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Best Vacation rentals and Airbnb offers in Greenport, NY
9.8 41 reviews
Greenport, NY
07/07 – 07/14
$504/nighttotal: $3528 (7 )
Waterfront Nofo Cottage W/ Public Beach Access
1 2
apartment , East Marion
This East Marion cottage boasts a direct waterfront location on Marion Lake, a 400-foot stroll from the bay beach, and a short drive from Greenport Village and the Orient Point Ferry. The two-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen with dishwasher, air conditioning, a private deck overlooking Marion Lake, and offers stunning wildlife viewing opportunities.
Greenport, NY
07/01 – 07/02
$551/nightfor 1 night
Modern Condo Retreat | A103
2 2
apartment , Greenport
This 2-bedroom, 2-bathroom condo in Greenport offers easy access to nearby beaches and dining establishments, with local attractions just a short distance away. This coastal retreat accommodates up to 6 guests and features a fully equipped kitchenette, air conditioning, a swimming pool, and a private covered patio for relaxed outdoor enjoyment.
9.1 249 reviews
Greenport, NY
07/01 – 07/02
$299/nightfor 1 night
The Cliffside Resort Condominiums
1 2
apartment , Greenport
This Greenport apartment is located just a short drive from downtown Greenport and the Hortons Point Lighthouse, offering easy access to the area's attractions. The apartment is highly rated for its cleanliness, location, and overall experience. The two-bedroom apartment spans 550 square feet and provides a comfortable space for your stay. Guests can enjoy amenities like a swimming pool, a private beach, and a terrace, as well as convenient features like a kitchen, air conditioning, and free Wi-Fi.
9.8 12 reviews
Greenport, NY
06/24 – 06/27
$1160/nighttotal: $3480 (3 )
The Lucky Oyster Est 1886 | 3bd/2ba, Walk To Town
1 1
apartment , Greenport
This Greenport home, steps from the town center, offers easy walking access to shops, restaurants, and the waterfront. The 1350-square-foot, two-story house sleeps eight, features three bedrooms, two bathrooms, a full kitchen with a six-burner stove and dual ovens, a private backyard with a grill, and beach equipment storage.
9.3 52 reviews
Greenport, NY
07/07 – 07/14
$273/nighttotal: $1911 (7 )
All Seasons Rental
2 2
apartment , Shelter Island
This Shelter Island country ranch is located near Mashomack Preserve, a five-minute drive from its hiking trails, beaches, and miniature golf. This two-bedroom, one-bathroom house sleeps four and features a full kitchen with dishwasher, in-unit laundry, a relaxing deck, and ample living space.
Greenport, NY
07/07 – 07/14
$1967/nighttotal: $13769 (7 )
Picture Perfect Greenport Cottage
3 2
cottage , Greenport
This charming cottage is located in Greenport, a short walk from the Railroad Museum of Long Island, the Camera Obscura, and the East End Seaport Maritime Museum, making it easy to explore the town's rich history and attractions. The peaceful neighborhood provides a tranquil escape from the hustle and bustle of city life. This cozy home features three bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy a relaxing soak in the shower/tub combo after a day of exploring the area's wineries, beaches, and charming downtown.
10 4 reviews
Greenport, NY
07/01 – 07/02
$669/nightfor 1 night
Cliffside Resort Poolside Condo A105
2 2
apartment , Greenport
This Greenport apartment is located in a resort community, just a short walk from the waterfront and a few minutes' drive from the charming downtown area. The apartment has earned excellent ratings for its cleanliness, location, and overall experience. This two-bedroom, two-bathroom unit can comfortably accommodate up to six guests. Enjoy amenities like a private balcony, a full kitchenette, a heated pool, charcoal grills, and two designated parking spots.
9.6 28 reviews
Greenport, NY
06/24 – 06/27
$447/nighttotal: $1341 (3 )
Sailor’s Cove
1 1
apartment , Greenport
This Greenport Village apartment is centrally located, within walking distance of the shops and restaurants, half a mile from the beach, and three blocks from a dock. The one-bedroom, one-bathroom unit sleeps two, features a kitchen with a fridge and freezer, air conditioning, parking, internet, and allows pets (with restrictions and a surcharge).
