Holiday Rentals in Greenport, NY

This unique Greenport property, a converted 1867 church, is centrally located within easy walking distance of Greenport's restaurants, shops, beach, the Long Island Rail Road (LIRR) station, and the Jitney bus stop.
The self-catering property offers one bedroom, one bathroom, sleeping up to two guests, and boasts a modern kitchen with appliances including a dishwasher and microwave, a comfortable living room with a fireplace and 65" television, plus included two-hour electric bike rental.

This holiday home is situated on a peaceful street in Shelter Island Heights, just a short stroll from Sunset, Silver, and Shell beaches. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has a spacious layout that can accommodate up to eight guests. It features a range of amenities including a heated saltwater pool, a hot tub, a fully equipped kitchen, and three dedicated workspaces.

This apartment is situated in the heart of Greenport Village, just a short walk from the restaurants, bars, shops, coffee shops, the Shelter Island Ferry, the Long Island Railroad (LIRR), and the Hampton Jitney. It has received excellent ratings for location, cleanliness, and user experience.
The property is a two-bedroom, one-bathroom dwelling that can comfortably accommodate up to six guests. This family-friendly apartment offers a range of amenities including a kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and parking.

This Shelter Island holiday home, located near beaches and a 1.4km walk from Whale's Tail Park and a 2.1km walk from Havens House, offers convenient on-site parking.
The three-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, a private terrace, swimming pool, garden, Wi-Fi, and in-unit laundry facilities, comfortably sleeping up to six guests.

This restored 1850s farmhouse is situated in East Marion, a short bike ride from a private beach and Lavender by the Bay, and a 5-minute drive (8km) from Greenport. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The farmhouse has 4 bedrooms and 3 bathrooms, comfortably sleeping up to 10 guests. It features a well-equipped kitchen, a spacious patio with a pergola, a covered wraparound porch, an outdoor shower, a BBQ, and a hammock, perfect for relaxing and enjoying the outdoors.

This Southold apartment, sleeping seven guests, is within walking distance of Southold Beach and 4.8km from Greenport Village, offering easy access to local vineyards.
The two-bedroom, two-bathroom flat features a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, parking, and boasts three bedrooms with twin, queen, and pull-out queen beds; enjoy water views and a peaceful atmosphere.

Apartment for up to 8 guests with an excellent rating of 98% based on 99 reviews. You will be located in East Marion.
Facilities and services: free parking, a washing machine and an iron. This is a pet-friendly apartment!

This Greenport Village apartment, a 1930s cottage in the Historic District, is a 1.6km walk from Greenport's train and Jitney stops and within walking distance of restaurants such as Barba Bianca and Frisky Oyster.
The two-bedroom, one-bathroom property sleeps four, features a kitchen with fridge, microwave, and dishwasher, plus a garden, parking, and air conditioning; nearby activities include Kontokosta Winery and Alice's Fish Market.

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 two-bedroom apartment is situated on Long Island Sound in Greenport, a short distance from the town centre and local wineries, offering a peaceful and scenic setting. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This self-catering accommodation comfortably sleeps up to six guests and features a spacious living room with a sofa bed, two private bathrooms, and a fully equipped kitchen. Guests can enjoy access to a range of amenities, including a heated swimming pool, a clubhouse, barbecue facilities, and a garden, as well as activities such as morning yoga and outdoor movie screenings.

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.