Vacation Rentals in Greenport, NY

This Greenport holiday home is situated in the desirable Pipes Cove area, a short walk (less than 1.6km) from Greenport's Railroad Museum and East End Seaport Maritime Museum, and within 1.6km of the Camera Obscura and Greenport Carousel.
This 79 square metre property sleeps four guests in three bedrooms and one bathroom, offering a fully equipped kitchen, private patio, swimming pool, spa, and free Wi-Fi; it's also pet-friendly.

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 house is located in Greenport, a short walk from the Farmers' Market, the Railroad Museum, and the Camera Obscura, making it ideal for exploring the town's attractions. This property has received very good user ratings, indicating a comfortable and enjoyable stay.
The house has three bedrooms, accommodating up to eight guests, and is perfect for families or groups of friends. Amenities include a fully equipped kitchen, a terrace, a garden, and parking, ensuring a comfortable and enjoyable stay.

This Southold village property is situated on a half-acre plot, just a short walk from local shops and within easy reach of vineyards, bay and sound beaches. The accommodation has consistently received excellent guest reviews, highlighting its appeal for travellers seeking a peaceful retreat.
This three-bedroom, two-bathroom house spans 204 square metres and offers a spacious, modern and comfortable stay. Guests can enjoy the expansive garden, relax on the terrace or balcony, and benefit from a fully equipped kitchen, air conditioning and free parking.

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 Greenport apartment is located in a quiet residential area, just a short walk from the waterfront and a few blocks from the charming downtown area with its shops and restaurants. It has received excellent ratings for its cleanliness, location, and overall experience.
The apartment has two bedrooms, two bathrooms, and can comfortably accommodate up to six guests. It comes equipped with a kitchen, dishwasher, air conditioning, and a private garden, as well as access to a swimming pool and parking.

This coastal flat, Unit B208, in Greenport provides direct beach access, placing you steps from the sand and sea with sweeping water views from a private balcony.
The accommodation sleeps up to four guests across two bedrooms, featuring a king-size bed and two twin beds, with two full bathrooms and a kitchenette, plus air conditioning and a communal swimming pool.

This apartment is situated on a high bluff overlooking Dering Harbor, just a short walk from the ferry for exploring Greenport and beyond, and only 500 metres from Marie Eiffel for lunch or breakfast.
The apartment is a comfortable one-bedroom property, ideal for a couple, and features a fully equipped kitchen, a spacious living area and a cosy porch with stunning water views. You'll have access to a swimming pool, a fitness centre, parking, and a garden, as well as high-speed internet for those who need to work remotely.

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.

The Chequit is located in Shelter Island Heights, a short drive from the Shelter Island Country Club and Sylvester Manor, and within easy reach of Sunset Beach and Crescent Beach. The peaceful environment of Shelter Island Heights makes this hotel a great choice for travellers seeking a break from the hustle and bustle of city life.
The hotel offers 35 guest rooms, each equipped with blackout drapes/curtains, complimentary wireless internet access, and bathrooms with showers. The Chequit also has a restaurant, a coffee shop/cafe, and free self parking.

This charming cottage in Greenport is situated just a short walk from the harbour and the town centre, offering easy access to restaurants, shops and local attractions. It has received excellent ratings for location, cleanliness and overall experience.
The cottage has three bedrooms and one bathroom, comfortably accommodating up to six guests. It features a fully equipped kitchen, a garden, a BBQ grill, outdoor furniture, a fire pit, and Adirondack chairs, making it perfect for relaxing and enjoying the outdoors.

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 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.