Search Shelter Island, NY accommodations

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 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 newly renovated three-bedroom cottage is situated in the historic district of East Marion, just a short walk from the bay and Long Island Sound beaches, the Jitney stop, and local attractions like the lavender farm, farm stands, and the Fork and Anchor restaurant. The cottage has consistently received excellent ratings for its location, cleanliness, and user experience.
The property spans 204 square metres and comfortably accommodates up to five guests. It features a fully equipped kitchen, a spacious living area, a dining room, a den, a terrace, a garden, and parking. Enjoy the convenience of air conditioning, Wi-Fi, and a beach pass for access to the nearby beaches.

This apartment is located in Shelter Island Heights, just a short bike ride away from the beaches, local farm stands, and a nature preserve, making it a great base for exploring the area. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment has four bedrooms and two bathrooms, comfortably accommodating up to eight guests. It features a spacious yard with plenty of sunshine, a well-equipped kitchen, and a range of outdoor games and activities, ensuring everyone has a fun and relaxing stay.

The Cooper-Burke House is a charming property situated in Sag Harbor's historic district, just a short walk from Main Street and a 12-minute stroll to Haven's Beach. The house consistently receives excellent ratings for its location, cleanliness, and overall experience.
This one-bedroom house spans 139 square metres and comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, a spacious terrace, a garden, a spa, parking, and Wi-Fi access, allowing for a relaxing and enjoyable stay.

This Southold waterfront apartment, situated on Long Creek and Hashamomuck Pond, offers direct water access and is conveniently located near the village centre.
The four-bedroom, three-bathroom dwelling sleeps eight guests and boasts a private deck, hot tub (seasonal), kayaks, paddleboards, a firepit, and ample outdoor space including hammocks.

This Greenport apartment is located a mile from the ferry and 42 kilometres from Splish Splash waterpark, offering easy access to the area's attractions. The property has received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom apartment spans 84 square metres and comfortably accommodates up to six guests. This property features a fully equipped kitchen, air conditioning, a terrace, a garden, and parking, as well as free Wi-Fi.

This 1957 former sweet and soda shop, located in Greenport, New York, offers unique historical character and is situated less than 1 kilometre from the Shelter Island Ferry, 9.6 kilometres from Sparkling Pointe Vineyards & Winery, 12 kilometres from Pindar Vineyards, and under 19.2 kilometres from Orient Beach State Park.
This dog-friendly flat accommodates up to six guests with three bedrooms and three bathrooms, featuring a spacious private garden with provided bicycles, a modern kitchen with marble countertops and stainless steel appliances, air conditioning, two fireplaces, and an in-home washer/dryer.

This Shelter Island Heights ranch house, located in the Silver Beach community, offers direct access to a private beach within walking distance and is a short drive from Sunset Beach, local shops, and restaurants.
The three-bedroom property, sleeping up to eight guests, boasts a fully equipped kitchen, two-and-a-half bathrooms, a deck with outdoor furniture, a gas grill, and a private one-acre garden.

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 two-bedroom cliffside condominium in Greenport offers direct access to the Long Island Sound, placing guests within immediate proximity to local wineries, agricultural farms, and the village centre.
This property accommodates up to six guests and features air conditioning, a swimming pool, a garden, parking, a kitchen equipped with a fridge, microwave, and dishwasher, and provides stunning water views and sunsets.

This two-bedroom apartment is situated on a small bluff overlooking the Long Island Sound, just a short walk from Greenport's town centre and its array of farms, wineries, restaurants, and shops. The apartment offers stunning waterfront views, direct access to a private beach, and a shared pool, perfect for relaxing and enjoying the beautiful surroundings.