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Vacation rentals in Greenport

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Quick stats about vacation rentals in Greenport

  • Total vacation rentals

    Explore 140 vacation rentals in Greenport

  • Nightly prices starting at

    Greenport vacation rentals start at $130 per night before taxes and fees

  • Verified guest reviews

    Over 9,820 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Greenport vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Monthly stays, and Gym across Greenport rentals

  • 4.9 Average rating

    Greenport stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Greenport

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A wooden tray is centered on a neatly made bed, featuring a book and a coffee cup. The bed is dressed with a white quilt, and a softly textured pillow is placed against the headboard. A bedside lamp provides gentle illumination.
Guest suite in Southold
4.94 out of 5 average rating, 154 reviews

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact and provide a quiet and comfortable stay. About a five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard.

LocationValueIndoor spaces

Top guest favorite
A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.
Apartment in Southold
4.95 out of 5 average rating, 154 reviews

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

FamilyValueIndoor spaces

Guest favorite
A neatly arranged bedroom features a spacious bed dressed in white linens and accented with a textured throw pillow. Two windows provide natural light, flanked by simple wall sconces. A small shelf and minimal decor enhance the serene atmosphere.
Guest suite in Greenport
4.91 out of 5 average rating, 356 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

LocationValueGetting around

Guest favorite
A welcoming living area features a plush gray sofa and a light-colored armchair, accompanied by a rustic wooden coffee table. A dining table is visible in the background, and a well-equipped kitchen area is accessible. Natural light filters through multiple windows, enhancing the space.
Apartment in Greenport
4.96 out of 5 average rating, 269 reviews

Greenport Village View - Walk Downtown 2BR/1BA

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable. Please note this rental may not suitable for small children due to the staircase. A new baby gate has been installed at the top of the stairs. Village of Greenport Short Term Rental Permit #R26-021.

ValueLocationWifi

Top guest favorite
A charming historic boathouse features a steeply pitched roof with shingle siding and decorative trim. A white picket fence surrounds the property, while blooming shrubs enhance the entrance. A balcony adorned with planters awaits above the front door, complementing the inviting facade.
Home in Greenport
4.97 out of 5 average rating, 120 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

FamilyLocationIndoor spaces

Guest favorite
The front exterior of the bungalow is showcased, featuring a wooden fence that provides privacy and a garden filled with hydrangeas. The house displays large windows that invite natural light, set against a backdrop of gravel and greenery.
Home in Greenport
4.97 out of 5 average rating, 295 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

LocationFamilyBackyard

Guest favorite
A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.
Home in Greenport
4.95 out of 5 average rating, 393 reviews

The Sandpiper

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

FamilyValueParks

Guest favorite
A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.
Condo in Greenport
4.85 out of 5 average rating, 131 reviews

Beautiful condo on Long Islands Northfork

This condo is beautifully decorated and has a wonderful stone fire place. Gorgeous shiplap walls with Navy accents. There is also a new deck and wonderful dinning set outside. This unit has capabilities to be handicap accessible. Both bedroom have private bathrooms. The living room sectional opens up to a full sleeper making this condo able to sleep six people. All rooms have flat screen smart tv's.

LocationValueHospitality

Top guest favorite
The main bedroom features a spacious bed with a white comforter and dark accent pillows. Sunlight filters through sheer white curtains covering French doors, leading to the outdoors. Bright wooden floors add warmth, while a ceiling fan offers comfort.
Apartment in Greenport
4.97 out of 5 average rating, 133 reviews

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

ValueFamilyNearby

Guest favorite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in North Fork
4.96 out of 5 average rating, 212 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

FamilyValueQuiet

Superhost
A bright bedroom features white shiplap walls and large windows allowing natural light. A spacious bed is adorned with a textured white blanket and colorful decorative pillows. A vibrant area rug adds warmth, alongside a small table, a cozy armchair, and decorative plants.
Apartment in Greenport
4.84 out of 5 average rating, 195 reviews

Quiet Neighborhood and only steps to Town

Walk the 5 min into town with restaurants and bars, shops and cafes or enjoy the quiet neighbourhood and take a stroll down the block to watch the sailboats cruise into Sterling Harbor. This sunny apartment is situated on the second floor of a 1860's house on one of Greenport's prettiest streets. Its the true couples getaway!

FamilyLocationGetting around

Guest favorite
The exterior of a three-story house features light grey siding with turquoise shutters. A welcoming front porch contains multiple windows, and the entrance is accentuated by a small flight of stairs. Lush greenery surrounds the property, enhancing its appeal.
Apartment in Greenport
4.83 out of 5 average rating, 132 reviews

House on First

This beautiful upstairs apartment is 2 blocks from the charming Village of Greenport. It’s walking distance to many fine restaurants, beautiful beaches, antique carousel in Mitchell Park and ferry to Shelter Island. There’s a deck upstairs you can have your morning coffee before you head out on your next adventure!

