Top 30 Best City getaways in Southold, New York

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.

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.

Welcome to Southold Park District, a serene and picturesque destination located at the intersection of Terry Ln and Hobart Rd in Southold, New York.

Layla Sailing is a premier travel agency located at 1410 Manhanset Avenue in Greenport, New York. Specializing in sailing adventures, Layla Sailing offers a unique and unforgettable experience for those looking to explore the open waters.

Welcome to New Vine Wine Tours, your premier destination for unforgettable winery, brewery, and distillery tour experiences on the North Fork of Long Island.

Welcome to The Farmhouse Bed and Breakfast, your serene retreat in the heart of Long Island's North Fork.

Welcome to Cedar House on Sound B&B, your serene getaway nestled in the heart of North Fork's wine country.

Arbor View House Bed and Breakfast is a luxurious lodging and spa institution located at 8900 Main Road, East Marion, New York, United States.

Welcome to Suhru Wines, a delightful destination nestled in the heart of Long Island's renowned wine country.

Welcome to The Harvest Inn, your serene retreat nestled in the heart of Long Island's picturesque North Fork.

The Inn At Harbor Knoll is a charming lodging establishment located in the heart of Greenport, New York. Situated at 424 4th Street, this beautiful inn offers guests a peaceful and luxurious retreat overlooking the picturesque harbor.

Welcome to Mattituck Florist, your premier destination for exquisite floral arrangements and gifts located in the heart of Mattituck, New York.

Welcome to Goose Creek Beach, your serene escape nestled in the charming town of Southold, New York. Situated at the heart of the picturesque North Fork, Goose Creek Beach offers a perfect blend of natural beauty and tranquil ambiance.

Welcome to New Suffolk Beach, a charming and serene tourist attraction nestled in the heart of New Suffolk, New York.

Welcome to Veterans Beach, a serene oasis nestled along the picturesque Peconic Bay Boulevard in the charming town of Mattituck, New York.

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.

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.

Hotel Moraine is a charming lodging establishment located at 62005 County Road 48 in Greenport, New York. Situated in the heart of the United States, this hotel offers a peaceful and serene atmosphere for guests to relax and unwind.

Truman Beach is a beautiful waterfront park located at 19340 Main Road in East Marion, New York. This serene and picturesque park offers stunning views of the Long Island Sound and a sandy beach perfect for sunbathing and swimming.

Welcome to Long Beach Bar Lighthouse, a historic beacon of charm and relaxation located in the scenic town of Orient, New York. Nestled on the picturesque Long Island, our lighthouse offers a unique blend of history, stunning views, and warm hospitality.

Welcome to Breakwater Beach, a serene oasis nestled in the heart of Mattituck, New York. Located at 5799-5003 Luthers Road, our beautiful park offers a perfect escape for families, nature enthusiasts, and anyone looking to unwind by the water.

Welcome to Pellegrini Vineyards, a premier destination nestled in the heart of Long Island Wine Country at 23005 Main Road, Cutchogue, New York.

Welcome to Ev&Em Vineyards, a charming oasis nestled in the heart of Long Island's famed North Fork wine country.

Welcome to Rose Hill Vineyards & Inn, a charming retreat nestled in the heart of Long Island’s North Fork.

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.

Welcome to North Fork Table & Inn, a charming retreat nestled in the heart of Southold, New York.

Welcome to Sparkling Pointe Vineyards & Winery, a premier destination nestled in the heart of Southold, New York. Located at 39750 County Road 48, our winery offers a unique and enchanting experience for wine enthusiasts and tourists alike.

Welcome to Truman's Beach, a serene natural retreat located in the picturesque area of New York 11957, United States. Nestled along the stunning coastline, Truman's Beach offers visitors a tranquil escape from the hustle and bustle of everyday life.

Welcome to Greenport Station, your gateway to the scenic beauty and vibrant community of Greenport, New York. Conveniently located at the heart of Greenport, NY 11944, our station serves as a vital transit hub for both locals and visitors alike.

Welcome to Town Beach, a serene natural haven located at 53005 County Road 48 in the charming town of Southold, New York.