Vacation rentals in Greenport West

4.91 out of 5 average rating, 107 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 sandy beach stretches along the Long Island Sound, bordered by greenery. A wooden boardwalk leads to the shore, with lounge chairs positioned for sunbathing. In the background, several buildings are nestled among the trees, completing the tranquil seaside scene.

Condo in North Fork

4.85 out of 5 average rating, 136 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

A welcoming entrance features a white picket fence adorned with blooming rose bushes. The front door is framed by classic columns, leading to a well-maintained brick pathway that guides guests to the home. Sunlight enhances the charming facade of the historic boathouse.

4.98 out of 5 average rating, 102 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, and recently & lovingly fully renovated and restored. 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.

4.92 out of 5 average rating, 140 reviews

A serene ocean view features gentle waves lapping against a rocky shoreline, with a soft sunset illuminating the sky. Silhouettes of distant rocks and subtle ripples on the water enhance the tranquil atmosphere.

Condo in North Fork

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Guest suite in North Fork

A modern bathroom features a walk-in shower with a glass enclosure and white subway tiles. A double vanity with sleek storage sits opposite a toilet. Decorative photos are arranged on the dark wall above the vanity, while a light fixture illuminates the space. A rug lies on the floor.

4.91 out of 5 average rating, 317 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!

4.94 out of 5 average rating, 187 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).

An open kitchen space features modern appliances, including a stainless steel stove and ample counter space. Barstools are positioned at a breakfast bar, while natural light illuminates the area through several windows. Warm wood flooring complements the neutral-colored walls.

4.93 out of 5 average rating, 115 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

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.

4.97 out of 5 average rating, 262 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!

A landscaped backyard features a refreshing saltwater pool surrounded by lounge chairs and umbrellas. Lush greenery enhances the private atmosphere, while flowers add touches of color along the paved pathway leading to the pool area. Bright, clear skies create an inviting outdoor scene.

4.9 out of 5 average rating, 215 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).

4.96 out of 5 average rating, 105 reviews

An open living space is displayed, featuring light wooden flooring and a wooden slatted divider. A dining area is visible with a large table and high-backed chairs. A sideboard stands against the divider, enhancing the separation between areas.

Apartment in North Fork

Junior 1-BR in the heart of Greenport Village

Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

A spacious, private garden is featured, showcasing well-maintained green grass and mature trees surrounding an old shed. Two lounge chairs are positioned in the sunlight, creating a relaxing spot. A section of the fence is adorned with an American flag, adding a touch of character.

4.92 out of 5 average rating, 305 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.

Apartment in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.91 out of 5 average rating, 247 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

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Popular amenities for Greenport West vacation rentals

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Other great vacation rentals in Greenport West

A view from the front porch is displayed, showcasing a spacious area with white railings and a swing. Colorful flower beds line the edge of the grass, while vehicles can be seen passing by on the street. The distant marina is visible under a clear sky.

5 out of 5 average rating, 23 reviews

Elegant Greenport Victorian -Winter Harbor House

A wooden staircase descends towards a sandy beach, flanked by rows of lounge chairs. The calm water stretches to the horizon, transitioning from light blue to turquoise near the shore. Gentle waves lap against the shoreline under a clear blue sky.

4.95 out of 5 average rating, 42 reviews

Greenport Getaway - North Fork Rental

The kitchen features elegant cabinetry and a spacious island topped with patterned stone. Modern appliances, including a large refrigerator and microwave, are visible. Windows illuminate the space, providing views into the yard and outdoor seating area.

4.89 out of 5 average rating, 9 reviews

The Northfork Nook: Pool & Family Friendly!

An aerial view of a marina reveals multiple docks filled with boats and yachts, alongside a vibrant waterfront community. The shimmering water reflects the clear blue sky, while the greenery of trees borders the landscape, showcasing a mix of natural and developed areas.

4.99 out of 5 average rating, 93 reviews

Greenport Village Rental

A bright bedroom features a spacious bed adorned with a cozy knitted throw. Colorful decorative pillows add a friendly touch. A small table and a chair create a functional space. Light from a window illuminates the soft wall paneling, enhancing the serene ambiance.

Apartment in North Fork

4.84 out of 5 average rating, 170 reviews

Quiet Neighborhood and only steps to Town

4.94 out of 5 average rating, 103 reviews

Apartment in North Fork

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

An outdoor dining area is set beneath a striped umbrella, surrounded by greenery. A wooden table with several chairs is positioned nearby, with a hammock visible in the distance. A heated saltwater pool glistens under the sun, complemented by lounge chairs along the poolside.

5 out of 5 average rating, 5 reviews

Delightful Cape House in Greenport