Compare Vacation Rentals & Airbnb in Shelter Island, 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 beach house is located in Hay Beach, a neighbourhood on Shelter Island, just a short distance from Menhadden Lane Beach and Mashomack Preserve, offering easy access to local attractions. The house enjoys an excellent user rating, making it a popular choice for travellers.
The two-storey property spans 379 square metres and comfortably accommodates up to 10 guests. The house features a range of amenities, including a private beach, a dock, bikes, a grill, WiFi, games, TV, internet, and an Xbox, making it ideal for families and groups looking for a relaxing and enjoyable stay.

This Noyack house, a short walk from Long Beach and one minute from the Serene Green market, offers easy access to local amenities and the coast.
Sleeping six guests across three bedrooms and two bathrooms, this property boasts a fully equipped kitchen with fridge, freezer, and dishwasher, air conditioning, a garden, parking, and excellent sunset views from its front deck.

This traditional Hamptons beach house is located just 800 metres from Sag Harbor town centre and a short walk from Havens Beach on Sag Harbor Bay, offering a peaceful retreat close to local amenities. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property has four bedrooms and three bathrooms, comfortably accommodating up to 12 guests. Amenities include a private swimming pool, hot tub, fully equipped kitchen, fitness centre, and a beautiful garden with outdoor games and a hammock for relaxation.

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 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 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 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 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 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.

Cliffside Resort Condominiums, a Greenport aparthotel, offers direct beach access and is situated within 4.8 kilometres of Kontokosta Winery, 67 Steps Beach, and Norman E. Klipp Marine Park.
This resort provides pet-friendly apartments with air conditioning, Wi-Fi, swimming pool, garden, parking, and furnished balconies, featuring fully equipped kitchenettes, two bathrooms, and a seating area, with barbecue grills and a picnic area available for guests.

This East Marion flat is situated a 7-minute walk from Island's End Golf and Country Club and a 2-minute drive from Kontokosta Winery, offering convenient access to local attractions.
This 4-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a well-equipped kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, and on-site parking, with a barbecue grill available for outdoor cooking.

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.

Villa Ebrar, situated in Sag Harbor, Noyack, is 3 km from Foster Memorial Beach, 32 km from Montauk Point Lighthouse, and 40 km from the Second House Museum.
This luxury property boasts 279 square metres of living space, offering four bedrooms, three bathrooms, a private indoor pool, a tennis court, and free bikes for exploring the scenic Sag Harbor area, comfortably accommodating large families or groups.

This Sag Harbor holiday home, near Bay Street Theatre and the Sag Harbor Whaling and Historical Museum in North Haven, offers convenient access to other local attractions such as Eastville Heritage House and Havens House.
The five-bedroom, six-bathroom property sleeps ten guests, boasting a private guest area, upstairs sitting room, smart TVs in all bedrooms, a fenced gunite swimming pool, and parking; microwave and dishwasher are included in the kitchen.

This Southold holiday home, a beautifully restored saltbox house, is situated near a nature reserve, vineyards, and breweries, approximately 8km from Greenport Village and Southold.
The three-bedroom property sleeps five, boasting a well-equipped kitchen with high-end appliances, two bathrooms (one with a clawfoot tub and heated floors), outdoor recreation equipment (kayaks, bikes), and a one-acre garden with a fire pit and lawn games.