Compare best Airbnb in Greenport, NY from 100+ providers!

221 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Greenport, NY vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Greenport, NY

Best Greenport, NY vacation rentals with a balcony

Cliffside Resort Condominiums - Greenport, NY
9.0 283 reviews

Cliffside Resort Condominiums

resort, Greenport
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.
North Fork Resort - Greenport, NY
9.6 1 review

North Fork Resort

resort, Greenport
Vacation resort with an excellent rating of 96% based on 1 reviews. This accommodation is located in Greenport.
Facilities and services: a barbecue, a terrace and a garden. This is a family-friendly resort!
Stunning Sag Harbor Estate On Over 3 Acres, Pool, Tennis, Perfect For Families - Greenport, NY
No reviews

Stunning Sag Harbor Estate On Over 3 Acres, Pool, Tennis, Perfect For Families

apartment, North Haven
This Sag Harbor vacation rental is located a 12-minute walk from The Hamptons Beaches and a 4-minute drive from Sag Harbor Marine Park.
This 5-bedroom, 6-bathroom house accommodates up to 10 guests and features a heated swimming pool, hot tub, private balcony, billiards, a full kitchen with an oven and microwave, and in-unit laundry.
Beachfront Greenport Villa - Greenport, NY
9.8 13 reviews

Beachfront Greenport Villa

apartment, Southold
This beachfront home is located in Greenport, directly on the Long Island Sound, within walking distance of restaurants and bars in the Soundview area and a short bike ride from North Fork wineries, breweries, farms, and the town center. This 3-bedroom, 3-bathroom house can accommodate up to 8 guests and offers amenities such as a fully equipped kitchen, air conditioning, a garden, a spa, and parking for 3 cars.

Browse Family-Friendly Vacation Rentals in Greenport, NY

Perfect for family trips, these spacious Greenport, NY rentals and Airbnbs provide easy access to local beaches.

Gorgeous 5 Bdrm Home With Beautiful Bay Views In The Heart Of Greenport Village - Greenport, NY
10 22 reviews

Gorgeous 5 Bdrm Home With Beautiful Bay Views In The Heart Of Greenport Village

apartment, Greenport
This Greenport vacation home is conveniently located within walking distance of the Greenport Farmers' Market, Camera Obscura, and East End Seaport Maritime Museum, making it ideal for exploring the town's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The house offers 4 bedrooms, accommodating up to 10 guests, making it perfect for families or groups. Enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, a private garden, and a spa, perfect for relaxing after a day of exploring.
Year Round Family Home On Shelter Island With Indoor Heated Pool And Dock. - Greenport, NY
10 3 reviews

Year Round Family Home On Shelter Island With Indoor Heated Pool And Dock.

apartment, Shelter Island Heights
This apartment is located in the Silver Beach district of Shelter Island Heights, a 10-minute walk from Shell Beach and an 8-minute drive from Sunset Beach.
This vacation home offers 5 bedrooms, 3 bathrooms, and can accommodate up to 11 guests, featuring a private swimming pool, barbecue facilities, Wi-Fi, air conditioning, and a fully equipped kitchen with a microwave and dishwasher.
Beautiful 2 Bedroom, 2 Bath Greenport Village Loft - Greenport, NY
9.9 39 reviews

Beautiful 2 Bedroom, 2 Bath Greenport Village Loft

apartment, Greenport
This Greenport apartment is a short 5-minute walk from Front Street, Main Street shops, restaurants, and bars, and directly across from a park and playground, making it a convenient and family-friendly location. It has excellent user, location, and cleanliness ratings.
The apartment has two bedrooms and two bathrooms, accommodating up to five guests. Amenities include a kitchen with a fridge, freezer, microwave oven, and dishwasher, plus air conditioning, a garden, parking, internet, and an EV charging outlet.
Northfork Townhouse Walk To All - Greenport, NY
10 7 reviews

Northfork Townhouse Walk To All

apartment, Greenport
This 3-bedroom house is conveniently located in central Greenport, within a 10-minute walk of the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura. The home comfortably accommodates 6 guests and offers a fully equipped kitchen, outdoor barbecue grills, a garden, and free WiFi.

Frequently Asked Questions about vacation rentals in Greenport, NY

  • What are some interesting places to visit in or near Greenport, NY?

