Compare accommodations in Greenport, NY from 100+ providers!

This waterfacing residence is located in historic Deering Harbor, offering convenient access to local markets, restaurants, marinas, beaches, and ferry services.
This 8-guest capacity apartment features a chef's kitchen with a freezer and dishwasher, air conditioning, a heated swimming pool, a garden, sauna, fitness center, and 2 bathrooms, ideal for families and pet owners seeking privacy on Shelter Island.

This Greenport vacation home, located near Gull Pond, is a five-minute drive from the maritime village and beaches.
The 4-bedroom, 2-bathroom house sleeps nine, features a private hot tub, saltwater pool (opening summer 2025), air hockey, foosball, and two TV rooms, on a secluded 3.8-acre lot.

This luxurious 6,000-square-foot North Haven Shores rental, offered by Iconic Modern, is situated near Gansett Creek and Noyac Bay, minutes from Sag Harbor's Main Street and the Shelter Island Ferry.
The six-bedroom, seven-bathroom residence boasts resort-style amenities including a pool, jacuzzi, sauna, fitness center, and parking, accommodating up to twelve guests and offering easy access to local attractions and recreational activities.

This 2-bedroom condo offers a cliffside location on the Long Island Sound in Greenport, providing direct access to local wineries and farms on the North Fork.
This accommodation features air conditioning, a kitchen with a microwave and dishwasher, and parking, with a guest capacity of six, ideal for exploring the natural beauty and attractions of the North Fork.

This restored 1905 farmhouse is located in East Marion, just a 5-minute walk from the Hampton Jitney, Sep's farm stand, and Angels Market, offering easy access to local amenities and attractions. This property consistently receives excellent user ratings for location, cleanliness, and overall experience.
The 2700 square foot home features 4 bedrooms, 3 bathrooms, and can comfortably accommodate 6 guests. Enjoy a gourmet kitchen, a large fenced-in backyard with a heated pool, a back deck, BBQ, and hammock, plus internet, air conditioning, and parking.

This Southold vacation rental, steps from a private beach and across from a vineyard, offers direct access to Shelter Island via a short 5-minute ferry ride.
The 3200-square-foot home features five bedrooms sleeping ten, a modern contemporary design with high-end appliances (Sub-Zero, Wolf), abundant amenities (kayaks, bikes, beach gear, Sonos sound system), and expansive outdoor spaces including a deck, fire pit, and BBQ.

This spacious East Marion, New York home boasts five bedrooms and three-and-a-half bathrooms, offering easy access to nearby beaches and vineyards on the North Fork.
The 5-bedroom house features an extraordinary pool and garden, an outdoor kitchen with a fireplace, a designated playroom, and accommodates up to 15 guests with amenities including a dishwasher, air conditioning, and Wi-Fi.

This Shelter Island Heights home is steps from Pipes Cove's private beach and boat launch, minutes from Greenport and Southold villages.
The four-bedroom, three-bathroom house sleeps ten guests and features a fully equipped kitchen, air conditioning, a garden, parking, Wi-Fi, and breathtaking Peconic Bay and Shelter Island views.

This East Marion condo offers a 7-minute walk to Island's End Golf and Country Club and is a 2-minute drive from Kontokosta Winery.
This 4-bedroom, 3-bathroom vacation rental accommodates up to 10 guests, featuring a full kitchen with microwave and dishwasher, air conditioning, Wi-Fi, and on-site parking.

This Greenport apartment is conveniently located just a mile from the ferry, making it easy to explore the North Fork and beyond, and it's also a short drive from the popular Splish Splash water park. This rental has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers 900 square feet of space, with two bedrooms and one bathroom, comfortably accommodating up to six guests. You'll enjoy a fully equipped kitchen, air conditioning, free Wi-Fi, a terrace or balcony, and a garden, perfect for relaxing and enjoying the Greenport atmosphere.

Cliffside Resort Condominiums offers beachfront apart-hotel accommodations in Greenport, New York, situated within 3.1 miles of Kontokosta Winery, 67 Steps Beach, and Norman E. Klipp Marine Park.
This resort provides apartments with complimentary WiFi, air conditioning, a basic kitchen, two bathrooms, a seating area, and furnished balconies, along with on-site amenities including a swimming pool, garden, and parking, and allows pets.

This East Marion rental, offering panoramic Peconic Bay views, is situated less than 2 miles from historic Greenport and provides exclusive access to Truman Beach.
This 3-bedroom, 3-bathroom house accommodates up to 6 guests and features a wrap-around deck with BBQ, a full laundry room, beach amenities, and driveway parking.

This colonial-style vacation home is located in Greenport, a charming maritime town on the North Fork of Long Island, within easy reach of beaches, wineries, and local landmarks. It's highly rated by previous guests, receiving excellent reviews for its comfort and amenities.
This 5-bedroom, 4-bathroom house spans 3200 square feet and comfortably accommodates up to 10 guests. Enjoy features like a fully equipped kitchen, a Jacuzzi, a garden, and parking, as well as access to water activities, making it perfect for families and groups seeking a relaxing getaway.

This 6-bedroom home is situated on a private 6-acre property in Southold, offering waterfront views and easy access to four beaches within a 2-4 minute drive. The property has received excellent ratings for location, cleanliness, and overall user experience.
This spacious vacation rental comfortably accommodates up to 14 guests and features a modern design with a large eat-in kitchen, a separate kids' space, a full chef's outdoor kitchen, a heated saltwater pool, a hot tub, a sauna, a gym, and a private dock. Guests can enjoy a variety of activities, including swimming, fishing, crabbing, kayaking, paddle boarding, and biking.

This 3-bedroom, 2-bathroom home is located in Greenport, within walking distance of the town's best restaurants, bars, and shops. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The spacious home comfortably accommodates up to 9 guests and features a screened-in patio, a hot tub, a grill, and a fully equipped kitchen. Enjoy the private yard, strong Wi-Fi, and take advantage of special offers for longer stays.

This beach house is located in Hay Beach, a neighborhood on Shelter Island, a short distance from Menhadden Lane Beach and Mashomack Preserve. It has received excellent user ratings, making it a popular choice for travelers. This 4,080 square foot home comfortably accommodates 10 guests in its four bedrooms and three bathrooms. The house features amenities like a private beach, a dock, a grill, and modern technology for entertainment, along with a garden, a terrace, and a jacuzzi.