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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 G$27,146 GYD 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, 153 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.

LocationFamilyLong stay

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, 153 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!

ValueLocationHiking

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!

FamilyLocationTV

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.

ValueFamilyOutdoor spaces

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.

LocationFamilyBiking

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!

FamilyValueDecor

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.

FamilyValueParking

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

This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

ValueFamilyKitchen

Top guest favorite
A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.
Apartment in Greenport
4.96 out of 5 average rating, 174 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

ValueFamilyNearby

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, 132 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!

LocationValueHeating

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, 211 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.

FamilyValueBathroom

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!

FamilyValueAir conditioning

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
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, 130 reviews

Cozy Farmhouse Retreat in North Fork, NY

LocationFamilyNearby

Top guest favorite
Home in Greenport
4.93 out of 5 average rating, 135 reviews

Chic greenport village home

LocationFamilyGrill

Guest favorite
Home in Hampton Bays
4.85 out of 5 average rating, 155 reviews

Hamptons Oceanfront Oasis

LocationValueWalkability

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

FamilyLocationPool

Superhost
A light-filled living space features a brown sofa adorned with aqua cushions, accented by a decorative throw. A wooden coffee table sits atop a soft rug, surrounded by various decorative items. An air conditioning unit and a fan are mounted on the wall, enhancing comfort.
Home in Greenport
4.83 out of 5 average rating, 230 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

ValueFamilyDecor

Top guest favorite
A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.
Home in North Fork
4.97 out of 5 average rating, 218 reviews

Private Oasis W/Stunning Vinyard and Pool Views

ValueLocationGetting around

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, 43 reviews

The Olde Church in Greenport

LocationQuietView

Guest favorite
Home in Greenport
4.87 out of 5 average rating, 15 reviews

Bayview house with salt water pool & private chef

LocationFamilyBackyard

Other great vacation rentals in Greenport

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
4.86 out of 5 average rating, 130 reviews

Beautiful condo on Long Islands Northfork

ValueLocationCheckout

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, 166 reviews

Waterfront Escape | Private Beach, Pool & Views

FamilyLocationCheckout

Top guest favorite
An expansive view of the ocean under a bright blue sky, featuring wispy clouds. The shoreline is lined with gentle waves, and a grassy area is visible in the foreground, leading down to the water.
Condo in Greenport
4.89 out of 5 average rating, 278 reviews

Sound Front Condominium

LocationFamilyLaundry

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

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

FamilyLocationComfort

Guest favorite
Apartment in Southold
4.89 out of 5 average rating, 9 reviews

Kenney's Beach Loft - Vineyards, Horton Lighthouse

FamilyLocationBeach

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!

FamilyValueNearby

Guest favorite
A charming Victorian home features a blue exterior with white accents and a welcoming porch. Lush greenery surrounds the entrance, enhancing the inviting atmosphere. The property includes a second-story balcony, providing outdoor space to enjoy the surrounding neighborhood.
Apartment in Greenport
4.94 out of 5 average rating, 65 reviews

Lovely 1st floor of farmhouse, wineries/downtown

LocationValueSleep quality

Guest favorite
A charming two-story house features a covered front porch with white railings and planters flanking the black front door. Well-manicured grass borders a stone walkway leading to the entrance, with a seating bench visible on the porch. Neighborhood structures are seen in the background.
Loft in Greenport
4.95 out of 5 average rating, 38 reviews

Beautiful 2 Bedroom, 2 Bath Greenport Village Loft

FamilyLocationQuiet

When is the best time to visit Greenport?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$69,537 GYDG$63,272 GYDG$65,360 GYDG$74,757 GYDG$92,089 GYDG$106,289 GYDG$106,080 GYDG$109,630 GYDG$96,474 GYDG$83,945 GYDG$74,131 GYDG$69,745 GYD
Avg. temp0°C1°C4°C10°C16°C21°C24°C24°C20°C14°C8°C3°C

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