Places to stay in Shelter Island, NY

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 five-bedroom, four-bathroom Bay Point holiday home in Sag Harbor, near Havens House and Sylvester Manor, offers stunning water views and proximity to local attractions.
Sleeping up to ten guests, this property boasts a heated pool, jacuzzi, private dock (accommodating boats up to 40 feet), terrace, rooftop deck, and all modern amenities including a fully equipped kitchen and internet access.

This three-bedroom, two-bathroom house in Shelter Island Heights offers a secluded two-plus acre property bordering a nature preserve, less than 16 kilometres from several beaches and local restaurants.
The property, perfect for six guests, boasts a private heated swimming pool and hot tub (open May 20th to mid-October), a screened porch, patio with barbecue, and ample outdoor space including a hammock and tire swing.

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 five-bedroom house, part of the ‘Shelter Island Getaway! Gourmetkök Och öPpen Spis ... En Vinterresort!’ offer, is located in the peaceful Montclair Colony on Shelter Island, within 5km of Havens House, the Shelter Island Historical Society, Sunset Beach, Shelter Island Whale's Tail, and Crescent Beach.
The property boasts a private pool, four bathrooms, laundry facilities, and can comfortably accommodate eight guests, offering a smoke-free environment and access to a shared outdoor pool.

This East Marion waterfront property boasts a private beachfront location on Gardiner's Bay, a 9.6km drive from Greenport village and 21km from Orient Beach State Park, offering a private mooring.
The self-catering house comprises two houses sleeping eight guests across three bedrooms and three bathrooms, featuring fully equipped kitchens, a dedicated workspace, abundant recreational equipment (kayaks, paddleboards, bikes), and family-friendly amenities (children's bikes, toys, games).

This Greenport holiday home is ideally located less than 0.8km from Greenport Farmers' Market, the Camera Obscura, and the Long Island Railroad Museum, with other attractions such as the East End Seaport Maritime Museum and Greenport Carousel within 1.6km.
The 139 square metre property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped kitchen, private patio, garden, barbecue, free Wi-Fi, and parking.

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 waterfront property is situated on the Menantic Peninsula in Shelter Island Heights, offering a tranquil retreat just a short distance from the charming village centre. The house has received excellent ratings for user experience, location, and cleanliness.
This four-bedroom residence spans 372 square metres and offers a spacious interior with white oak floors, two large balconies with sea views, and a 1/4 kilometre driveway leading to park-like grounds. The property boasts a private sandy beach, a jacuzzi, a fitness centre, a tennis court, and a deep water dock, as well as concierge services and a gourmet kitchen.

This luxurious six-bedroom property in Shelter Island Heights boasts a 465 square metre floor area, situated approximately 6.4 kilometres from Sylvester Manor and 8 kilometres from the Shelter Island Historical Society.
The spacious residence, ideal for large groups, offers a private beach, seasonal swimming pool, fully equipped gym, game room, outdoor kitchen, and ample parking for seven vehicles, alongside kayaks and bicycles for guest use.

This stylish apartment is ideally situated in Sag Harbor, just 1.6 kilometres from both Long Beach and the town centre, offering easy access to the area's attractions. The property has consistently received excellent guest reviews, highlighting its comfortable and well-equipped nature. The apartment offers three bedrooms and three bathrooms, spanning 186 square metres of living space. Guests can enjoy a range of amenities, including a private swimming pool, a terrace with water views, and a fully equipped 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.

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 three-bedroom, two-bathroom New England-style cottage is centrally located in Shelter Island's main village, offering easy access to local shops and restaurants.
Sleeping six guests, this holiday home boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a garden, parking, and excellent guest reviews; nearby beaches and attractions are within easy reach.

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 recently renovated four-bedroom contemporary cottage, situated in Shelter Island Heights, offers easy access to the Shelter Island village, a short ferry trip from Long Island's eastern end.
The property boasts a private gunite pool, large deck backing onto a nature reserve, and use of kayaks and paddleboards at a nearby community beach; it sleeps eight guests and includes a kitchen, air conditioning, internet access, and parking.