10 1 review
Greenport, NY
07/01 – 07/02
$343/nightfor 1 night
No Place Like Home
1 2
apartment , Southold
This serene apartment offers a tranquil escape in Southold, a destination known for its peaceful surroundings and proximity to natural beauty. This one-bedroom, one-bathroom unit accommodates up to two guests and features air conditioning and internet, providing a quiet spot for unwinding.
10 44 reviews
Greenport, NY
07/07 – 07/14
$785/nighttotal: $5495 (7 )
Relaxation In Greenport
3 2
apartment , Greenport
This newly renovated Greenport house, ideally situated two blocks from the Hampton Jitney, Long Island Rail Road, and Shelter Island Ferry, provides easy access to Main Street's restaurants and bars and is a three-minute drive from Greenport's beaches. The three-bedroom, two-bathroom home sleeps eight guests and boasts high-end appliances (Sub-Zero refrigerator, Wolf range, Bosch dishwasher), two Smart TVs (55" and 65"), central air conditioning, a fenced yard, and ample parking.
10 20 reviews
Greenport, NY
06/24 – 06/27
$950/nighttotal: $2850 (3 )
Newly Furnished Greenport Escape With Central Air
1 1
apartment , Greenport
This Greenport Village colonial house is located less than a mile from the beach and train, a 13-minute walk from downtown, and near the Shelter Island ferry. This 2,000-square-foot home features four bedrooms, 2.5 bathrooms, an outdoor shower, a chef's kitchen, a Weber gas grill, Sonos speakers, Nest thermostats, and accommodates up to eight guests with a 14-night minimum stay.
9.9 34 reviews
Greenport, NY
07/07 – 07/14
$717/nighttotal: $5019 (7 )
Beautiful 2 Bedroom, 2 Bath Greenport Village Loft
1 2
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.
Best Greenport, NY vacation rentals with a balcony
9.8 11 reviews
Greenport, NY
06/24 – 06/27
$1429/nighttotal: $4287 (3 )
Beachfront Greenport Villa
1 1
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.
9.5 30 reviews
Greenport, NY
06/24 – 06/27
$455/nighttotal: $1365 (3 )
North Fork Resort
1 1
resort , Greenport
Resort listing with an excellent rating of 95% based on 30 reviews. Your accommodation will be located in Greenport. Facilities and services: free parking, a fridge and a swimming pool. This resort is very convenient for families.
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.
9.4 10 reviews
Greenport, NY
07/07 – 07/14
$2370/nighttotal: $16590 (7 )
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
3 2
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.
10 3 reviews
Greenport, NY
07/01 – 07/02
$2030/nightfor 1 night
New Construction Greenport Pool House - 3 Blocks From Town
4 2
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.
9.8 8 reviews
Greenport, NY
06/24 – 06/27
$989/nighttotal: $2967 (3 )
Family Friendly Modern Island Home Steps To Beach!
1 1
apartment , Shelter Island Heights
This newly built Shelter Island Heights home, a short walk from Crescent Beach and steps from the Pridwin Hotel, offers a peaceful island escape. The 4-bedroom, 2.5-bathroom house sleeps eight guests and features a kitchen, air conditioning, a garden, parking, and internet access; enjoy nearby fine dining and explore the island by foot or bike.
10 9 reviews
Greenport, NY
07/07 – 07/14
$679/nighttotal: $4753 (7 )
Charming 2 Bedroom Cottage W/ Private Yard
2 2
house , Southold
This charming cottage is located just a short walk from Southold's main street, offering easy access to shops, restaurants, and transportation. The property has received excellent ratings for its cleanliness, location, and user experience. The cottage comfortably accommodates up to four adults and two children, with two bedrooms and one bathroom. Enjoy a private yard with a fire pit, BBQ area, and outdoor dining space, as well as a modern kitchen, central air conditioning, and a fitness center.
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?
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?
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?
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.
Destinations nearby
Best Greenport, NY vacation rentals with parking
Greenport, NY
07/01 – 07/02
$652/nightfor 1 night
The Chequit
1 2
island , Shelter Island Heights
The Chequit Hotel is situated in the tranquil surroundings of Shelter Island Heights, within easy reach of the Shelter Island Country Club and the historic Sylvester Manor. The hotel offers 35 cozy guestrooms with blackout drapes for privacy, as well as a range of amenities including an on-site restaurant, coffee shop, free Wi-Fi and self-parking.
