Places to stay in Shelter Island, NY

This North Fork waterside flat offers prime waterfront views and is located just 1.5 kilometres from Greenport Village, with easy access to local farm stands and vineyards.
This spacious residence accommodates up to eight guests, featuring four bedrooms, three bathrooms, a fully equipped chef’s kitchen, a sun room, a rec room, and an outdoor patio perfect for enjoying the scenery.

This fully renovated 1860s farmhouse on Shelter Island offers a tranquil retreat, conveniently located near Shelter Island's beaches and restaurants, with easy ferry access from both the Hamptons and the North Fork.
The three-bedroom, two-bathroom property sleeps six guests and boasts a heated pool, jacuzzi, and three fireplaces, alongside modern amenities including a fully equipped kitchen and Wi-Fi.

This charming house is located just a short walk from Greenport's waterfront and a few blocks from the charming downtown area, offering a peaceful retreat close to the action. The property has received excellent ratings for its cleanliness, location, and overall experience.
The house is laid out over two floors and can accommodate up to four guests. Enjoy a fully equipped kitchen, a private patio, and a family room with a sofa bed, plus a two-car driveway, air conditioning, and a garden.

This charming apartment is situated in historic Sag Harbor Village, just a 10-minute walk from the lively Main Street and a 5-minute stroll from the tranquil Bay beach. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment features a private entrance and hallway, ideal for storing bikes and offering privacy. It comfortably accommodates two guests and has a fully equipped kitchen with a fridge and microwave oven. Guests can enjoy beach amenities, including towels, chairs, and an umbrella, and benefit from free parking after September 15th.

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 Shelter Island holiday home, offering 'Stunning Water Views, Huge Pool, Family Resort', is situated near a local beach, a 3km drive away, and 16km from Sag Harbor.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a large deck overlooking a 15-metre heated pool, a landscaped garden, and includes kayaking and fishing equipment for exploring the surrounding area.

This Silver Beach apartment in Shelter Island Heights is near Shell Beach (a short walk) and Sunset Beach (a short drive), with a town landing for kayaking, canoeing and paddle boarding less than 0.4 kilometres away.
The one-bedroom, one-bathroom flat sleeps two guests and offers a private entrance, second-floor balcony with water views, a fully equipped kitchen including a fridge and dishwasher, air conditioning, a garden, and hot and cold outdoor shower.

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 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 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 restored farmhouse is situated in East Marion, just a short walk from the Hampton Jitney, Sep's farm stand, and Angels Market, and within a 10km drive of Greenport Village, Orient, and the Shelter Island Ferry. It enjoys excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The farmhouse offers 251 square metres of space, comfortably accommodating up to 6 guests in its four bedrooms and three bathrooms. The property boasts a modern kitchen, a large garden with a deck, BBQ, and hammock, a heated swimming pool, and ample parking, making it perfect for families and those seeking a relaxing getaway.

This Greenport holiday home enjoys a central downtown location, just 0.16 km from Front and Main Streets and under 0.8 km from the Shelter Island Ferry and the Long Island Rail Road.
The two-bedroom property sleeps six, features a fully equipped kitchen with dishwasher, air conditioning, a garden, parking for two cars, and is within easy walking distance of Greenport's shops, restaurants, and waterfront.