Top 30 Best Relaxing accommodations 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 New Vine Wine Tours, your premier destination for unforgettable winery, brewery, and distillery tour experiences on the North Fork of Long Island.

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

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.

Welcome to Peconic Bay Yacht Club, a premier destination nestled in the heart of the picturesque North Fork of Long Island.

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 Brick Cove Marina, the premier destination for boaters and families on the North Fork of Long Island.

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

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

Welcome to Safe Harbor Stirling, your premier storage destination located at 1410 Manhanset Avenue, Greenport, New York.

Welcome to Sannino Vineyard, your idyllic retreat nestled in the heart of Long Island Wine Country at 15975 County Road 48, Cutchogue, New York.

Welcome to Silver Sands Motel & Beach Bungalows, a charming lodging establishment located at 1400 Silvermere Road in Greenport, New York.

American Beech is a charming institution located at 300 Main Street in the picturesque town of Greenport, New York. This versatile establishment offers a range of services including a bar, restaurant, and lodging accommodations.

The Cliffside Resort Condominiums, located at 61475 North Road in Greenport, New York, offers luxurious and comfortable lodging in a stunning waterfront setting.

The Harbor Front Inn is a charming waterfront lodging located at 209 Front Street in the picturesque village of Greenport, New York.

The Blue Inn at North Fork is a charming lodging institution located at 7850 Main Road in East Marion, New York, United States. Situated near North Fork's Greenport, The Blue Inn offers picturesque accommodations with pet-friendly rooms.

The Lin Beach House is a charming seaside retreat located at 455 New York 25 in Greenport, New York. This cozy institution offers a unique blend of delicious food and comfortable lodging, making it the perfect destination for a relaxing getaway.

Welcome to The Broken Down Valise, a cozy and inviting bar nestled in the heart of Mattituck, New York.

Welcome to the Village of Greenport McCann, your perfect getaway nestled in the heart of Greenport, New York.

Welcome to Claudio's Waterfront, a vibrant bar and restaurant located at 111 Main Street, Greenport, New York. Nestled in the heart of the picturesque North Fork, Claudio's Waterfront offers a unique dining experience with stunning views of the harbor.

Welcome to Claudio's Tavern & Grill, your premier destination for delicious food and great times in the heart of Greenport, New York.

Townsend Manor Inn is a charming lodging establishment located at 714 Main Street in the picturesque town of Greenport, New York.