Holiday Rentals in Greenport, NY

This coastal condominium, Unit A202, offers convenient proximity to the beach, local dining establishments, and nearby attractions in Greenport.
This apartment sleeps six guests and features two bathrooms, air conditioning, a swimming pool, and a kitchen equipped with a fridge, microwave, and dishwasher, ensuring a comfortable stay with internet access.

This brand new Greenport Village house, a short walk from the shops, restaurants and bars, offers superb access to the town's amenities.
Sleeping fourteen guests across four bedrooms and four bathrooms, this spacious property boasts a year-round heated pool with hot tub, open-plan living space, and modern amenities.

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 Greenport apartment is a 5-minute walk from the bustling Front Street and Main Street, where you'll find shops, restaurants, and bars, and is also located across from a park and playground. The apartment has excellent user, location, and cleanliness ratings.
The apartment has two bedrooms and two bathrooms, accommodating up to five guests. Enjoy the private outdoor dining on the rear deck, relax on the covered front porch, or unwind in the private yard with a BBQ, fire pit, Adirondack chairs, and lounge areas.

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 charming flat is located on a peaceful street in Greenport, just 0.8 kilometres from the town centre with its restaurants, bars, shops and cafes, offering a view of the harbour from both the bedroom and kitchen. It has received excellent ratings for its location, cleanliness and overall experience.
The apartment is perfect for couples, with one bedroom and one bathroom. It comes equipped with air conditioning, parking, a fridge and internet access, and offers a peaceful escape from the hustle and bustle of the town centre.

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 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 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 apartment is located in a high-end development on Long Island Sound, just 2 kilometers from the centre of Greenport. It has consistently received excellent ratings for user experience, location, and cleanliness.
The apartment has two bedrooms and two bathrooms, comfortably accommodating six guests. It offers a range of amenities, including a private balcony with ocean and pool views, access to a private beach, a fully equipped kitchenette, a shared laundry facility, and charcoal grills for communal use.

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 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 two-bedroom house is situated in Greenport, less than 1.6 kilometres from the Greenport Farmers' Market and the Greenport Station, making it a convenient base for exploring the town. The property features a private garden, barbecue grills, and a fully equipped kitchen with a refrigerator, oven, stovetop, and microwave, as well as a spa, terrace, and parking.

Resort listing with an excellent rating of 95% based on 30 reviews. Your accommodation will be located in Greenport.
Services and facilities: a garden, a fridge and a kitchen. Take advantage of the terrace in this resort!

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 modern three-bedroom bungalow in Greenport Village is ideally located less than a kilometre from the beach, the town centre, the Shelter Island Ferry, and the Long Island Railroad.
The property offers a spacious backyard, a master bedroom with an ensuite bathroom and walk-in closets, and a fully equipped kitchen with a fridge, microwave oven, and dishwasher, making it perfect for families or groups of up to five guests.

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 luxurious six-bedroom house in East Marion, New York, is a short walk (1.6km) from Lavender by the Bay and a two-minute drive (1.6km) from a private beach with kayaks and paddleboards.
The 5-bathroom property sleeps up to 13 guests, boasting a heated pool, hot tub, Peloton bike, and fully equipped kitchen, plus outdoor games and a fire pit, all within easy reach of the Antique Carousel and Orient State Park.

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 Greenport house is situated in a residential neighbourhood, just a short walk from the town centre and a 1.5 kilometre drive from the waterfront. The property has received excellent ratings for its location, cleanliness, and overall experience.
The home is spacious and can accommodate up to 10 guests. It offers a fully equipped kitchen, air conditioning, a private garden with a swimming pool, and parking.

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 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 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 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 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 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.