    Greenport has a lot to offer! You can visit the historic Greenport Harbor, take a walk along the waterfront, and check out the shops and restaurants on Main Street. If you're looking for something a little more adventurous, you can take a ferry to Shelter Island or visit the Long Island Aquarium and Exhibition Center in Riverhead.
  • What are the best Airbnb and vacation rentals in Greenport, NY?

    The Sandpiper- Apt #1, The Cliffside Resort Condominiums and Amazing Greenport Village Apartment In Center are the most popular Airbnb and vacation rentals in Greenport, NY among travelers.

  • Which walking or cycling routes are the best in Greenport, NY?

    For a scenic walk, try the Greenport Harbor Trail, which runs along the waterfront. You can also bike the 10-mile Greenport to Shelter Island Ferry route, which offers stunning views of the Peconic Bay. If you're looking for a longer ride, try the 20-mile route from Greenport to Mattituck, which takes you through vineyards and farmlands.
  • What are the most popular Airbnbs in Greenport, NY?

    Among the Airbnbs in Greenport, NY, The Sandpiper- Apt #1, Amazing Greenport Village Apartment In Center and Squire Chase House are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Greenport, NY?

    Greenport is a great place to get outdoors. You can go fishing, kayaking, or paddleboarding in the harbor. You can also go hiking or biking in the nearby state parks, such as Orient Beach State Park and Flanders Nature Center & Environmental Education Center. If you're feeling adventurous, you can even try kiteboarding on the beach.
  • What are the best vacation rentals with a pool in Greenport, NY?

    The Cliffside Resort Condominiums, Greenport Beach House and Sound Front Condominium are the best vacation rentals with a pool in Greenport, NY.

  • What other towns or cities can be easily accessed from Greenport, NY?

    Greenport is a great base to explore the North Fork. You can easily get to Shelter Island by ferry, and you can drive to other towns like Mattituck, Cutchogue, and Orient Point. If you're looking for a bigger city, you can drive to Riverhead, which is about 15 miles away.
  • What are the best rentals for families and kids in Greenport, NY?

  • What amenities are commonly available in vacation rentals in Greenport, NY?

    Vacation rentals in Greenport usually have basic amenities like a kitchen, bathroom, and bedrooms. You can often find rentals with additional features, such as a backyard, deck, or hot tub. Some rentals even have access to a pool or beach.
  • What are the best rentals or Airbnbs with a jacuzzi in Greenport, NY?

  • What time of year is best to rent a vacation rental Greenport, NY?

    Greenport is a great place to visit year-round, but the best time to rent a vacation rental is during the summer months, from June to August. The weather is warm and sunny, and there are plenty of outdoor activities to enjoy. If you're looking for a more relaxed experience, you can visit in the spring or fall.
  • What are the local dishes in Greenport, NY region?

    The North Fork is known for its fresh seafood, so be sure to try some local oysters, clams, and scallops. You can also find delicious farm-to-table cuisine at many restaurants in Greenport. And don't forget to try a glass of local wine from one of the many vineyards in the area.

Popular destinations

Best Greenport, NY vacation rentals with parking

Greenport Condo With Stunning Views & Beach Access - Greenport, NY
9.9 29 reviews

Greenport Condo With Stunning Views & Beach Access

apartment, Greenport
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.
4 Bedroom Sag Harbor Home W/ Pool & Tennis Access - Greenport, NY
9.7 15 reviews

4 Bedroom Sag Harbor Home W/ Pool & Tennis Access

apartment, North Haven
This Sag Harbor residence is centrally located for easy access to Sag Harbor's attractions, offering proximity to Long Beach, Main Street, a park, and bay access.
This four-bedroom, two-bathroom dwelling accommodates up to eight guests and features two living spaces, a sunroom, an outdoor deck with seating, and a dining area for ten, with amenities including air conditioning, internet, a pool, and allowing pets.
Renovated Townhouse, Walk To All - Greenport, NY
9.9 138 reviews

Renovated Townhouse, Walk To All

house, Greenport
This Greenport townhouse is located within walking distance of the town center, beaches, parks, and a local brewery, and a short bike ride from the North Fork's wineries. The three-bedroom house features a fully renovated kitchen with a dishwasher, a private backyard with an outdoor grill, and a spacious living area with a pull-out queen bed in the den for a total guest capacity of eight.
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office) - Greenport, NY
9.8 512 reviews

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

apartment, Greenport
This Greenport apartment is located in the heart of Greenport Village, just steps away from restaurants, shops, and the ferry. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment features two bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking, making it ideal for families and groups.

