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.