Vacation Rentals in Greenport, NY

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 historic Dutch Colonial house is located in the heart of Greenport's historic district, just a short walk from the town's restaurants, shops, and transport links, including the bus, train, and ferry terminal. Beaches on both Long Island Sound and the bay are less than 1.6 kilometres away. The property has excellent user, location and cleanliness ratings.
The house offers five bedrooms and two bathrooms, comfortably accommodating up to eight guests. The well-equipped kitchen, multiple outdoor spaces, and family-friendly amenities make this a perfect choice for a relaxing getaway.

This charming farmhouse is located just 1.6 kilometres outside of Greenport's town centre, offering sweeping views over the Island's End Golf & Country Club. The property has received excellent ratings for its cleanliness, location and overall user experience.
This spacious property provides three bedrooms and three bathrooms, comfortably accommodating up to nine guests. Enjoy a range of amenities, including a private patio, fenced yard, a game room with a pool table, and a kitchen equipped with a fridge, freezer, microwave oven and dishwasher.

This charming house is located just 1 kilometre from Greenport's vibrant waterfront, with easy access to the Farmers' Market, Camera Obscura, and the Maritime Museum. It has received excellent ratings from previous guests, making it a popular choice for travellers.
The property has 4 bedrooms, comfortably accommodating up to 10 guests. Guests can enjoy the spacious garden, relax on the terrace, and make use of the modern kitchen, complete with a dishwasher, microwave, and fridge.

This holiday home is situated on a peaceful street in Shelter Island Heights, just a short stroll from Sunset, Silver, and Shell beaches. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has a spacious layout that can accommodate up to eight guests. It features a range of amenities including a heated saltwater pool, a hot tub, a fully equipped kitchen, and three dedicated workspaces.

This four-bedroom, four-bathroom house in Greenport, on New York's North Fork, offers easy access to Shelter Island Heights via ferry or bridge (exact distances unspecified), and is a short drive from Southold.
The property boasts a private heated pool and hot tub, spacious living areas accommodating eight guests, a gourmet kitchen, dedicated workspace, ample parking, and outdoor amenities including a deck and gas BBQ; nearby beaches include HOA Beach, 67 Steps Beach, Sandy Beach, and Southold Town Beach (distances unspecified).

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 Greenport apartment is located in the Cliffside Resort Condominiums on the North Fork of Long Island, just a short walk from the beach. The apartment has excellent user, location, and cleanliness ratings.
The apartment, which is 65 square metres in size, has two bedrooms, two bathrooms, and can accommodate up to six guests. It offers a range of amenities including a private balcony and deck, a well-equipped kitchenette, and access to a private beach, swimming pool, and spa.

This luxury apartment in Shelter Island Heights offers private access to a community beach, swimming area, dock, and kayak storage, and is a short walk or drive from Crescent Beach, Sunset Beach, Wades Beach, and dining at The Pridwin and Leon.
Spanning 195 square meters, this property accommodates up to six guests across four bedrooms, including a finished basement with a queen pullout sofa, and features a chef's kitchen, multiple decks, and a screened-in porch for enjoying the coastal air.

This East Marion flat is situated a 7-minute walk from Island's End Golf and Country Club and a 2-minute drive from Kontokosta Winery, offering convenient access to local attractions.
This 4-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a well-equipped kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, and on-site parking, with a barbecue grill available for outdoor cooking.

This beachfront house is situated in Greenport, a short distance from the Soundview, offering easy access to restaurants, bars, and the North Fork's wineries, breweries, and farms.
The property, which can accommodate up to eight guests, boasts a private enclosed porch and back deck, providing stunning views of the Long Island Sound, and includes amenities such as paddle boards, bicycles, and beach chairs.

This Greenport apartment is located a mile from the ferry and 42 kilometres from Splish Splash waterpark, offering easy access to the area's attractions. The property has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom apartment spans 84 square metres and comfortably accommodates up to six guests. This property features a fully equipped kitchen, air conditioning, a terrace, a garden, and parking, as well as free Wi-Fi.

This Greenport holiday home, a converted 1870s schoolhouse, is conveniently located near Greenport village, Kontokosta Winery, and Safe Harbor Stirling.
Sleeping seven guests across three bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen, a large private garden with a deck, fire pit and hammock, plus in-home entertainment including a Roku TV and games consoles.

This family-friendly cottage is situated in the quiet Pipes Cove neighbourhood of Greenport village, offering easy access to the Railroad Museum of Long Island, 4 kilometres from the Greenport Harbor Brewing Company and Kontokosta Winery, and close to kayaking and sailing opportunities.
The 167 square metre property, accommodating up to 8 guests, features 4 bedrooms, 4 bathrooms, a fully fenced garden, a wood-burning fireplace, a gas grill, and a well-equipped kitchen, with parking and Wi-Fi provided.

This Pipes Cove holiday home is conveniently located less than 0.5km from the Railroad Museum of Long Island and East End Seaport Maritime Museum, and within 1km of Greenport Carousel and Camera Obscura, with Greenport Station a short 3-minute walk away.
The 74 square metre property sleeps six guests in three bedrooms and one bathroom, offering a fully equipped kitchen, jacuzzi, terrace, garden, parking, and free Wi-Fi; barbecue grills are available for outdoor dining.

This newly renovated Greenport house, situated just blocks from Main Street and a short 1.6km drive from Greenport's beaches, offers convenient access to restaurants, bars, the Hampton Jitney, Long Island Rail Road, and Shelter Island Ferry.
The three-bedroom, two-bathroom dwelling sleeps eight guests and boasts a high-end kitchen (Sub-Zero, Wolf, Bosch appliances), smart TVs, central air conditioning, a spacious fenced garden, and ample parking.