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Greenport, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Greenport, NY

Best Greenport, NY vacation rentals with a balcony

Cozy Shelter Island Cottage, Walk To Beaches And Mashomack Preserve - Greenport, NY
9.8 30 reviews

Cozy Shelter Island Cottage, Walk To Beaches And Mashomack Preserve

apartment, Shelter Island
This Shelter Island vacation home is conveniently located near the Shelter Island Ferry, offering easy access to Sag Harbor and the Hamptons, and is also close to the Mashomack Preserve.
This 1,500-square-foot house features three bedrooms, two bathrooms, and accommodates six guests, boasting a private pool, dock with beach access, gourmet kitchen, and on-site amenities including paddleboards and bikes.
Relax At A Private Beach! Three Bedrooms Await You Near Shelter Island Beaches! - Greenport, NY
No reviews

Relax At A Private Beach! Three Bedrooms Await You Near Shelter Island Beaches!

apartment, Shelter Island Heights
This Shelter Island Heights vacation home is located near Crescent Beach and Wades Beach, a short drive from Shelter Island Heights' attractions.
This 2400-square-foot house features three bedrooms, three bathrooms, and can accommodate up to ten guests, offering a fully equipped kitchen, multiple decks, a private beach access, a finished basement, and a spa.
North Fork Resort - Greenport, NY
9.6 1 review

North Fork Resort

resort, Greenport
Resort with an excellent rating of 96% based on 1 reviews. You will be based in Greenport.
Services and facilities include a swimming pool, a fridge and a barbecue. Take advantage of the garden in this resort!
Spacious 5 Bedroom Family Beach Getaway In Charming East Marion/greenport - Greenport, NY
10 4 reviews

Spacious 5 Bedroom Family Beach Getaway In Charming East Marion/greenport

apartment, East Marion
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.

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.

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.
Charming Greenport Village Farmhouse - Greenport, NY
10 14 reviews

Charming Greenport Village Farmhouse

apartment, Greenport
This Greenport Village farmhouse, situated on 0.37 acres less than half a mile from shops and restaurants, provides easy access to beaches and wineries.
The 1822 farmhouse, boasting four ensuite bedrooms and four bathrooms, comfortably accommodates four guests and features a high-end kitchen with Williams Sonoma and KitchenAid appliances, a Peloton bike, and access to five cruiser bikes and kayaks.
Delightful Cape House In Greenport - Greenport, NY
10 29 reviews

Delightful Cape House In Greenport

apartment, Greenport
This Greenport Cape Cod-style home is centrally located, within walking distance of Greenport's beach, shops, restaurants, the Hampton Jitney bus service, the Long Island Rail Road (LIRR), and the ferry.
This four-bedroom, two-bathroom house sleeps six, features a heated saltwater pool, hot tub, outdoor shower, fire pit, grill, in-house washer/dryer, and a kitchen with a fridge, freezer, and dishwasher.
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 Saltbox | North Fork Wine Retreat - Greenport, NY
9.6 37 reviews

Greenport Saltbox | North Fork Wine Retreat

apartment, Greenport
This impeccably restored historic Saltbox house in Greenport Village is minutes from 67 Steps Beach and Kontokosta Winery, and walking distance from Greenport's main attractions.
This two-bedroom, two-bathroom home sleeps six, features updated kitchen and bathrooms with a dishwasher, in-house Jacuzzi, private backyard, and provides a Prius/smart car charger; small pet fee applies.
2 Br Townhouse 1000ft From Bay Access! - Greenport, NY
9.3 6 reviews

2 Br Townhouse 1000ft From Bay Access!

house, East Marion
This house in East Marion offers a secluded retreat on Long Island's North Fork, situated a short walk from a private sandy beach and a brief drive to wineries, lavender fields, farm stands, and Greenport Village.
This 2-bedroom, 1-bathroom cottage accommodates up to 4 guests and features a full kitchen, air conditioning, internet, parking, and a spacious private backyard, making it ideal for romantic weekends or family getaways.
Greenport Village Relaxation - Greenport, NY
9.7 91 reviews

