Greenport Vacation Rentals

Our Favorite Vacation Rentals in Greenport

  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Victorian Seasons Stirling
    Excellent5br Home/Apartment
    HolidayLettings
    From
    $1,574
  • The Farm on the North Fork
     Country House
    Booking.com
    From
    $305
  • Relaxed Village Farmhouse
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $702
  • Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $615
  • East Marion Home Walk to Beach-3 Mi to Greenport!
     3br Home/Apartment
    HolidayLettings
    From
    $419
  • East Hampton Classic
    Excellent4br Home/Apartment
    Flipkey
    From
    $1,840
  • Sag Harbor Perfect For Extended Family and Friends
     5br Home/Apartment
    HolidayLettings
    From
    $3,075

Check prices for these upcoming dates

Greenport Vacation Rentals with a Pool

  • 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
    $650
  • Beautiful condo on Long Islands Northfolk
    Good2br Home/Apartment
    Airbnb
    From
    $622
  • Shelter Island home with pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $593

Greenport Vacation Rentals with Wi-Fi

  • Walk to it all! - Eat, Drink, Beach, Shop - Apt #1
    Excellent2br Home/Apartment
    Airbnb
    From
    $184
  • Garden wing of 1830 Greenport home
    Excellent2br Home/Apartment
    Airbnb
    From
    $214
  • BRAND NEW Full House in Greenport
    Excellent3br Home/Apartment
    Airbnb
    From
    $622
  • Beautiful Cottage Home W/ Private Beach Access
    Excellent3br Home/Apartment
    Airbnb
    From
    $367

Greenport Pet-Friendly Vacation Rentals

  • 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
  • Luxury East Hampton Home w/Private Saltwater Pool!
     5br Home/Apartment
    HolidayLettings
    From
    $1,293
  • 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
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
59°
3
61°
2
66°
2
72° 27°
3
86° 39°
2
91° 46°
2
97° 61°
2
91° 52°
1
84° 43°
0
88° 36°
3
70° 18°
2
59° 12°
4
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Greenport. The warmest months in Greenport are June and July, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to 0 ˚F. The wettest month in Greenport is January with 4.39 inches of rain, while the driest month is April with 0.35 inches of rain.

What Expert Travelers Think

  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly

Destinations near Greenport

  • New York14,524 Properties
  • Brooklyn9,352 Properties
  • Niagara Falls3,942 Properties
  • Queens2,643 Properties
  • Lake Placid1,424 Properties
  • Montauk1,415 Properties
  • Ithaca1,381 Properties
  • Sag Harbor805 Properties
  • Rochester794 Properties
  • Amagansett764 Properties
  • Lake George Village762 Properties
  • Hampton Bays669 Properties
  • Southampton662 Properties
  • Springs645 Properties
  • Ellicottville590 Properties
  • Albany552 Properties
  • Hunter550 Properties
  • Hudson541 Properties
  • Village of East Hampton526 Properties
  • Saugerties517 Properties
  • Woodstock511 Properties
  • Windham478 Properties
  • Cooperstown475 Properties
  • Ocean Beach430 Properties
  • Canandaigua423 Properties
  • Lake George419 Properties
  • Geneva407 Properties
  • Bridgehampton394 Properties
  • Saranac Lake392 Properties
  • Beacon367 Properties
  • Kingston357 Properties
  • Penn Yan348 Properties
  • Wilmington344 Properties
  • Hammondsport337 Properties
  • Watkins Glen332 Properties
  • Noyack330 Properties
  • Cherry Grove330 Properties
  • Syracuse320 Properties
  • Staten Island319 Properties
  • Buffalo304 Properties
  • Yonkers301 Properties
  • Watermill301 Properties
  • Chestertown287 Properties
  • Alexandria Bay284 Properties
  • New Paltz278 Properties
  • East Quogue272 Properties
  • Southold262 Properties
  • Bolton Landing250 Properties
  • Long Beach245 Properties
  • Chautauqua242 Properties
  • Warrensburg240 Properties
  • Wainscott239 Properties
  • Queensbury232 Properties
  • Cortland231 Properties
  • North Creek229 Properties
  • Old Forge229 Properties
  • Binghamton221 Properties
  • Plattsburgh216 Properties
  • Shelter Island215 Properties
  • White Plains215 Properties
  • Auburn214 Properties
  • Rhinebeck211 Properties
  • Catskill211 Properties
  • Westhampton Beach202 Properties
  • Westhampton199 Properties
  • Poughkeepsie195 Properties
  • Trumansburg195 Properties
  • Pulaski194 Properties
  • Skaneateles191 Properties
  • Saratoga Springs182 Properties
  • Schroon Lake163 Properties
  • Dundee160 Properties
  • Clayton152 Properties
  • Amherst150 Properties
  • Quogue145 Properties
  • Newburgh133 Properties
  • Mount Vernon116 Properties
  • Fire Island116 Properties
  • Tupper Lake102 Properties
  • Diamond Point91 Properties
  • Fishkill88 Properties
  • Fleischmanns86 Properties
  • Millbrook61 Properties
  • Riverhead58 Properties
  • Ellenville57 Properties
  • Chatham55 Properties
  • City of Gloversville51 Properties
  • Port Jefferson39 Properties
  • Croton-on-Hudson36 Properties
  • Findley Lake34 Properties
  • Adirondack32 Properties
  • Sodus Point29 Properties
  • Washingtonville19 Properties
  • Star Lake8 Properties