Vacation rentals in Greenport West

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Top-rated vacation rentals in Greenport West

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

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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 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.

Guest favorite
A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.
Home in The Hamptons
4.95 out of 5 average rating, 480 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Guest favorite
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.

Superhost
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 North Fork
4.96 out of 5 average rating, 248 reviews

Aqua Vista

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 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 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 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 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 favorite
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, 229 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 favorite
The living area features a vaulted ceiling with bright natural light streaming through large windows. A cozy seating arrangement includes a light grey couch and a comfortable chair. A stylized coffee table sits in the center, with a dining table set for two nearby.
Cottage in East Lyme
4.97 out of 5 average rating, 298 reviews

Your Nest Near The Beach

Welcome to A Shore Thing, a retro modern beach cottage. This bright and cheerful escape is perfectly located for exploring the shoreline. Whether you are visiting in the summer for sun, surf and sand or in the quieter off-season, you will find the shoreline is packed with an incredible array of inviting destinations. The cottage is just 3/4 of a mile from the beautiful private sandy beach.

Top guest favorite
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.

Top guest favorite
The farmhouse, constructed in 1856, is showcased with its classic white exterior and black accents. Large windows allow natural light to fill the space, while lush greenery surrounds the property. A pebble pathway leads to the entrance, enhancing the inviting atmosphere.
Home in Old Lyme
4.97 out of 5 average rating, 205 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Guest favorite
A charming historic bungalow is presented with a shingle exterior and turquoise accents. The entrance is framed by flower boxes, and brick paving extends to the driveway. Lush greenery surrounds the property, while clear blue skies complement the inviting facade.
Home in North Fork
4.99 out of 5 average rating, 206 reviews

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.

Guest favorite
An open living space features wooden walls and bright hardwood floors. A cozy seating arrangement includes a sofa and a side table. A dining area with blue chairs is visible next to a large window, while a brick fireplace adds a rustic touch to the room.
Cottage in South End
4.9 out of 5 average rating, 186 reviews

Cozy Cottage on the Great Pond near beach.

In the heart of wine country is the adorable , nautical inspired cottage surrounded by nature, on a beautiful freshwater pond, a quick walk or bike ride away from a beautiful beach on Long Island Sound. Hiking, fishing, wine tours, farmstands abound!

Popular amenities for Greenport West vacation 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 Greenport West, over 530 vacation rentals in Dering Harbor, and over 530 vacation rentals in Greenport.

  • 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 house rentals in Greenport West have air conditioning?

    Absolutely! We offer over 200 house 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 cottage rentals in Greenport West have free parking?

    Absolutely! We offer over 10 cottage 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 House Rentals in Greenport West?

    Enhance your stay in our House Rentals with the most popular amenities: over 190 homes with a kitchen, over 200 homes with wifi, over 200 homes with air conditioning, over 200 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Greenport West

  • Total vacation rentals

    Explore 320 vacation rentals in Greenport West

  • Nightly prices starting at

    Greenport West vacation rentals start at ﺩ.ﺇ404 per night before taxes and fees

  • Verified guest reviews

    Over 14,960 verified reviews to help you choose

  • Family-friendly vacation rentals

    260 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 100 rentals that welcome pets

  • Vacation 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 vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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