Places to stay in Greenport, NY

This renovated 1,900 sq ft flat offers a modern rustic style and is situated a short drive or 1.2 kilometre walk from Greenport's town centre, ferry, train, and jitney.
The property features 2 bedrooms and 2 bathrooms for up to 4 guests, with amenities including air conditioning, a seasonal heated swimming pool (May-September), a garden with a fire pit and koi pond, a fully equipped kitchen, and an indoor fireplace.

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 recently renovated modern farmhouse in Greenport is located less than 1 kilometre from Eastern Shores private beach and within easy walking distance to Greenport Village centre.
This spacious four-bedroom, two-bathroom holiday home offers a large heated saltwater pool, a fully stocked luxury kitchen with high-end appliances, a third-floor TV and game room, and extensive outdoor living spaces, all within proximity to local attractions such as Orient Beach State Park.

This apartment is situated in Southold, just 2.4 km from Greenport Village and 4 km from the centre of Southold, offering a peaceful and secluded location. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The self-catering accommodation can sleep up to six guests in its three bedrooms and two bathrooms. The apartment offers a range of amenities, including a private heated swimming pool, a garden, a BBQ grill, kayaks, bikes, and a private bay beach access, providing ample opportunities for relaxation and exploration.

This spacious Greenport dwelling, a short 0.8-kilometre walk from Greenport's main street and the train/Jitney stop, offers easy access to the waterfront and local amenities.
Sleeping eleven guests comfortably, the property boasts six bedrooms, three bathrooms, two kitchens, two living rooms, a private pool, and a garden, plus in-house laundry facilities.

This spacious Greenport house, less than 1.6km from Youngs Point beach and a short walk from Greenport village centre and American Beech, offers easy access to local amenities and attractions.
The 186-square-metre property boasts four bedrooms sleeping eight, a fully equipped chef's kitchen, Weber gas grill, sauna, and private backyard with screened porch and parking for two cars.

This Shelter Island Heights property is situated a short distance from Pipes Cove and its private beach access for residents, with Greenport and Southold, known for their wineries, just minutes away by car (approximately 1.6 to 3.2 km).
This four-bedroom, three-bathroom house offers stunning Peconic Bay and Shelter Island views, sleeps up to ten guests, and includes a fully equipped kitchen, air conditioning, a garden, parking, and on-site kayak launch facilities.

This Southold beachfront property boasts 100 feet of private Long Island Sound access, a short drive from renowned vineyards such as One Woman, Kontakosta, and The Old Field.
This four-bedroom, two-bathroom house sleeps eight guests and offers a fully equipped kitchen, air conditioning, Wi-Fi, and parking; enjoy stunning sunset views and various water activities directly from the property.

This Shelter Island Heights holiday home, near Crescent Beach and a short drive from the Pridwin Hotel and Leon's restaurant, offers private beach access ideal for swimming, kayaking, and paddleboarding.
The 206 square metre property boasts three bedrooms, three bathrooms, sleeping up to ten guests, and features a fully equipped kitchen, spa, multiple decks, and a finished basement.

This Southold holiday home, situated steps from a private beach and opposite a North Fork vineyard, offers direct access to Shelter Island via a short 5-minute ferry ride.
This five-bedroom, four-bathroom property boasts 270 square metres of living space, encompassing multiple living areas, a fully equipped gourmet kitchen, and a terrace with stunning Peconic Bay views; it comfortably sleeps ten guests and includes kayaks, bicycles, and beach equipment.

This luxury apartment in Shelter Island Heights offers private access to a community beach, swimming area, dock, and kayak storage, and is a short walk or drive from Crescent Beach, Sunset Beach, Wades Beach, and dining at The Pridwin and Leon.
Spanning 195 square meters, this property accommodates up to six guests across four bedrooms, including a finished basement with a queen pullout sofa, and features a chef's kitchen, multiple decks, and a screened-in porch for enjoying the coastal air.

This house is located in Greenport, within a 1.6 km walk of Eastern Long Island Hospital and Stony Brook Eastern Long Island Hospital, and a 2.4 km walk from the Greenport Farmers' Market, Camera Obscura, and Greenport Carousel. Greenport Station is a 2.2 km walk away, making it easy to explore the town and surrounding areas. The house has received excellent ratings for location, cleanliness, and overall user experience, indicating a comfortable and enjoyable stay.
This property offers a spacious living area, a fully equipped kitchen, a garden, and a terrace. Enjoy amenities such as a swimming pool, a spa, parking, and free Wi-Fi, perfect for a relaxing and enjoyable getaway.

This four-bedroom Greenport holiday home is situated on a secluded 3.8-acre plot near Gull Pond, a 5-minute drive (approximately 3.2km) from Greenport's maritime village and local beaches.
The spacious property, boasting a saltwater pool (opening August 2025), hot tub, air hockey, and foosball, comfortably accommodates nine guests and features two separate TV rooms.

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.

This two-bedroom flat is situated just 320 metres from the centre of Greenport, making it a convenient base for exploring the town's shops, restaurants and attractions.
The property features a modern kitchen with stainless steel appliances, a private balcony and a pet-friendly environment, perfect for a family getaway.

This East Marion flat offers panoramic Peconic Bay views and is located less than 3.2 kilometres from historic Greenport, providing convenient access to the East End Seaport Maritime Museum and the Railroad Museum of Long Island.
This three-bedroom, three-bathroom residence accommodates up to six guests and features a wrap-around deck with a barbecue, exclusive access to Truman Beach, and is equipped with air conditioning, Wi-Fi, and a full laundry room.