Top 30 Best Vacation house rentals 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 Douglas Elliman Real Estate Office in Greenport, NY, where your property dreams become reality.

Welcome to Douglas Elliman Real Estate Office in Cutchogue, NY, your premier destination for all your real estate needs on the North Fork of Long Island.

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.

Welcome to Douglas Elliman Real Estate Office in Mattituck, NY, your premier destination for all your real estate needs on Long Island's North Fork.

Welcome to Signature Premier Properties | Southold, your trusted real estate agency located in the heart of Long Island's picturesque North Fork.

Welcome to Andrea "Andi" Parks @ Douglas Elliman Real Estate, your trusted partner in navigating the vibrant real estate market of Long Island's North Fork.

Welcome to Kristy Naddell Real Estate, your trusted partner in finding the perfect home or property in the heart of Cutchogue, New York.

Welcome to Rita Rooney, Douglas Elliman Real Estate, your trusted partner in navigating the vibrant and diverse real estate market of Greenport, New York.

Welcome to Diane Mollica, Realtor at Compass, your trusted real estate partner located at 54100 Main Road, Southold, New York 11971.

Welcome to Constantino Alves, Real Estate Professional, your premier destination for all your real estate needs in Mattituck, New York.

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.

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.

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

Tapestry House is a charming lodging located at 503 Front Street in the picturesque town of Greenport, New York. This historic institution offers a unique and cozy atmosphere for guests to relax and unwind during their stay.

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 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.

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

Located at 207 Front Street in Greenport, New York, The Menhaden is a charming institution offering a unique blend of bar, food, lodging, and restaurant services.

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 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.