Neighborhoods and points of interest in Greenport, NY

Choose the Right Vacation Rentals with a Pool in Greenport, NY

A vacation rental with a pool in Greenport, NY is the ideal way to complement your daily coastal adventures.

Waterfront Greenport Getaway - Greenport, NY
9.7 23 reviews

Waterfront Greenport Getaway

apartment, Greenport
This Greenport waterfront condo overlooks the Long Island Sound on the North Fork, offering easy access to the town's shops and restaurants.
The two-bedroom, two-bathroom unit sleeps six and includes a kitchen, air conditioning, parking, a swimming pool, and a private balcony with stunning Long Island Sound views; enjoy nearby boating and fishing.
Beachfront Heated Pool Hot Tub Orient Village - Greenport, NY
9.7 26 reviews

Beachfront Heated Pool Hot Tub Orient Village

apartment, Orient
This beachfront Orient, St. Martin home boasts direct Bug Lighthouse views and easy access to Orient Village's yacht club and restaurants.
The three-bedroom, two-bathroom house features a fully equipped kitchen, a private pool and hot tub, beach access, kayaks, paddleboards, and a 65" TV, comfortably accommodating six guests.
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home - Greenport, NY
9.6 11 reviews

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

apartment, Orient
This waterfront vacation home is located just three miles from Oysterponds Historical Society, Island's End Golf & Country Club, and Truman's Beach, offering easy access to local attractions and a peaceful setting. The home boasts excellent user ratings, making it a popular choice for travelers.
The vacation rental features three bedrooms and two bathrooms, comfortably accommodating up to six guests. The house offers a range of amenities, including a fully equipped kitchen, a swimming pool, a tennis court, and a spacious garden, perfect for enjoying the beautiful Orient outdoors.
New Construction Greenport Pool House - 3 Blocks From Town - Greenport, NY
10 4 reviews

New Construction Greenport Pool House - 3 Blocks From Town

house, Greenport
This Greenport villa is 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 known for its charming shops, restaurants, and waterfront views.
This 2,700 square foot home has three bathrooms, providing ample space for families or groups. Enjoy a private pool, spa tub, outdoor patio, and a fully equipped kitchen with modern amenities, including free WiFi.

Browse Waterfront Vacation Rentals in Greenport, NY

Enjoy a relaxing beach getaway with these coastal and seaside vacation rentals in Greenport, NY. Book your next shoreside stay today.

Beautiful Condo On Long Islands Northfork - Greenport, NY
9.7 149 reviews

Beautiful Condo On Long Islands Northfork

apartment, Greenport
Bayview House With Salt Water Pool & Private Chef - Greenport, NY
9.8 16 reviews

Bayview House With Salt Water Pool & Private Chef

apartment, Greenport
The Cliffside Resort Condominiums - Greenport, NY
9.2 234 reviews

The Cliffside Resort Condominiums

apartment, Greenport
Beachfront Greenport Villa - Greenport, NY
9.9 98 reviews

Beachfront Greenport Villa

apartment, Southold

Traveler-Approved Luxury Vacation Rentals in Greenport, NY

Indulge in a luxury vacation rental in Greenport, NY, where high-end design meets world-class 5-star comfort.

Luxury North Fork Estate Pool, Spa And Vineyard - Greenport, NY
10 7 reviews

Luxury North Fork Estate Pool, Spa And Vineyard

apartment, Southold

Explore Vacation Rentals with Saunas in Greenport, NY

Maximize your recovery with an on-site sauna, a standard feature at these premier Greenport, NY vacation rentals.

Perfect House:location! Location! Location! - Greenport, NY
10 4 reviews

Perfect House:location! Location! Location!

apartment, Greenport
Menantic House | Waterfront, Private Dock & Pool - Greenport, NY
No reviews

Menantic House | Waterfront, Private Dock & Pool

apartment, Shelter Island
©2026 cozycozy.com