Greenport, NY
07/07 – 07/14
$1223/nighttotal: $8561 (7 )
4-bedroom House On Lake In Delightful Shelter Island With Wifi, Ac On 3.2 Acres
4 2
apartment , Shelter Island
This four-bedroom Shelter Island house, located in Suffolk County, New York, offers easy access to attractions like the Havens House, Sylvester Manor, Shelter Island Whale's Tail, and the East End Seaport Maritime Museum. The 4-bedroom home features two bathrooms, a microwave, air conditioning, Wi-Fi, and sleeps up to 14 guests, providing a comfortable stay with local insider tips.
10 38 reviews
Greenport, NY
07/07 – 07/14
$1229/nighttotal: $8603 (7 )
Perfect Waterfront Family Vacation Home Next To The Best Vineyards In Ny!
3 2
apartment , Southold
This 3-bedroom, 2-bathroom beachfront cottage in Southold offers direct access to a private community beach and is located near the Railroad Museum of Long Island and East End Seaport Maritime Museum, with Croteaux Vineyards and Mattebella Vineyards also nearby. This pet-friendly rental features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, spa, and parking, with opportunities for swimming, boating, and fishing on Goose Creek.
9.8 11 reviews
Greenport, NY
07/01 – 07/02
$385/nightfor 1 night
Beechwood Cottage 1bd
1 2
apartment , Greenport
This modern cottage is located in a quiet district of Greenport, offering easy access to the village center and waterfront attractions. This apartment rental features one bedroom and one bathroom, accommodating up to four guests with a full kitchen, air conditioning, a swimming pool, garden, and grill, perfect for enjoying the Greenport atmosphere.
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.
9.8 162 reviews
Greenport, NY
06/24 – 06/27
$615/nighttotal: $1845 (3 )
Waterfront Escape | Private Beach, Pool & Views
2 1
apartment , Greenport
This Greenport waterfront condo offers an excellent stay for up to 6 guests. It is located on a bluff overlooking Long Island Sound, minutes from downtown Greenport. Reviewers rate the location, cleanliness, and the overall property as excellent. The condo has two bedrooms and two bathrooms. It features a private waterfront deck with grills and a private beach, a kitchenette, a smart TV, and a record player. Guests also have access to a shared pool, a great lawn, and a laundry room. The condo is close to Greenport's historic seaport, farms, wineries, and restaurants.
10 17 reviews
Greenport, NY
07/07 – 07/14
$1757/nighttotal: $12299 (7 )
Luxury Resort Style Pool Oasis, Walk To Beach
3 2
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.
10 16 reviews
Greenport, NY
07/01 – 07/02
$742/nightfor 1 night
Greenport Condo With Stunning Views & Beach Access
2 2
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.
9.8 194 reviews
Greenport, NY
07/01 – 07/02
$600/nightfor 1 night
Beautiful Waterview Condo On The North Fork Of Li
1 2
apartment , Greenport
This Greenport apartment is located at The Cliffside Resort Condominiums, just minutes from the town center and the ferry to Shelter Island. The apartment has received excellent ratings for its location, cleanliness, and overall experience. The two-bedroom, two-bathroom apartment comfortably sleeps six guests. It features a kitchen with a dishwasher, a private beach, a swimming pool, and BBQ grills.
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.
9.8 264 reviews
Greenport, NY
07/01 – 07/02
$685/nightfor 1 night
Sound Front Condominium
1 2
apartment , Greenport
Greenport, NY
07/07 – 07/14
$726/nighttotal: $5082 (7 )
Creekside House
Shelter Island
4 2
apartment , Shelter Island Heights
9.9 89 reviews
Greenport, NY
06/24 – 06/27
$1401/nighttotal: $4203 (3 )
Beachfront Greenport Villa
1 1
apartment , Southold
10 1 review
Greenport, NY
06/24 – 06/27
$1406/nighttotal: $4218 (3 )
Beachfront Greenport Villa
3 1
house , 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.
10 2 reviews
Greenport, NY
07/07 – 07/14
$1783/nighttotal: $12481 (7 )
Modern On 9th
1 2
house , 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.
