Holiday Rentals in Greenport, NY

This newly finished modern cottage in Greenport is located within easy reach of the village and its attractions.
This one-bedroom, one-bathroom cottage sleeps up to four guests and features a fully equipped kitchen, air conditioning, a swimming pool, a garden, and outdoor seating with a grill and fire pit.

This Southold villa, situated on a private one-acre compound, offers seclusion yet proximity to Southold village and the Long Island Sound (distances unspecified).
The three-bedroom, four-bathroom property sleeps six guests and boasts an infinity-edge saltwater pool, oversized spa, outdoor wood-fired pizza oven, and private garden with organic produce, alongside Tuscan-inspired exterior and modern Hamptons interior design.

This Greenport apartment, situated on a bluff overlooking the Long Island Sound, offers stunning waterfront views and is minutes from the town centre with its shops and restaurants.
The two-bedroom, two-bathroom flat sleeps six guests, boasting a king suite, twin bedroom, sleeper sofa, private beach access, a shared pool, and amenities including smart TVs, a record player, and a well-equipped kitchenette with a wine cooler.

Arthur's Vineyard, a 1905 farmhouse in Greenport, New York, is a 10-minute walk from Greenport village's beaches, marina, restaurants, boutiques, and train station, and a short drive from North Fork wineries and farm stands.
This three-bedroom, two-bathroom property sleeps six, features a well-equipped kitchen, a wood-burning fireplace, a landscaped garden, and a fitness centre, offering guests a blend of historic charm and modern comfort.

This modern farmhouse is situated in Orient, New York, just a short walk from the historic Village Lane "town" center and the beautiful Youngs Road beach, offering easy access to both the village's amenities and the beach's natural beauty. This property has received excellent ratings for its location, cleanliness and overall experience.
This spacious home, with 4 bedrooms and 4.5 bathrooms, comfortably accommodates up to 8 guests. Enjoy a range of amenities, including a private saltwater pool, a fully equipped kitchen, high-speed internet, and a garden, as well as bikes, ping pong, and sports equipment for enjoying the local area.

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 Greenport apartment, located in the Historic Maritime Village, is a short 0.32-kilometre walk from Greenport Village's downtown area.
The first-floor flat offers a one-bedroom, one-bathroom layout sleeping two guests, boasting a full galley kitchen, separate dining area, and garden access with parking; nearby attractions include beaches, restaurants, and golf courses.

This historic Dutch Colonial house is located in the heart of Greenport's historic district, just a short walk from the town's restaurants, shops, and transport links, including the bus, train, and ferry terminal. Beaches on both Long Island Sound and the bay are less than 1.6 kilometres away. The property has excellent user, location and cleanliness ratings.
The house offers five bedrooms and two bathrooms, comfortably accommodating up to eight guests. The well-equipped kitchen, multiple outdoor spaces, and family-friendly amenities make this a perfect choice for a relaxing getaway.

This three-bedroom, three-bathroom waterside residence on Shelter Island offers direct access to Menantic Creek and boasts stunning water views from almost every room, complete with a private dock and a beach area with provided water sports equipment. This property for six guests includes a fully-fenced garden, a private dipping pool, a cedar sauna, a SoloStove firepit, and is equipped with air conditioning, Wi-Fi, and on-site parking, making it ideal for those seeking a relaxing getaway.

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 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 one-bedroom flat is situated in a Victorian house in Greenport, just a short walk from the village's restaurants, wineries, and beaches.
The apartment features a private entrance, a porch, a brick patio, a spacious bedroom with an en suite bathroom, a cosy den with a queen-size pull-out sofa bed, a sunny sitting room, a fully equipped kitchen, a washer and dryer, high-speed internet, and a new flat-screen TV.