LocationFamilyCleanliness

Popular amenities for Greenport vacation rentals

Self check-inMonthly staysGymBBQ grillLaptop-friendly workspace

Stay near Greenport's top sights

Noah's

224 locals recommend

Stars Cafe

35 locals recommend

The Market

15 locals recommend

Isola

15 locals recommend

Lido

13 locals recommend

Kontiki

12 locals recommend

Greenport house rentals

Top guest favorite
A vibrant orange car is parked on a gravel driveway in front of a navy blue house. Lush greenery surrounds the property, and a neatly manicured lawn extends beside a stone walkway leading to the entrance.
Home in North Fork
4.98 out of 5 average rating, 123 reviews

Beach House in L.I. Wine Country

FamilyLocationCheckout

Guest favorite
A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.
Home in Greenport
4.99 out of 5 average rating, 211 reviews

Greenport Village walking distance to all

LocationFamilyLayout

Top guest favorite
A vibrant flowering bush with large pink blooms is situated in the garden, adding color to the outdoor space. The wooden deck extends from the gazebo, and a rustic shed is visible in the background against a backdrop of green trees.
Home in Greenport
4.92 out of 5 average rating, 343 reviews

1830 Historic garden wing - walk to it all

ValueLocationCleanliness

Guest favorite
A modern kitchen showcases stainless steel appliances and white cabinetry. A spacious island is accented with a decorative vase of flowers. Wooden chairs provide seating at the island, and natural light floods the space through a nearby window.
Home in Greenport
4.92 out of 5 average rating, 50 reviews

Walk to town, Marina Views, Greenport Village

FamilyLocationQuiet

Top guest favorite
The exterior of the farmhouse is framed by well-maintained hedges, with a simple wooden staircase leading to the front door. Brightly lit windows are positioned symmetrically, highlighting the home's classic architecture. The surrounding greenery complements the inviting entrance.
Home in Greenport
4.92 out of 5 average rating, 131 reviews

Cozy Farmhouse Retreat in North Fork, NY

FamilyValueLaundry

Guest favorite
Home in Hampton Bays
4.85 out of 5 average rating, 156 reviews

Hamptons Oceanfront Oasis

ValueLocationAmenities

Top guest favorite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck
4.93 out of 5 average rating, 134 reviews

Modern farmhouse w/ pool, beach, horses and winery

FamilyLocationLayout

Top guest favorite
The living area features a combination of modern and historic elements, including a cozy seating arrangement with leather chairs and a round coffee table. Stained-glass windows add color, while a 65" television is mounted above a brick fireplace. Natural light illuminates the hardwood floors.
Home in Greenport
4.98 out of 5 average rating, 44 reviews

The Olde Church in Greenport

LocationBathroomHospitality

Other great vacation rentals in Greenport

Guest favorite
A modern outdoor space features a rectangular pool with crystal clear water, framed by a wooden deck. Comfortable seating arrangements, including two chairs with cushions and a dining table set for six, are complemented by an umbrella for shade.
Villa in Greenport
4.91 out of 5 average rating, 86 reviews

Year-Round Heated Pool Villa - 3 blocks from town

LocationFamilyPool

Guest favorite
Apartment in Southold
4.92 out of 5 average rating, 12 reviews

Kenney's Beach Loft - Vineyards, Horton Lighthouse

LocationValueNearby

Superhost
A well-lit living area features a large window and a glass door leading to the outdoor space. A modern fireplace is centered in the room, complemented by stylish furniture, including a curved sofa and a standing lamp. Art decor adds visual interest to the wall.
Home in North Fork
4.81 out of 5 average rating, 42 reviews

Stylish Getaway in Greenport

FamilyLocationBathroom

Guest favorite
Two white Adirondack chairs are positioned near a fire pit, offering a scenic view of the calm water and a partially cloudy sky at sunset. Pebbles and grassy areas surround the seating, enhancing the serene beach atmosphere.
Apartment in Southold
4.81 out of 5 average rating, 75 reviews

Incredible 2 Bedroom Waterfront Cottage!

