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Holiday houses in Greenport

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Quick stats about holiday rentals in Greenport

  • Total holiday rentals

    Explore 140 holiday rentals in Greenport

  • Nightly prices starting at

    Greenport holiday rentals start at $186 AUD per night before taxes and fees

  • Verified guest reviews

    Over 9,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Greenport holiday 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 holiday rentals in Greenport

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

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Top Guest favourite
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
4.97 out of 5 average rating, 37 reviews

Beautiful 2 Bedroom, 2 Bath Greenport Village Loft

Enjoy this newly renovated 2 bedroom 2 bath loft apartment centrally located in the village of Greenport. Conveinient 5 minute walk to Front street, Main street shops, restaurants, bars and across from park/playground. Private rear deck for outdoor dining and a covered front porch for a glass of wine or morning coffee. Parking for 2 midsize cars in driveway. Power outlet available for EVs. Private yard with BBQ, firepit, adirondack chairs grassy area and lounges for sunning, reading or napping.

Guest favourite
A bright living space is featured, furnished with two light-colored chairs and a dark coffee table. A flat-screen television is mounted on the wall. A doorway leads to a bedroom, while natural light filters in through the windows, illuminating the neutral decor.
Home in Greenport
4.95 out of 5 average rating, 263 reviews

Aqua Vista

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 rental is 2nd floor apartment (only). Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy. Located right in Greenport. Walking distance to all the restaurants, bars, shopping, coffee shops.

Top Guest favourite
A charming blue house is framed by lush green trees, with a welcoming front porch. Large windows invite natural light, while a white picket fence complements the tranquil outdoor setting. The spacious yard features vibrant grass, enhancing the peaceful atmosphere.
Home in Southold
4.96 out of 5 average rating, 54 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

𓇼Walk to the Beach! ༄Location: quiet oasis by nature preserve, vineyards, breweries, farm stands, restaurants + attractions, 5 min to Greenport Village + Southold 𓇼Firepit, outdoor dining with string lights, grill, beverage cooler ༄Equipped kitchen w/blender, coffee, waffle maker + more! 𓇼Bathrooms w/heated floors + a clawfoot soaking tub (Please note there is only 1 shower) ☼Family Friendly: Board games, packNplay, high chair, beach chairs + toys ༄Kayak + bikes 𓇼Smart TVs

Guest favourite
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, 352 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!

Top Guest favourite
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, 118 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.

Top Guest favourite
Cottage in North Fork
5 out of 5 average rating, 66 reviews

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

<b>The Greenport Beach Cottage</b> • Bright & updated 800 sq ft coastal cottage • 3 minute walk to beach, 4 minute drive to town • Sleeps up to 5 guests • Family-friendly amenities • Fully fenced in (fence not pictured) backyard with 2 fire pits, charcoal & gas grill, outdoor shower • Garage with 4 beach cruiser bikes, Foosball table & small gym area Book your coastal getaway now- only a few summer weekends remaining! IG: @thegreenportbeachcottage

Guest favourite
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, 294 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!

Top Guest favourite
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, 40 reviews

The Olde Church in Greenport

This one of a kind converted 1867 Church is historic, stylish and close to everything in Greenport, making it easy to plan and enjoy your visit. Located in the heart of Greenport it is walking distance to all restaurants, shops, a local beach, the LIRR and the Jitney stop. This spacious home has maintained some of the most beautiful pieces of the past alongside modern amenities to make your stay memorable and comfortable.

Top Guest favourite
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, 129 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!

Top Guest favourite
Home in Greenport
5 out of 5 average rating, 26 reviews

Greenport Gem

Enjoy a stylish experience at this newly renovated centrally-located in the village of Greenport. Located only one block from Front Street and Main Street, you will be able to walk anywhere in downtown Greenport. Less than a 5 minute walk to the Shelter Island Ferry and LIRR. Parking for 2 cars. Queen sized air mattress and extra bedding are available.

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
4.83 out of 5 average rating, 193 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!

Top Guest favourite
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, 121 reviews

Beach House in L.I. Wine Country

Time to wine 🍷 down and make your way to the scenic North Fork. A clean and clutter-free beach house awaits. The Navy House is centrally located in a quiet residential enclave, steps away from Norman E. Klipp Marine Park (aka Gull Pond Beach) and a short drive to Greenport’s Historic Village, vineyards and farmstands.

Popular amenities for Greenport holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Greenport

Top Guest favourite
Home in North Fork
4.98 out of 5 average rating, 60 reviews

Corwin House

Top Guest favourite
A light-filled living room features a comfortable gray sofa adorned with decorative cushions. Two stylish chairs, with soft white covers, are positioned beside a coffee table that includes decorative books. Warm lamps create a cozy atmosphere, while a patterned rug adds texture beneath.
Apartment in Greenport
4.99 out of 5 average rating, 69 reviews

The Crow's Nest

Guest favourite
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
4.9 out of 5 average rating, 84 reviews

Year-Round Heated Pool Villa - 3 blocks from town

Guest favourite
Apartment in Southold
4.86 out of 5 average rating, 7 reviews

Kenney's Beach Loft - Vineyards, Horton Lighthouse

Guest favourite
The kitchen features light grey cabinets with white countertops, complemented by stainless steel appliances. A small dining table with two stools is positioned near the window, allowing natural light to brighten the space. Hardwood flooring provides a warm touch to the modern design.
Apartment in Greenport
4.9 out of 5 average rating, 31 reviews

Charming 2 Bedroom Apt in Dwntwn Greenport

Top Guest favourite
A private deck area is showcased, featuring a comfortable seating arrangement with a wicker sofa and two chairs, accentuated by decorative cushions. A square table with a woven texture sits at the center, surrounded by colorful planters filled with blooming flowers and greenery.
Home in Greenport
4.97 out of 5 average rating, 67 reviews

modern 3 bedroom home with fireplace

Guest favourite
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, 73 reviews

Incredible 2 Bedroom Waterfront Cottage!

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
4.82 out of 5 average rating, 39 reviews

Stylish Getaway in Greenport

When is the best time to visit Greenport?

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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.

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