TOP 30 Charming lodging in Southold, New York

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The Southold Beach Motel is a charming lodging option located at 53250 North Road in Southold, New York. Situated in a picturesque coastal town, this motel offers comfortable accommodations for guests looking to relax and unwind by the beach. With easy access to the shoreline and nearby attractions, the Southold Beach Motel is the perfect destination for a peaceful getaway. Enjoy a cozy stay in this quaint motel surrounded by the beauty of the North Fork region of Long Island.

Welcome to A Walk in the Woods Bed and Breakfast, a serene retreat nestled in the heart of nature at 9680 North Bayview Road, Southold, New York. Our charming lodging offers a unique escape surrounded by the tranquility of woods, wetlands, and abundant wildlife right at our doorstep. Explore the beauty of our 11 acres of private woods, seamlessly connected to 21 acres of public forest land known as The Tall Pines of Bayview. Wander along the pristine forest trails that lead you to the breathtaking Paradise Point. Just a short stroll further, you'll find yourself at Cedar Beach, where you can soak in the stunning views of Shelter Island and The Hamptons.

The Shoals Suites & Slips is a charming lodging located at 61600 Main Road in Southold, New York. Nestled in the heart of the picturesque town, this institution offers comfortable suites and slips for visitors looking to relax and unwind by the water. With its convenient location, guests can easily explore the local attractions, shops, and restaurants nearby. Whether you're looking for a peaceful retreat or a fun-filled vacation, The Shoals Suites & Slips provides a cozy and welcoming atmosphere for all travelers.

Shorecrest Bed & Breakfast is a charming lodging located in Southold, New York. Situated at 54300 County Road 48, this cozy bed and breakfast offers a relaxing and peaceful retreat for guests looking to escape the hustle and bustle of city life. The institution features comfortable rooms, delicious breakfast options, and a warm and inviting atmosphere. With its convenient location and attentive staff, Shorecrest Bed & Breakfast is the perfect choice for a tranquil getaway in the beautiful surroundings of the North Fork of Long Island.

Welcome to North Fork Table & Inn, a charming retreat nestled in the heart of Southold, New York. Located at 57225 Main Road, our establishment effortlessly blends the warmth of a historic countryside home with the vibrant flavors of Long Island’s rich agricultural heritage. At North Fork Table, we celebrate the bounty of local farms, vineyards, and waterways, bringing you exquisite menus crafted by acclaimed restaurateur and chef, John Fraser. Our restaurant offers a delightful culinary journey, where each dish showcases the finest local ingredients, skillfully prepared to tantalize your taste buds. Whether you're indulging in a leisurely lunch, a romantic dinner, or a casual drink at our bar, you'll find a welcoming atmosphere and exceptional service.

Welcome to NYS 25/Youngs Ave Transit Station, your convenient gateway to exploring the charming town of Southold, New York. Located at the intersection of New York State Route 25 and Youngs Avenue, our transit station serves as a vital hub for residents and visitors alike, providing easy access to the beautiful North Fork of Long Island. Our station is designed to offer a seamless travel experience, whether you're commuting to work, heading out for a day of wine tasting at the local vineyards, or exploring the scenic landscapes and historic sites that Southold has to offer. With well-maintained facilities and a commitment to safety and efficiency, NYS 25/Youngs Ave Transit Station ensures a comfortable and reliable transit experience.

Welcome to Vine Sand, your serene escape nestled in the heart of Southold, New York. Located at 47100 New York 25, our charming lodging offers a perfect blend of comfort and tranquility, ideal for those looking to unwind and explore the captivating beauty of the North Fork. At Vine Sand, we pride ourselves on providing a warm and inviting atmosphere, where guests can enjoy modern amenities amidst a picturesque setting. Each of our thoughtfully designed rooms offers a cozy retreat, ensuring a restful stay. Wake up to the gentle sounds of nature and start your day with a fresh, locally-sourced breakfast that highlights the best of the region.