Vacation Rentals in Greenport, NY

This two-bedroom cliffside condominium in Greenport offers direct access to the Long Island Sound, placing guests within immediate proximity to local wineries, agricultural farms, and the village centre.
This property accommodates up to six guests and features air conditioning, a swimming pool, a garden, parking, a kitchen equipped with a fridge, microwave, and dishwasher, and provides stunning water views and sunsets.

This modern cottage, offering a secluded luxury escape, is situated on over 23 acres at the easternmost tip of Long Island's North Fork, providing private access to both indoor and outdoor spaces.
This 2-bedroom, 1-bathroom dwelling accommodates up to 4 guests and features air conditioning, Wi-Fi, a fully equipped kitchen, a grill, and a fire pit, with access to resort amenities including a heated pool and pickleball courts.

This recently renovated two-bedroom flat offers direct access to Greenport Village beach and is within a 500-meter walk of Greenport's town centre, making it an ideal base for exploring the North Fork's wineries and attending local events.
This accommodation accommodates up to eight guests and features two bedrooms with king-size beds, a kitchen, air conditioning, and complimentary internet, with secure keyless entry provided.

This three-bedroom house is situated in central Greenport, just under a kilometre from the Greenport Farmers' Market, the Railroad Museum of Long Island, and the Camera Obscura.
The property is ideal for families or groups of up to six, with a fully equipped kitchen, a garden, and parking available.

This four-bedroom Shelter Island house, situated on Menantic Creek, is a six-minute drive from the Shelter Island Ferry.
The property boasts a fully equipped kitchen, laundry facilities, kayaks, paddleboards, and bicycles, accommodating up to ten guests in its spacious layout, and includes a home office.

This newly finished modern cottage in Greenport is located within easy reach of the village and its attractions.
This one-bedroom, one-bathroom cottage sleeps up to four guests and features a fully equipped kitchen, air conditioning, a swimming pool, a garden, and outdoor seating with a grill and fire pit.

This Greenport holiday home is ideally located less than 0.8km from Greenport Farmers' Market, the Camera Obscura, and the Long Island Railroad Museum, with other attractions such as the East End Seaport Maritime Museum and Greenport Carousel within 1.6km.
The 139 square metre property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, private patio, garden, barbecue, free Wi-Fi, and parking.

This Greenport apartment, situated less than 0.32 kilometres from Greenport Village, offers easy access to shops, restaurants, beaches, Mitchell Park's antique carousel, and the Shelter Island ferry.
The two-bedroom flat, sleeping up to three guests, includes a full kitchen, dining room, private parking, and a private upstairs deck; enjoy nearby activities such as exploring the village, relaxing on the beach, or taking a ferry trip to Shelter Island.

This restored farmhouse is situated in East Marion, just a short walk from the Hampton Jitney, Sep's farm stand, and Angels Market, and within a 10km drive of Greenport Village, Orient, and the Shelter Island Ferry. It enjoys excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The farmhouse offers 251 square metres of space, comfortably accommodating up to 6 guests in its four bedrooms and three bathrooms. The property boasts a modern kitchen, a large garden with a deck, BBQ, and hammock, a heated swimming pool, and ample parking, making it perfect for families and those seeking a relaxing getaway.

This apartment is situated in Greenport, just under 2.5 miles from the town centre and a short drive from the historic Hortons Point Lighthouse. The apartment has received excellent ratings for its location, cleanliness and overall experience.
The two-bedroom apartment is 51 square metres in size and offers a range of amenities including a private balcony with sunset views, access to a private beach, a swimming pool, a garden, parking, and a modern kitchen.

This century-old shingle house, an idyllic waterfront property, offers picturesque views of a tidal creek flowing into Dering Harbor, situated on Shelter Island.
This spacious four-bedroom residence accommodates up to eight guests, boasting a well-equipped kitchen, air conditioning, and outdoor living areas including a deck and a cedar-fenced patio with a Weber gas grill, providing direct deck access to a large family room with water views.

This three-bedroom, two-bathroom house in Hay Beach, Shelter Island Heights, is located a short 6.4km drive from Gardiner's Bay Country Club and Shelter Island Whale's Tail Recreation Park.
The property sleeps six guests and boasts a fully equipped kitchen with dishwasher and microwave, in-unit laundry facilities, Wi-Fi, air conditioning, and on-site parking, plus access to BBQ grills and a fitness centre.