Places to stay in Greenport, NY

This secluded six-acre estate in Shelter Island Heights offers a private retreat, just a short 150-metre walk to Bootleggers Alley beach and a brief drive to Crescent Beach.
This luxurious residence accommodates up to ten guests across two dwellings, featuring five bedrooms and five bathrooms, a chef's kitchen, a heated swimming pool, and a separate guest cottage.

This charming house is situated in Greenport, just a short walk from the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura, offering easy access to the town's attractions. The area is peaceful and provides a relaxed atmosphere.
The house spans 251 square metres (2,700 square feet) and features three bedrooms, three bathrooms, a fully equipped kitchen, and a spacious living area. Guests can enjoy a private pool, a garden, a Jacuzzi, a terrace, barbecue facilities, and free Wi-Fi.

This Sag Harbor contemporary property, located in Noyack, offers easy access to the Hamptons beaches and Cooper's Beach, approximately 8 kilometres from the Sag Harbor Whaling and Historical Museum.
Sleeping up to 14 guests, this four-bedroom, four-bathroom house boasts a spacious layout including a king, queen, twin and full beds, an additional office with a futon, a large open-plan kitchen, outdoor BBQ, and swimming pool.

This Greenport house, situated 0.5 kilometres from Greenport Village centre, offers easy access to local shops, restaurants, beaches, and marinas.
Sleeping six guests, this fully renovated three-bedroom, three-bathroom property boasts a large eat-in kitchen, expansive living room, and private garden, plus a swimming pool and parking.

This family-friendly cottage is situated in the quiet Pipes Cove neighbourhood of Greenport village, offering easy access to the Railroad Museum of Long Island, 4 kilometres from the Greenport Harbor Brewing Company and Kontokosta Winery, and close to kayaking and sailing opportunities.
The 167 square metre property, accommodating up to 8 guests, features 4 bedrooms, 4 bathrooms, a fully fenced garden, a wood-burning fireplace, a gas grill, and a well-equipped kitchen, with parking and Wi-Fi provided.

This eight-bedroom house is located in Northwest Harbor, a short distance from the harbourfront and within easy reach of the town's main attractions. This spacious house boasts a large mahogany sun deck, al fresco dining and lounging spaces, a built-in gas grill, a saltwater gunite pool and spa, a grand play-set, and a fitness centre, perfect for families and groups of up to 13 guests.

This Shelter Island pool house cottage is situated in a tranquil area, minutes from both the North and South ferries and within 2.4 kilometres of key island businesses.
Offering three bedrooms, a private pool house with separate entrance and parking, a king-size bed, full bathroom, kitchenette with Nespresso machine, and access to a shared swimming pool (25 May – 30 September), this property sleeps up to six guests and boasts a fitness centre and excellent user ratings.

This charming house is located in Greenport, a short walk from the Farmers' Market, the Railroad Museum, and the Camera Obscura, making it ideal for exploring the town's attractions. This property has received very good user ratings, indicating a comfortable and enjoyable stay.
The house has three bedrooms, accommodating up to eight guests, and is perfect for families or groups of friends. Amenities include a fully equipped kitchen, a terrace, a garden, and parking, ensuring a comfortable and enjoyable stay.

This Southold holiday home is located just a short distance from a beautiful beach and a short drive from the Peconic Bay Winery and Railroad Museum of Long Island, offering a peaceful escape in a picturesque setting. It has received excellent user ratings, making it a popular choice for travellers.
This spacious property has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The home features a fully equipped kitchen, a jacuzzi, a terrace, a garden, a spa, parking, and a range of outdoor amenities including a hot tub, fire pit, and outdoor shower, perfect for relaxing and entertaining.

This luxury Sag Harbor holiday home, offering 'Luxury Resort-style Retreat In The Heart Of Sag Harbor With Heated Pool...', is a 9-minute walk (approximately 0.8 km) from the Sag Harbor Whaling and Historical Museum and an 11-minute walk (approximately 1 km) from the Old Whalers Church.
The five-bedroom, five-bathroom property boasts a private heated pool, attached garage, fully equipped kitchen, and in-house amenities including a barbecue, fireplace, gym, and billiards table, comfortably accommodating ten guests.

This beachfront house is situated in Greenport, a short distance from the Soundview, offering easy access to restaurants, bars, and the North Fork's wineries, breweries, and farms.
The property, which can accommodate up to eight guests, boasts a private enclosed porch and back deck, providing stunning views of the Long Island Sound, and includes amenities such as paddle boards, bicycles, and beach chairs.

This vacation home is located in Southold, just half a kilometre from The Old Field Vineyards and within a 5-kilometre radius of Sparkling Pointe and Mattebella Vineyards, making it a great base for exploring the region's renowned wineries. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The property spans 325 square metres and comfortably accommodates up to 10 guests. It features a fully equipped kitchen, four bathrooms, a balcony, a Smart TV, a fireplace, and barbecue grills, providing everything needed for a relaxing and enjoyable stay.

This Greenport cottage is located 42 kilometres from Splish Splash and 76 kilometres from Long Island MacArthur Airport.
This spacious 158 square metre holiday home offers three bedrooms, two bathrooms, two living rooms, a dining area, a fully equipped kitchen, an outdoor pool, a sauna, an outdoor dining area, and a patio with a fireplace, accommodating up to 19 guests with a check-out time of 10:00 AM.

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.

This five-bedroom, five-bathroom house in Noyack offers excellent accommodation for up to ten guests, boasting a swimming pool, fitness centre and proximity to Noyack Bay (distance unspecified) for water activities.
The property includes a fully equipped kitchen, ample parking, and a garden, making it ideal for families seeking a comfortable stay near Noyack village centre (distance unspecified) and potential hiking or biking trails (distance unspecified).

This apartment is conveniently located in Greenport, just 1 kilometre from the Greenport Farmers' Market, Camera Obscura, and Greenport Carousel, offering easy access to the town's attractions. The area is known for its charming waterfront setting and relaxed atmosphere.
The apartment is well-equipped with a kitchen featuring an oven, stovetop, microwave, and dishwasher, allowing you to prepare your own meals. Guests also enjoy free self parking and free WiFi in public areas, as well as a TV, ceiling fan, and a shower.