Greenport Village Relaxation

apartment, Greenport
This Greenport Village rental is a two-bedroom, one-bathroom cottage located in the Historic District, a 10-minute walk from the village center and 12 minutes from the train and Jitney stops.
The 2-bedroom home offers a backyard grill, sleeps four, includes a fridge, microwave, and dishwasher, and is near Alice's Fish Market, Barba Bianca, and Kontokosta Winery.
Beautiful Condo On Long Islands Northfork - Greenport, NY
9.7 154 reviews

Beautiful Condo On Long Islands Northfork

apartment, Greenport
This Greenport apartment is located on Long Island Sound, within walking distance of the town's restaurants, bars, and shops. It has received excellent ratings for user experience, location, and cleanliness.
This two-bedroom, two-bathroom apartment comfortably sleeps six guests. It features a kitchen with a fridge, microwave, and dishwasher, as well as a private terrace or balcony, a garden, and access to a swimming pool, clubhouse, and beach lounge chairs.

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.

Shelter Island Cottage - Greenport, NY
10 100 reviews

Shelter Island Cottage

apartment, Shelter Island
This charming cottage is located on Shelter Island, just a short walk from two beaches and close to the South Ferry. The property has received excellent ratings for its location, cleanliness, and overall experience.
The home has five bedrooms and a pool house, making it ideal for large groups or multiple families. You’ll enjoy a heated saltwater pool, a fire pit, a tennis court, and a garden, as well as access to bikes for exploring the island.
Charming North Fork Escape By The Beach - Greenport, NY
10 13 reviews

Charming North Fork Escape By The Beach

apartment, East Marion
This East Marion rental is a short walk from a pristine Long Island Sound beach and 10 minutes from Greenport Village's shops and restaurants.
The three-bedroom, two-bathroom apartment sleeps six, features a private pool, lush garden, finished basement with workspace, fully equipped kitchen including a dishwasher, air fryer, and espresso machine, and is close to North Fork vineyards and Orient's attractions.
Waterfront Greenport Condo - Greenport, NY
10 69 reviews

Waterfront Greenport Condo

apartment, Greenport
This Cliffside Resort condo in Greenport, Long Island offers stunning Long Island Sound views and private beach access.
The two-bedroom, two-bathroom unit sleeps six and includes a kitchen with a fridge and dishwasher, air conditioning, parking, and access to a heated resort pool; resort amenities include a lawn perfect for picnics and barbecues.
Greenport Getaway At Cliffside Condos - Greenport, NY
9.8 33 reviews

Greenport Getaway At Cliffside Condos

apartment, Greenport
This cliffside condo in Greenport offers direct access to a private beach and is located within 1 mile of Greenport's shops, restaurants, and vineyards.
This 2-bedroom, 2-bathroom condo accommodates up to 6 guests with a queen bed, two twin beds, and a pullout sofa, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a seasonal swimming pool, garden, and BBQ facilities.

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.

Dream Get Away - Greenport, NY
9.9 293 reviews

Dream Get Away

apartment, Greenport
Greenport Condo With Stunning Views & Beach Access - Greenport, NY
9.9 34 reviews

Greenport Condo With Stunning Views & Beach Access

apartment, Greenport
Luxury By The Sea!! - Greenport, NY
9.9 57 reviews

Luxury By The Sea!!

apartment, Southold
5br/3ba: Shelter Island, Waterview, Close To Beach - Greenport, NY
9.5 21 reviews

5br/3ba: Shelter Island, Waterview, Close To Beach

apartment, Shelter Island Heights

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.

3 Min Walk To Beach| 1 Mile To Town | Fam-friendly - Greenport, NY
10 72 reviews

3 Min Walk To Beach| 1 Mile To Town | Fam-friendly

apartment, Greenport

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.

Steps From The Water! Southold Northfork Retreat - Greenport, NY
9.9 32 reviews

Steps From The Water! Southold Northfork Retreat

apartment, Southold
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