Holiday Rentals in Greenport, NY

This charming house is situated in Greenport, just a short walk from the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura, offering easy access to the town's attractions. The area is peaceful and provides a relaxed atmosphere.
The house spans 251 square metres (2,700 square feet) and features three bedrooms, three bathrooms, a fully equipped kitchen, and a spacious living area. Guests can enjoy a private pool, a garden, a Jacuzzi, a terrace, barbecue facilities, and free Wi-Fi.

Vacation resort listing with an excellent rating of 95% based on 30 reviews. This accommodation is located in Greenport.
Services and facilities: a terrace, air conditioning and a barbecue.

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.

This charming cottage is located just a short walk, around 800 metres, from the heart of Southold, with its shops, restaurants, and the LIRR train station. The property has received excellent ratings for its cleanliness, location, and overall experience.
The cottage offers two bedrooms, sleeping up to four adults and two children, making it perfect for families or groups of friends. The property benefits from a private garden, a fire pit, and a modern kitchen, as well as being close to local wineries and a brewery.

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 house, situated 0.5 kilometres from Greenport Village centre, offers easy access to local shops, restaurants, beaches, and marinas.
Sleeping six guests, this fully renovated three-bedroom, three-bathroom property boasts a large eat-in kitchen, expansive living room, and private garden, plus a swimming pool and parking.

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 newly built ranch is located centrally in Greenport, a short distance from a private beach and local shops, offering a relaxed atmosphere close to the allure of the Hamptons.
This three-bedroom, two-bathroom residence sleeps six guests and features a heated outdoor swimming pool, a landscaped garden with a fire pit, a wood-burning fireplace, and a fully equipped kitchen.

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 four-bedroom house on Shelter Island, off the eastern end of Long Island, New York, offers easy access to attractions such as the Greenport Carousel and Railroad Museum and is a short ferry journey from Greenport village.
The property sleeps up to 14 guests in a variety of bed types, including a queen, twin, and full-size bed, and features a microwave, air conditioning, Wi-Fi, and two bathrooms; local insider tips are provided by the hosts.

This waterfront property is located in Orient, just under 5 kilometres from Oysterponds Historical Society, Island's End Golf & Country Club, and Truman's Beach, offering a peaceful escape from the hustle and bustle of city life. It has received excellent user ratings, making it a popular choice for travellers.
This three-bedroom house comfortably accommodates up to six guests, perfect for families or groups. The property boasts a range of amenities including a swimming pool, tennis court, and a fully equipped kitchen, as well as a game room for entertainment, ensuring a comfortable and enjoyable stay.

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.

This family-friendly house in Shelter Island Heights is situated a short distance (approximately 0.32 km) from Shelter Island's beautiful beaches.
The three-bedroom, two-bathroom property sleeps six, boasts a spacious open-plan living area, basement playroom, extensive garden with amenities including beach gear, bicycles, and a Big Green Egg smoker, and offers additional sleeping for larger groups (up to £80 per person per night).