Greenport Vacation Rental Homes By Owner

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique... Read More

Walk to the beach, shelter island ferries, LIRR, Hampton jitney, restaurants, shops. Or take one of our bicycles! Comfort in our king beds with plenty of space.... Read More

Waterfront Water's Edge luxury suite, Suite C-204 accommodates up to 6 guests (See below) with two bedrooms and two bathrooms located on the North Fork of Long... Read More

Family friendly cottage, nestled in a quiet street in Greenport village. The private property has fully fenced backyard, 4 bedrooms, 4 bathrooms, outdoor shower,... Read More

Charming 2-bedroom cottage located on a family-owned waterfront estate that was converted from a circa 1920s chicken coop. This retreat has inspiring views of... Read More

The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern and tasteful American Beech Boutique... Read More

Tranquil 2021 renovated and centrally located cottage. Professionally designed for peaceful comfort and enjoyment. Soak up the bright light provided by skylights... Read More

Newly renovated and charming ranch home in the NorthFork, a short walk to the village of Greenport, vineyards, and the breathtaking 67 Steps beach, among other... Read More

3 bedroom with deeded beach rights and partial water view. 5 minute walk to the beach and short drive to the heart of the village. Vineyards, farms, and other... Read More

Greenport Getaway Newly built ranch, beautifully landscaped with pool, large yard, patio, fire pit, ample seating, minutes to private beach 3BR/2BA: open floor... Read More

Located on a family-owned waterfront estate, The Gate House, a cozy 2-story, 2-bedroom cottage, is only steps away from the tranquil waters of the Peconic bay.... Read More

Gorgeous 4 bedroom, 3.5 bath house with a fenced in pool, primely located close to everything Greenport has to offer & in a quiet development. This beautiful... Read More

The perfect getaway. Within walking distance to beach, town, Jitney, LIRR and ferries to the South Fork. This quiet and bright house is located in the heart of... Read More

Spacious Greenport 2600 square foot Four home. Less than a mile walking distance to Greenport Village (restaurants, bars, coffee shops, shopping and much more)... Read More

GREENPORT CONKLING PT CREEKFRONT MINT 3BR COTTAGE W/PRIME VIEWS - This cottage on a half-acre lot fronts on the pristine creek inside Conkling Point with one of... Read More

Combine peace and quiet with bustling downtown action when you book this charming Greenport vacation rental! The 1-bedroom, 1-bath apartment sits on a peaceful... Read More

Home has a full kitchen and a washer/dryer. There are two bedrooms with queen size beds plus a Murphy double bed. One bathroom is en suite with a shower. The... Read More

A quiet Cape home within walking distance to all Greenport Village has to offer - dining, shopping, the beach and transportation hub. A perfect getaway for... Read More

Spend your summer days in Long Island as you relax in 'Jason's Haven,' a 3-bedroom, 1-bathroom vacation rental home that sleeps 6. Nestled within the historical... Read More

Luxury home with beautiful marina views. This 1860’s custom Victorian Farmhouse has been fully renovated with all modern amenities. Gorgeous chefs kitchen,... Read More