach provides a tranquil setting for a day of sunbathing, swimming, or leisurely strolls along the shoreline. At Kenney's Beach, you'll find pristine sands, gentle waves, and breathtaking sunsets that create unforgettable memories. Our convenient location makes it easy to access nearby attractions, including local vineyards, quaint shops, and delicious dining options. With ample parking and well-maintained facilities, Kenney's Beach is an ideal destination for families, couples, and solo adventurers seeking a peaceful retreat.

Welcome to Southampton Village Motel Nestled in the heart of Southampton, New York, Southampton Village Motel offers a quintessential Hamptons experience, blending timeless elegance with modern luxury. Located at 315 New York 27A, our newly renovated motel provides the perfect retreat for those seeking a serene and exclusive getaway.