Places to stay in Shelter Island, NY

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 Sag Harbour flat is situated in a peaceful, wooded area, offering proximity to Long Beach and Serene Green Farmstand, and is a short drive to Sag Harbour Village and the Bridgehampton shuttle.
This no-frills accommodation sleeps up to six guests with three bedrooms and one bathroom, featuring air conditioning, a kitchen with a freezer, on-site laundry, and garden access, with beach chairs provided for your convenience.

This Sag Harbour holiday home is a short 0.8km walk from Havens Beach and the Hamptons Beaches, with Sag Harbour Marine Park and Bay Street Theatre within a 2.4km radius.
This three-bedroom, one-bathroom property sleeps six guests and boasts a fully equipped kitchen including a dishwasher, a terrace, garden, and smart TV, offering easy beach access and proximity to local attractions.

This three-bedroom, two-bathroom house on Shelter Island, New York, is situated less than 0.4 km from South Ferry and a 15-minute walk from Wades Beach, offering easy access to Sag Harbour (under 1.1 km by ferry).
The recently renovated property, boasting a spacious 0.4-hectare plot, includes a large bluestone patio with outdoor shower, Brown Jordan furniture and gas grill; it sleeps six guests and features a fully equipped kitchen, central air conditioning, radiant floor heating, and a welcome bottle of Prosecco.

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 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 three-bedroom flat is located in South Ferry Hills on Shelter Island, offering a secluded half-acre setting within walking distance of a private beach and close to the trails of Mashomack Preserve.
This residence accommodates up to six guests with air conditioning and internet, providing a quiet, private, and restorative environment just minutes from ferries to the Hamptons and Greenport.

This Noyack apartment, a short 16km drive from Sag Harbor, Southampton, and Bridgehampton, offers easy access to the Hamptons' attractions.
The self-contained flat sleeps two, features a kitchen, air conditioning, parking, and Wi-Fi, plus access to stand-up paddleboards and canoes, and a nearby dog-friendly beach.

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 built Shelter Island Heights cottage boasts direct dock access and is conveniently located near the island's attractions, though precise distances aren't specified.
The one-bedroom property sleeps four, featuring a queen bed, queen sleeper sofa, dishwasher, air conditioning, kayaks, paddleboards, and an outdoor shower; parking is also available.

This Sag Harbor flat, a five-minute walk from a private beach and a 1.6km stroll or drive from Sag Harbor's Main Street, offers convenient access to both seaside relaxation and the town's amenities.
The self-contained apartment features a two-storey layout with one bedroom, one bathroom, sleeping up to two guests, and includes private parking, plus an electric stove top, and the option for interaction with the homeowners.

This detached house in Noyack offers a unique location within a wooded area, conveniently situated 1.9 kilometres from Foster Memorial Beach.
This property boasts 149 square metres of floor area, accommodates up to 13 guests with 1 bedroom and 3 bathrooms, and features a private swimming pool, kitchen, air conditioning, WiFi, and private parking with an electric vehicle charging point.