Greenport Vacation Rentals

Our Favorite Vacation Rentals in Greenport

  • Victorian Seasons 5-bedroom Manor
     Country House
    Booking.com
    From
    $1,250
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,574
  • Victorian Seasons Cape
     Country House
    Booking.com
    From
    $650
  • Relaxed Village Farmhouse
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $702
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $448
  • The Farm on the North Fork
     Country House
    Booking.com
    From
    $253
  • East Hampton Classic
    Excellent4br Home/Apartment
    Flipkey
    From
    $1,136

Check prices for these upcoming dates

Greenport Vacation Rentals with a Pool

  • Waterfront Condo C-204 at The Cliffside Resort
    Excellent2br Home/Apartment
    Airbnb
    From
    $565
  • Modern, spacious SI home with heated gunite pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $706
  • Chic Shelter Island Home, Pool and Gardens
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,040
  • NOFO Escape
     6br Home/Apartment
    Airbnb
    From
    $1,099

Greenport Vacation Rentals with Wi-Fi

  • Walk to it all! - Eat, Drink, Beach, Shop - Apt #1
    Excellent2br Home/Apartment
    Airbnb
    From
    $325
  • Beautiful Cottage Home W/ Private Beach Access
    Excellent3br Home/Apartment
    Airbnb
    From
    $424
  • House on First
    Excellent2br Home/Apartment
    Airbnb
    From
    $271
  • Shelter Island get away
    Excellent3br Home/Apartment
    Airbnb
    From
    $698

Greenport Pet-Friendly Vacation Rentals

  • Sag Harbor Perfect For Extended Family and Friends
     5br Home/Apartment
    HolidayLettings
    From
    $3,075
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $3,026
  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $2,221

Greenport Travel Guide

Greenport is a small village of 2,230 people in Long Island, New York. Despite its small size, it’s the perfect place for groups of family and friends to spend a vacation as it offers a number of beautiful parks, fine restaurants, and shopping malls.

Things to Do in Greenport

Greenport’s guests can spend the day sun tanning and swimming at Fifth Street Beach and Park, before following up with a BBQ and an hour or two on the park’s various playgrounds. They can also book a session with East End Charters and spend the afternoon exploring the Greenport area by sea or make their way to Mitchell Park where they can experience the magic of the Camera Obscura, ride the antique carousel, or go skating during the winter months. Guests who enjoy learning can educate themselves on the history of the area at the Railroad Museum of Long Island, the East End Seaport Maritime Museum, and the Fireboat Firefighter Museum which offers demonstrations, tours, and stories. Guests of legal age can spend their spare time sampling the village’s local beers at the Greenport Harbor Brewing Co, while are lovers can admire the unique artworks showcased at the Nova Constellatio Gallery.

Best Places to Stay in Greenport

The available rentals in Greenport are perfect for hosting get togethers and spending quality time with your loved ones. Spacious and decorated with modern decor, they are comforting and warm. Guests can rent a vacation house, a hotel room, or a single room in someone’s home, offering variety to meet every traveler’s budget.

Best Time to Visit Greenport

The best time to visit is during the month of September. During this month, the weather is still warm and welcoming, but accommodation prices have dropped.

Best Events in Greenport

Greenport is known for its events. Many of the village’s residents attend events in both Greenport and the surrounding cities. A few of these fun events include the Maritime Festival, the Parade of Lights and Tree Lighting, the Halloween Costume Skate, the Fall Folk Festival, and the North Folk TV Festival. Although all of these events are well loved, the Maritime Festival is a particular favorite offering a parade, kayak and boat races, water sport demonstrations, model ship building and wood carving, food, artisan vendors, children’s activities, local beers, movie screenings, and live entertainment.

Things to Do for Families in Greenport

Families in Greenport can spend a weekend browsing the village’s various shops and boutiques, a few of the best being Creations By Lisa, Impulse Boutique, and Island’s End Woodcraft. They can take a short trip to Riverhead to burn excess energy at Safari Adventure, which features a calming spa, a sensory area, a 3 & under area, slides, an inflatable obstacle course and disco dome bouncer, and a playground.

Price and Availability in Greenport

Most expensive
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The cheapest day to stay at a vacation rental in Greenport tends to be Wednesday, while the most expensive day tends to be Friday. Vacation homes in Greenport tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Greenport is in August, while the cheapest month is in October. The most popular time to book a vacation rental in Greenport is in the high season in August. Greenport has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Greenport

Rainy days
70° 10°
4
63° 18°
2
59° -2°
2
68°
3
63° 19°
3
75° 27°
2
90° 41°
1
90° 48°
1
99° 55°
1
95° 55°
2
91° 48°
4
81° 32°
2
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Greenport. The warmest months in Greenport are June and May, when temperatures reach 99 ˚F. The coolest month is December, when temperatures drop to -2 ˚F. The wettest month in Greenport is April with 4.07 inches of rain, while the driest month is July with 0.74 inches of rain.

What Expert Travelers Think

  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

    Kaelin
    KaelinKindly Kae
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School

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