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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

Pool/5 Min Walk To Beach/restaurants/museums- Village House W/backyard - Greenport, NY
10 20 reviews

Pool/5 Min Walk To Beach/restaurants/museums- Village House W/backyard

apartment, Sag Harbor
This Sag Harbor vacation rental is situated a 9-minute walk from Havens Beach and an 11-minute walk from Sag Harbor Marine Park.
This 6-bedroom, 5.5-bathroom house accommodates up to 14 guests and features a heated swimming pool, garden, Wi-Fi, and on-site parking.
Waterfront House With Dock And Private Beach - Greenport, NY
10 24 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.
Meadowood Manor By Rove Travel - 6br Outdoor Spaces - Greenport, NY
9.2 38 reviews

Meadowood Manor By Rove Travel - 6br Outdoor Spaces

house, Noyack
Meadowood Manor, a Sag Harbor house rental in Noyack, is conveniently located near Foster Memorial Beach (1.7 miles) and offers easy access to other Long Island attractions like Montauk Point Lighthouse (20-27 miles away).
This 3400-square-foot home boasts a fully equipped kitchen, private patio, swimming pool, jacuzzi, and free Wi-Fi, perfect for a relaxing Noyack getaway.
Aqua Vista - Greenport, NY
9.9 757 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.

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.

Greenport Beachfront Home | Private Beach & Sunset - Greenport, NY
No reviews

Greenport Beachfront Home | Private Beach & Sunset

apartment, Southold
This Southold beachfront rental offers direct private access to the North Fork of Long Island's tranquil waters, ideal for swimming, fishing, paddleboarding, and kayaking. This family-friendly 4-bedroom, 2-bathroom house accommodates up to 9 guests and features a full kitchen, air conditioning, a garden, fitness center, parking, an expansive dual-sided deck with a firepit and dining area, and a dedicated outdoor BBQ for enjoying unobstructed sunset views.
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.
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.
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.

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

Firefly Alley - Greenport, NY
10 3 reviews

Firefly Alley

apartment, Shelter Island
This sustainably built Shelter Island cottage, near Sylvester Manor Farmstand and Whale's Tail Mini Golf, offers stunning views of a 24-acre wooded preserve with walking trails.
The two-bedroom, one-bathroom house sleeps four, features a gourmet kitchen with Bosch appliances, a stylish bathroom with a soaking tub, and includes two Chatham beach cruiser bikes and a Tesla wall charger; eco-friendly features like solar power with battery backup are also included.
Newly Built Ranch, Beautifully Landscaped With Pool, Large Yard, Patio,... - Greenport, NY
10 27 reviews

Newly Built Ranch, Beautifully Landscaped With Pool, Large Yard, Patio,...

apartment, Greenport
This Greenport vacation home is conveniently located less than a mile from Kontokosta Winery and 67 Steps Beach, and within two miles of Stony Brook Eastern Long Island Hospital.
This 1650-square-foot house features three bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating up to six guests and offering access to a fitness center, gas grills, and a private yard.
Villa Saltwater Haven - Greenport, NY
No reviews

Villa Saltwater Haven

house, Wainscott
This 7-bedroom house is located in Wainscott, East Hampton, 11 miles from Montauk Point Lighthouse and 16 miles from Second House Museum.
This villa offers a 3000 square feet floor area with an outdoor swimming pool, garden, terrace, fireplace, and parking, accommodating up to 27 guests with a fully equipped kitchen and WiFi.
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.

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.
New Victorian Gem In Greenport - Greenport, NY
10 14 reviews

New Victorian Gem In Greenport

apartment, Greenport
This newly renovated Victorian vacation home in Greenport offers a historic stay within a short walk to the village center, providing convenient access to restaurants, shopping, and the East End Seaport Maritime Museum.
This 5-bedroom, 4-bathroom house accommodates up to 12 guests with features like a kitchen including a fridge, microwave, and dishwasher, air conditioning, a swimming pool, terrace, garden, and parking, with proximity to The Hamptons Beaches and Orient Beach State Park.
Luxury Resort Style Pool Oasis, Walk To Beach - Greenport, NY
10 20 reviews

Luxury Resort Style Pool Oasis, Walk To Beach

apartment, Shelter Island Heights
This beach house is located in Hay Beach, Shelter Island Heights, within 3 miles of Menhadden Lane Beach, Gardiner's Bay Country Club, and Shelter Island Whale's Tail. It has received excellent ratings for location, cleanliness, and overall user experience.
The home is a 3-bedroom, 2-bathroom retreat with 1500 square feet, comfortably accommodating up to 6 guests. Enjoy access to a private pool, a fenced yard, a fireplace, a spa tub, a fully equipped kitchen, free Wi-Fi, and a terrace or balcony.
Sound Front Condominium - Greenport, NY
9.8 282 reviews

Sound Front Condominium

apartment, Greenport
This Greenport apartment is located a short walk from the charming downtown area and just a few blocks from the waterfront, offering easy access to shops, restaurants, and stunning harbor views. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
The two-bedroom, two-bathroom apartment comfortably sleeps six guests and features flexible sleeping arrangements, allowing for a variety of traveler needs. Enjoy modern amenities like Wi-Fi, a fully equipped kitchen, and air conditioning, along with a private garden, swimming pool, and parking.

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.

Walk To Town, Greenport Village - Harbor Views - Greenport, NY
9.9 82 reviews

Walk To Town, Greenport Village - Harbor Views

apartment, Greenport
Beautiful Modern Home & Guest House With 8 Bedrooms Total - Greenport, NY
No reviews

Beautiful Modern Home & Guest House With 8 Bedrooms Total

apartment, Northwest Harbor
Waterfront Greenport Getaway - Greenport, NY
9.7 23 reviews

Waterfront Greenport Getaway

apartment, Greenport
Incredible 2 Bedroom Waterfront Cottage! - Greenport, NY
9.6 78 reviews

Incredible 2 Bedroom Waterfront Cottage!

resort, 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.

Victorian Pearl - Greenport, NY
10 85 reviews

Victorian Pearl

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.

Villa Nostro Palazzo - Greenport, NY
No reviews

Villa Nostro Palazzo

house, Wainscott
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