Places to stay in Greenport

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).

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.

4.96 out of 5 average rating, 105 reviews

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.

Guest suite in North Fork

A vibrant seasonal market is displayed, featuring a yellow vintage truck parked in the foreground. Colorful chrysanthemums and pumpkins line the gravel pathway, while a rustic building adorned with decorative elements stands in the background against a cloudy sky.

4.88 out of 5 average rating, 667 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!

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Other great vacation rentals in Greenport

An outdoor seating area is presented with woven furniture featuring bright red cushions. A rectangular table is centered on a striped rug, surrounded by several chairs and ottomans. A grill is positioned in the corner, with a fire pit adjacent, enhancing the space's functionality.

5 out of 5 average rating, 19 reviews

Newly renovated farmhouse - steps to Village

Sarah JaneRating, 5 stars1 month ago

Cannot say enough great things about this house. I’ve stayed in many AirBnBs and other home rentals over the years and this was one of my absolute favorites. The house is beautifully updated and was extremely clean. The kitchen and bathrooms are gorgeous and have everything you need. Beds were so comfortable and the room darkening shades are a rare find in a vacation rental. Close to Greenport town and lots of wineries. Backyard was beautifully landscaped and was amazing for our dogs to run around. We will definitely stay here again!

The exterior features a serene swimming pool surrounded by a well-maintained patio. Multiple seating areas are arranged near the pool, along with a BBQ station. A charming shed is visible in the background. Lush greenery and trees frame the property, offering privacy and shade.

4.89 out of 5 average rating, 9 reviews

Quaint Chalet w/Salt-heated Pool

VaughnRating, 5 stars8 months ago

Wonderful weekend stay. Charming.

A bright bedroom featuring a spacious bed with light linens. A wooden bench is positioned at the foot of the bed beside a textured area rug. An armchair sits next to a potted plant near a window, allowing natural light to enhance the room's atmosphere.

4.98 out of 5 average rating, 134 reviews

Cosy North Fork Cottage with large backyard

SarahRating, 5 stars1 week ago

Absolutely gorgeous home - the decor, linens, and amenities were top notch. Beautiful, private large backyard where we spent much of our time. As a family of 6, we utilized all of the rooms and it was the perfect space to bond and hang out. Walkable to the beach, park and all of the great restaurants in town and just a short drive to so many awesome spots in Orient and the north fork. Would love to visit again!

4.95 out of 5 average rating, 44 reviews

modern 3 bedroom home with fireplace

MarielleRating, 5 stars1 month ago

We had a wonderful stay in Greenport! The house was comfortable and very well kept. Everything was pristine. The location was great- a few short blocks into town for shops and restaurants. We had an issue with the fire detector sounding and Kim was kind enough to compensate us for the issue. She is a great and responsive host. Would definitely stay here for our next visit!

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.

4.84 out of 5 average rating, 170 reviews

Quiet Neighborhood and only steps to Town

TeresaRating, 5 stars2 days ago

Karolina was a very attentive and helpful host! Her home was beautiful and very clean. Super close to Greenport village (within walking distance). It is perfect for a short stay. 😊 We enjoyed our time there greatly! Thank you so much, Karolina!

4.94 out of 5 average rating, 103 reviews

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

CarolRating, 5 stars4 weeks ago

Great accommodations for a 2 person getaway! Peaceful, quiet, beautiful location within walking distance to Greenport village. Check-in and check out was simple! The apartment is uncluttered and very clean and has everything you need for a comfortable stay!

The kitchen features a central island with a blue finish and ample counter space. Modern appliances, including a white refrigerator and a gas stove, are present. Light is provided by windows, creating a bright environment. Elegant wooden flooring complements the overall design.

5 out of 5 average rating, 17 reviews

Sterling Harbor 2 Bedroom Apt

AlizaRating, 5 stars2 weeks ago

Perfect place to unwind after a long day of exploring the North Fork 😍 Steps away from downtown Greenport and its charming restaurants, shops and bars. Not to mention we could find everything we needed and felt right at home in the beautifully appointed apartment :)