Holiday houses in Greenport West

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Top-rated holiday rentals in Greenport West

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

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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 North Fork
4.81 out of 5 average rating, 220 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

Guest favourite
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 North Fork
4.91 out of 5 average rating, 117 reviews

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

Superhost
A riverfront deck is furnished with two lounge chairs and a glass table, surrounded by lush greenery and trees. The view overlooks a calm stretch of the Patchogue River, creating a serene environment for relaxation and enjoyment of nature.
Cottage in Westbrook
4.87 out of 5 average rating, 186 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Top Guest favourite
A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.
Apartment in The Hamptons
4.98 out of 5 average rating, 198 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Guest favourite
A cozy living area features a comfortable gray sofa adorned with patterned pillows. A light-colored side table and an illuminated lamp create a soft glow. A decorative coffee table sits in front, accompanied by a potted plant in the corner, adding a touch of greenery.
Apartment in North Fork
4.92 out of 5 average rating, 119 reviews

Private 1st flr apt w/ patio 3 blocks from beach

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

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 North Fork
4.91 out of 5 average rating, 339 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!

Guest favourite
A cozy living area features a brown sectional sofa adorned with patterned throw pillows. A black coffee table sits on a striped area rug, providing a neutral contrast to the light hardwood flooring. Natural light filters through multiple windows, enhancing the welcoming ambiance.
Home in North Fork
4.93 out of 5 average rating, 212 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

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 North Fork
4.97 out of 5 average rating, 115 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
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 North Fork
4.97 out of 5 average rating, 278 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!

Guest favourite
A clear blue saltwater pool is surrounded by a landscaped yard featuring green grass and shrubs. Several lounge chairs are positioned nearby under light blue umbrellas, providing shade. A two-story house is visible in the background, framed by tall trees.
Home in North Fork
4.9 out of 5 average rating, 230 reviews

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Top Guest favourite
Home in North Fork
4.99 out of 5 average rating, 103 reviews

Greenport Village Rental

Exquisitely renovated traditional style home offers an open concept first floor, expansive rear deck covered by fixed-in-place awning with a meticulously landscaped backyard and outdoor shower. Located on charming 5th avenue in Greenport Village, Mitchell Park, renowned restaurants and the best of what the North Fork has to offer is only a short walk away.

Guest favourite
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, 708 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Popular amenities for Greenport West holiday rentals

When is the best time to visit Greenport West?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Greenport West?

    Greenport West has more than 260 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there Greenport West vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 100 vacation homes with pools in Greenport West, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Greenport West?

    Make yourself at home in Greenport West by choosing from our most frequently booked neighborhoods. We have over 530 vacation rentals in Dering Harbor, over 530 vacation rentals in Greenport, and over 530 vacation rentals in Greenport West.

  • Do condo rentals in Greenport West have wifi?

    Absolutely! We offer over 20 condo rentals with wifi in Greenport West. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Greenport West have air conditioning?

    Absolutely! We offer over 20 condo rentals with air conditioning in Greenport West. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Greenport West?

    Four-legged friends are welcome in Greenport West. Choose from more than 100 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Greenport West?

    Yes! Work meets play with ease at over 160 vacation rentals in Greenport West featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do condo rentals in Greenport West have free parking?

    Absolutely! We offer over 20 condo rentals with free parking in Greenport West. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Greenport West have a kitchen?

    Absolutely! We offer over 190 house rentals with a kitchen in Greenport West. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Condo Rentals in Greenport West?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Greenport West

  • Total holiday rentals

    Explore 320 holiday rentals in Greenport West

  • Nightly prices starting at

    Greenport West holiday rentals start at $164 AUD per night before taxes and fees

  • Verified guest reviews

    Over 14,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    260 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    310 of Greenport West holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Greenport West rentals

  • 4.9 Average rating

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

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