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
    $1,345
  • Sunny Room in Sag Harbor
     Family Stay
    Booking.com
    From
    $300
  • Beautiful French Country Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $573
  • Sag Harbor Great Loc + Pool
     Country House
    Booking.com
    From
    $475
  • East Hampton Classic
    Excellent4br Home/Apartment
    Flipkey
    From
    $960
  • Sag Harbor Privacy 6Min Bridgehampton
     Country House
    Booking.com
    From
    $475
  • Sag Harbor Village House of Love
     2br Home/Apartment
    HolidayLettings
    From
    $641

Check prices for these upcoming dates

Greenport Vacation Rentals with a Pool

  • Chic Shelter Island Home, Pool and Gardens
    Excellent3br Home/Apartment
    Airbnb
    From
    $1,040
  • Water View First Floor Condo
    Good2br Home/Apartment
    Airbnb
    From
    $565
  • Charming Shelter Island Farmhouse Pool
     3br Home/Apartment
    Airbnb
    From
    $650
  • Sunny Country cottage with pool
    ExcellentCottage
    Airbnb
    From
    $215

Greenport Vacation Rentals with Wi-Fi

  • charming home with a peaceful vibe
    Excellent2br Home/Apartment
    Airbnb
    From
    $184
  • Charming Historic Home - Heart of Greenport
    Good4br Home/Apartment
    Airbnb
    From
    $762
  • Beautiful apartment close to everything
    ExcellentHome/Apartment
    Airbnb
    From
    $339
  • Historic 4 Bedroom Greenport House
    Excellent5br Home/Apartment
    Airbnb
    From
    $579

Greenport Pet-Friendly Vacation Rentals

  • Amazing Hampton's Styled Getaway
     6br Home/Apartment
    HolidayLettings
    From
    $1,549
  • Hamptons Lofty Beach Barn - Pet Friendly
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $1,288
  • Sag Harbor Waterfront Dock, Pool Kayak & Paddleboards Aug10-17 & Labor Day avil
     8br Home/Apartment
    HolidayLettings
    From
    $2,975
  • 5 Min to Bridgehampton n Sag Harbor 8 Min Ocean
     4br Home/Apartment
    HolidayLettings
    From
    $2,605

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
91 º48
4
81 º32
2
70 º10
4
63 º18
2
59 º-2
2
68 º9
3
63 º19
3
75 º27
2
90 º41
1
90 º48
1
99 º55
1
95 º55
2
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Greenport. The hottest month in Greenport is June, when temperatures peak at 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

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston

Destinations near Greenport

  • New York18,240 Properties
  • Brooklyn10,467 Properties
  • Niagara Falls4,610 Properties
  • Queens2,938 Properties
  • Lake Placid1,528 Properties
  • Ithaca1,514 Properties
  • Montauk1,402 Properties
  • Rochester879 Properties
  • Sag Harbor857 Properties
  • Lake George Village812 Properties
  • Amagansett763 Properties
  • Hampton Bays697 Properties
  • Southampton638 Properties
  • Springs628 Properties
  • Albany620 Properties
  • Hudson586 Properties
  • Woodstock558 Properties
  • Ellicottville558 Properties
  • Cooperstown556 Properties
  • Village of East Hampton552 Properties
  • Lake George544 Properties
  • Saugerties542 Properties
  • Hunter534 Properties
  • Canandaigua463 Properties
  • Windham434 Properties
  • Ocean Beach432 Properties
  • Saranac Lake428 Properties
  • Geneva410 Properties
  • Bridgehampton392 Properties
  • Kingston386 Properties
  • Beacon383 Properties
  • Chautauqua364 Properties
  • Watkins Glen363 Properties
  • Wilmington360 Properties
  • Staten Island353 Properties
  • Penn Yan343 Properties
  • Cherry Grove338 Properties
  • Syracuse337 Properties
  • Noyack330 Properties
  • Hammondsport324 Properties
  • Buffalo315 Properties
  • New Paltz311 Properties
  • East Quogue306 Properties
  • Yonkers301 Properties
  • Alexandria Bay298 Properties
  • Watermill291 Properties
  • Southold286 Properties
  • Chestertown282 Properties
  • Cortland273 Properties
  • Bolton Landing273 Properties
  • Long Beach271 Properties
  • Queensbury270 Properties
  • Wainscott270 Properties
  • Warrensburg264 Properties
  • Plattsburgh259 Properties
  • Binghamton251 Properties
  • White Plains241 Properties
  • Shelter Island237 Properties
  • Auburn236 Properties
  • Old Forge234 Properties
  • Rhinebeck229 Properties
  • Westhampton Beach221 Properties
  • Poughkeepsie215 Properties
  • Amherst214 Properties
  • North Creek211 Properties
  • Catskill203 Properties
  • Skaneateles203 Properties
  • Westhampton202 Properties
  • Trumansburg200 Properties
  • Saratoga Springs188 Properties
  • Pulaski184 Properties
  • Schroon Lake181 Properties
  • Dundee170 Properties
  • Clayton161 Properties
  • Quogue146 Properties
  • Fishkill138 Properties
  • Newburgh138 Properties
  • Fire Island118 Properties
  • Tupper Lake105 Properties
  • Mount Vernon101 Properties
  • Fleischmanns90 Properties
  • Millbrook73 Properties
  • Diamond Point73 Properties
  • Riverhead65 Properties
  • Ellenville53 Properties
  • Chatham52 Properties
  • City of Gloversville47 Properties
  • Port Jefferson41 Properties
  • Findley Lake37 Properties
  • Croton-on-Hudson33 Properties
  • Adirondack30 Properties
  • Sodus Point25 Properties
  • Washingtonville20 Properties
  • Star Lake8 Properties