ValueFamilyGetting around

Guest favorite
The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.
Condo in Greenport
4.89 out of 5 average rating, 196 reviews

Beautiful Waterview Condo on the North Fork of LI

LocationFamilyBeach

Superhost
A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.
Condo in Greenport
4.88 out of 5 average rating, 167 reviews

Waterfront Escape | Private Beach, Pool & Views

FamilyValueView

Top guest favorite
Cottage in North Fork
5 out of 5 average rating, 69 reviews

3 Min Walk to Beach| 1 Mile to Town | Fam-Friendly

LocationFamilyTV

Guest favorite
The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.
Guest suite in North Fork
4.88 out of 5 average rating, 737 reviews

Walk to Vineyards, Beaches, Farms & Town

ValueFamilyView

When is the best time to visit Greenport?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$333$303$313$358$441$509$508$525$462$402$355$334
Avg. temp31°F33°F40°F50°F60°F70°F76°F74°F68°F56°F46°F37°F

Frequently Asked Questions

  • What are the best places to stay in Greenport?

    Many travelers choose accommodations around the village center for walkable access to shops, dining, and harbor views. Waterfront areas and neighborhoods just outside the center are also popular for those seeking quieter stays.

  • What are the best things to do in Greenport with kids?

    Families frequently suggest a ride on the Greenport Carousel, exploring interactive exhibits at the East End Seaport Museum, and relaxing at Mitchell Park. Waterfront promenades and boat tours are also popular with children.

  • What are some of the best things to do in Greenport?

    Explore Greenport’s working waterfront, browse galleries, and stop by the historic carousel. Locally owned shops and wine tasting rooms around the village square are often recommended.

  • How is the weather in Greenport?

    Greenport experiences chilly winters around 24–38°F (−4–4°C) and warm summers reaching 68–83°F (20–29°C). Spring and fall have comfortable temperatures, making them popular times for exploring outdoors.

  • When is the best time to visit Greenport?

    Late spring through early fall is often recommended for milder weather and outdoor festivals. The village feels lively with markets, dining on patios, and events celebrating the local harvest.

  • What are the best places to visit in Greenport?

    Greenport has a classic carousel, the East End Seaport Museum, and Mitchell Park, which are frequently suggested. The marina area and historic streets lined with independent shops also draw many visitors.

  • What are some hiking trails in Greenport?

    Explore village paths along the waterfront, or venture to nearby preserves with nature trails and birdwatching areas. Many visitors enjoy gentle walks near the beach and shaded routes through local parks.

  • What are some family activities we can do in Greenport?

    Families can ride the Greenport Carousel, picnic in Mitchell Park, or explore interactive exhibits at local museums. Boat rides, fishing excursions, and ice cream shops are also popular with children.

  • What are some of the best day trip ideas from Greenport?

    Consider exploring local vineyards, historic lighthouses, or nearby farm stands known for seasonal produce. Beaches and nature reserves around the North Fork are also frequently suggested for day adventures.

  • Are there any pet friendly accommodations available in Greenport?

    Greenport has many pet-friendly rentals throughout the village and surrounding areas. Look for listings that welcome pets, and enjoy exploring nearby parks and waterfront spaces with your companion.

  • What are some local tips for visiting Greenport?

    Arrive early on weekends for easier parking, and consider bringing a bike to explore quiet streets and harborside views. Locals often suggest trying the seasonal seafood and visiting neighboring vineyards.

  • What is Greenport known for?

    Greenport is known for its maritime history, vibrant local arts, and a lively dining scene rooted in coastal traditions. Visitors often enjoy its wine country proximity and classic seaside village atmosphere.

  • What are the best hidden gems to explore in Greenport?

    Consider browsing small galleries, visiting the camera obscura at Mitchell Park, or sampling treats at family-run bakeries. The historic railroad dock and pocket parks around the harbor are quieter local favorites.

  • What are the best foods to try in Greenport?

    Greenport is known for fresh seafood such as oysters and clam chowder, alongside locally made ice cream and bakery treats. The village also has restaurants featuring North Fork wines and produce.

  • What should I bring for a trip to Greenport?

    Pack layers for variable weather, especially a light jacket even in summer evenings. Comfortable walking shoes are helpful for exploring, and a hat or sunscreen can be useful for harbor strolls or nearby beaches.

  • What is the nightlife in Greenport like?

    Greenport’s nightlife is known for relaxed wine bars, lively taverns, and live music in local venues. Many spots focus on local flavors, creating a welcoming atmosphere for a range of tastes.

  • What are the most popular events or festivals in Greenport?

    Greenport hosts maritime celebrations, arts festivals, and food events during summer and fall. Seasonal farmers markets and harvest festivals are often highlights around late summer and early autumn.

  • Are there family friendly vacation rentals in Greenport?

    Greenport has many family-friendly vacation rentals, including homes and apartments with extra space, kitchens, and easy access to parks. Many listings offer outdoor areas for kids and are near waterfront attractions.

Destinations to explore