Holiday Rentals in Greenport, NY

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 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.

Vacation resort with an excellent rating of 95% based on 30 reviews. Your accommodation will be based in Greenport.
Services and facilities include a fridge, a kitchen and a swimming pool. Take advantage of the Free Parking with this resort in Greenport!

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 Greenport apartment, conveniently located near a resort with a heated pool and barbecue grills (open Memorial Day to Labour Day), offers a self-catering stay for up to six guests.
The two-bedroom, two-bathroom flat includes a full kitchenette, private balcony, and two parking spaces, providing ample space and essential amenities such as linens and toiletries.

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.

This luxury park model is situated on over 9.1 hectares at the eastern tip of Long Island's North Fork, offering a secluded escape near Greenport.
This two-bedroom, one-bathroom lodge accommodates up to six guests and features air conditioning, internet, a kitchen, and parking, with access to resort amenities including a heated pool and pickleball courts.

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.

Vacation resort with an excellent rating of 95% based on 30 reviews. Your accommodation will be based in Greenport.
Services and facilities include a fridge, a kitchen and a swimming pool. Take advantage of the Free Parking with this resort in Greenport!

This Southold residence offers private beach access, a 5-minute walk or bike ride to August Acres Private Association Beach, and is a 5-kilometre drive from Greenport and Southold.
This four-bedroom, two-bathroom holiday home accommodates up to nine guests and features a heated outdoor swimming pool, four bicycles, a stand-up paddleboard, an enclosed outdoor shower, a fire pit, hammocks, and a basement playroom.

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 Greenport holiday home enjoys a central downtown location, just 0.16 km from Front and Main Streets and under 0.8 km from the Shelter Island Ferry and the Long Island Rail Road.
The two-bedroom property sleeps six, features a fully equipped kitchen with dishwasher, air conditioning, a garden, parking for two cars, and is within easy walking distance of Greenport's shops, restaurants, and waterfront.

This beachfront cottage in Southold offers direct access to a private community beach and overlooks Goose Creek, with Croteaux Vineyards and the Railroad Museum of Long Island within a 5 kilometre drive.
This renovated 3-bedroom, 2-bathroom property sleeps up to six guests and features a well-equipped kitchen, air conditioning, a garden, spa, parking, and is ideal for activities such as boating, fishing, and birdwatching.

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.