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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

Waterfront House With Dock And Private Beach - Greenport, NY
10 25 reviews

Waterfront House With Dock And Private Beach

apartment, Shelter Island
This waterfront vacation home offers stunning views and proximity to major tourist attractions within a 2-mile radius, including Wades Beach, The Hamptons Beaches, Havens House, Shelter Island Historical Society, and Mashomack Preserve. It boasts an excellent user rating.
The 1,600-square-foot house has 3 bedrooms, 3 bathrooms, and can accommodate up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a cozy fireplace, a private garden with barbecue grills, a spacious balcony, free Wi-Fi, and parking. The house is also pet-friendly and family-friendly.
Aqua Vista - Greenport, NY
9.9 760 reviews

Aqua Vista

apartment, Greenport
This Greenport apartment is located in the center of Greenport Village, just steps away from restaurants, shops, and the Shelter Island Ferry. It has excellent user, location, and cleanliness ratings. This two-bedroom rental comfortably sleeps six guests. It features a fully equipped kitchen, a private balcony, and a garden.
The apartment is air-conditioned, has free internet access, and allows pets, making it a perfect choice for families and groups.
Waterfront Condo C-204 At The Cliffside Resort - Greenport, NY
9.9 199 reviews

Waterfront Condo C-204 At The Cliffside Resort

apartment, Greenport
Water's Edge luxury suite is located in the Captain's Roost Building of The Cliffside Resort Condominiums in Greenport, New York, on the North Fork of Long Island, with panoramic waterfront views from the master bedroom, living room, and private covered deck. Rated excellent by users for its location, cleanliness, and amenities, this two-bedroom, two-bathroom apartment accommodates up to 6 guests in 700 square feet.
The apartment features a fully equipped kitchenette with a dishwasher, air conditioning, a DVD player, a folding laptop table, a sturdy step ladder, a small vacuum, and cleaning supplies. Guests have access to a seasonal pool and coin-operated washer and dryer in the basement, as well as a private beach just yards away.
Bright And Spacious Summer Home Steps From The Beach - Greenport, NY
9.0 44 reviews

Bright And Spacious Summer Home Steps From The Beach

apartment, Shelter Island Heights
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.

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.

Cozy Farmhouse Retreat In North Fork, Ny - Greenport, NY
9.8 133 reviews

Cozy Farmhouse Retreat In North Fork, Ny

apartment, Greenport
Arthur's Vineyard, a 1905 farmhouse in Greenport, is a 10-minute walk from Greenport village's beaches, marina, restaurants, boutiques, and the Long Island Rail Road train station. This three-bedroom, two-bathroom house sleeps six and offers keyless entry, a modern kitchen with dishwasher, central air conditioning, a landscaped backyard, and amenities for families with young children (crib, booster seat, stair gates available upon request).
Quiet 3br Home In East Marion. Private Beach Access 3 Min Walk Away. - Greenport, NY
9.6 5 reviews

Quiet 3br Home In East Marion. Private Beach Access 3 Min Walk Away.

apartment, East Marion
This East Marion vacation home, located within 3 miles of Island's End Golf and Country Club, Truman's Beach, and Kontokosta Winery, offers easy access to local attractions. This three-bedroom, two-bathroom house sleeps six, boasts a private pool, free WiFi, and a fully equipped kitchen including a refrigerator, microwave, and dishwasher, plus outdoor amenities like a patio and garden.
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.
The Greenport Beach Cottage: 3 Min Walk To Beach, 1 Mile To Town - Greenport, NY
10 1 review

The Greenport Beach Cottage: 3 Min Walk To Beach, 1 Mile To Town

cottage, Greenport
This Greenport beach house is a three-minute walk from a lifeguarded beach with restrooms and one mile from Greenport village, offering easy access to the Greenport Carousel and Sylvester Manor.
This 750-square-foot vacation rental sleeps five, featuring two bedrooms, one bathroom, a fully equipped kitchen, outdoor shower, fire pits, and beach gear; three Roku TVs provide entertainment.

