Southold: Vacation Rental By Owner

Enjoy incredible views and relax in privacy. (small dogs ok! NO CATS) This home also includes full kitchen, yard, laundry room, garage, TV with cable, central... Read More

Located in the heart of wine country, steps from a private beach, minutes to Greenport and the Orient Point ferry. These are just a few of the many attractions... Read More

We bought our wonderful house four years ago and have made many important renovations. Our most important, a new salt water swimming pool with hot tub, will start... Read More

This 2 Bedroom 1 Bath Cottage is Convenient To Downtown Southold & Greenport, Vineyards, Beaches And Restaurants. Steps to the Breathtaking Kenny's Beach, and... Read More

Newly renovated! We've been doing North Fork vacation rentals since 2016 and this is our newest addition. We'd love to have you stay with us! This beautiful home... Read More

Peaceful pondfront cottage with two bedrooms , 1 1/2 baths, pull out couch in Living room can sleep two more , and lovely screened in front porch to enjoy the... Read More

Classic Southold Country Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click... Read More

This stunning luxury home is everything you could possibly want in a vacation rental! -6 Bedrooms -4 Bathrooms -Huge 2 Acre Yard -Over sized pool with a built in... Read More

North Fork Waterfront Spectacular Views Cottage circa 1930' On Golden Pond' Private road, amazing waterfront view, 100+' water front, shallow calm... Read More

Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, this light and airy 4 bedroom, 2.5 bath... Read More

Two bedroom PERFECT beach house located on a private beach. If you love the beach, fishing, swimming and sunsets in a quiet place, this is for YOU. This is NOT a... Read More

This 3 bedroom 2 bathroom Ranch with open floor plan is just a short distance to one of the nicest and sandiest beaches on the North Fork with the most amazing... Read More

Beautifully remodeled three bedroom two full baths north fork Vacation home just a one minute drive into town and right around the corner to the beach. Everything... Read More

Enjoy the best the North Fork has to offer while staying at our tranquil and peaceful home! Our 3 bedroom, 2 bathroom home is surrounded by award winning... Read More

Enjoy this comfortable farmhouse with six bedrooms, living room, full formal dinning room for 10, eat in kitchen, wrap around porch and large backyard with fire... Read More

Waterfront (with dock) beach house located on Goose Creek, Southold (North Fork, LI). This custom-built new construction (2014) 2,000 sq.ft. home exudes that... Read More

Welcome to the NOFO—where you'll be greeted by beautiful beaches, dozens of wineries and some of the best cuisine New York has to offer! And welcome to our home:... Read More

Relax with the whole family at this peaceful home on the North Fork. Easy walk to private beach or stay and enjoy the water views. This house is airy with big... Read More

This home was built in 2000 and has all the amenities for entertaining. Outside is a new in ground pool, fire pit and outdoor kitchen with a wine bar. Inside... Read More

Beautiful 1-acre waterfront retreat in Harbor Lights neighborhood of Southold. This 4,000 sq ft open concept home has expansive views out to the bay through... Read More