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

Private 1st Flr Apt W/ Patio 3 Blocks From Beach - Greenport, NY
9.8 145 reviews

Private 1st Flr Apt W/ Patio 3 Blocks From Beach

apartment, Greenport
This Greenport apartment is located in a quiet neighborhood, just blocks from the beach, train station, restaurants, and a park. It has excellent user, location, and cleanliness ratings.
This comfortable rental has one bedroom and one bathroom, accommodating up to four guests. You'll enjoy a private entrance, patio, a fully equipped kitchen, air conditioning, a garden, and parking.
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.
Superb Shelter Island 4 Bed Designer With A Pool - Greenport, NY
10 7 reviews

Superb Shelter Island 4 Bed Designer With A Pool

house, Shelter Island Heights
This Shelter Island Heights home is located on a quiet street, just a short walk from Sunset, Silver, and Shell beaches, making it ideal for enjoying the island's natural beauty. The property has consistently received excellent ratings for user experience, location, and cleanliness.
The house offers four bedrooms and three bathrooms, comfortably accommodating up to eight guests. Enjoy a heated saltwater pool, a hot tub, a fully stocked kitchen, and a wrap-around porch, two large decks, and an open floor plan.
Suite 5:  2 Bedroom, 1 Bath - Greenport, NY
9.1 18 reviews

Suite 5: 2 Bedroom, 1 Bath

apartment, Orient
This two-bedroom suite in Orient, New York, offers easy access to Sound Beach, a short walk from the Orient Country Store and across from a local candy store.
The apartment features a fully equipped kitchen, one bathroom with a shower/tub combination, room air conditioning units, and accommodates up to four guests.

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 Escape | Private Beach, Pool & Views - Greenport, NY
9.7 175 reviews

Waterfront Escape | Private Beach, Pool & Views

apartment, Greenport
This waterfront condo is located just minutes from the bustling center of Greenport village, offering easy access to shops, restaurants, and historic landmarks. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The two-bedroom, two-bathroom unit comfortably accommodates six guests. Enjoy the private waterfront deck, private beach access, shared pool, and communal yard, along with a well-equipped kitchen, comfortable living space, and a king-sized bed in the master suite.
North Fork Resort - Greenport, NY
9.6 1 review

North Fork Resort

resort, Greenport
Resort listing with an excellent rating of 96% based on 1 reviews. You will be based in Greenport.
Facilities and services include a terrace, free parking and a fridge. Take advantage of the garden in this resort in Greenport.
Paradise Found - Walk To Private Beach & In-ground Pool! - Greenport, NY
9.6 9 reviews

Paradise Found - Walk To Private Beach & In-ground Pool!

apartment, Southold
This Southold vacation home, perfect for families, sits conveniently near Croteaux Vineyards, Corey Creek Winery, and Osprey's Dominion (within 3 miles), and is also within 6 miles of Horton Lane Beach and Goldsmith's Inlet Park.
This 3-bedroom, 2-bathroom house sleeps 9, boasts a fully equipped kitchen, laundry facilities, a swimming pool, patio, gas grills, fireplace, Smart TV, and accommodates pets.
4br/3.5ba: Southold, Fire Pit, Close To Town/beach - Greenport, NY
9.9 24 reviews

4br/3.5ba: Southold, Fire Pit, Close To Town/beach

house, Southold
This Southold vacation home is located just 0.3 miles from The Old Field Vineyards and within a 3-mile radius of Sparkling Pointe and Mattebella Vineyards, making it an ideal choice for wine enthusiasts. The property has received excellent ratings for location, cleanliness, and overall user experience.
This 3,500 square foot home comfortably accommodates up to 10 guests. Enjoy a fully equipped kitchen, a washing machine, 4 bathrooms, a fireplace, a balcony, a barbecue grill, and a Smart TV for entertainment.

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
Gull Pond Getaway - Greenport, NY
8.0 1 review

Gull Pond Getaway

apartment, Greenport
Creekside House 
Shelter Island - Greenport, NY
10 3 reviews

Creekside House Shelter Island

apartment, Shelter Island Heights
North Fork Sound Front Home With Pool - Greenport, NY
9.8 44 reviews

North Fork Sound Front Home With Pool

apartment, Greenport

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.

The Cliffside Resort Condominiums - Greenport, NY
9.2 221 reviews

The Cliffside Resort Condominiums

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.

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

Luxury By The Sea!!

apartment, Southold
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