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Vacation rentals in Greenport

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Top-rated vacation rentals in Greenport

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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, 116 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.

Top guest favorite

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

4.98 out of 5 average rating, 178 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

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, 115 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.

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

4.94 out of 5 average rating, 204 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).

A wooden tray is centered on a neatly made bed, featuring a book and a coffee cup. The bed is dressed with a white quilt, and a softly textured pillow is placed against the headboard. A bedside lamp provides gentle illumination.

Guest suite in South End

4.94 out of 5 average rating, 141 reviews

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

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

4.96 out of 5 average rating, 111 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.

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

Home in North Fork

4.93 out of 5 average rating, 145 reviews

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

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, 270 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 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, 223 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

A vibrant flowering bush with large pink blooms is situated in the garden, adding color to the outdoor space. The wooden deck extends from the gazebo, and a rustic shed is visible in the background against a backdrop of green trees.

Home in North Fork

4.92 out of 5 average rating, 319 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.

Top guest favorite

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 North Fork

4.96 out of 5 average rating, 109 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!

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, 693 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!

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Greenport vacation rentals

Laptop-friendly workspace

Family friendly vacation rentals in Greenport

A well-lit bedroom features a spacious bed adorned with crisp white linens. Natural light enters through two windows, illuminating a rug beneath. A small table and a decorative plant are positioned beside the bed, creating a serene and inviting atmosphere.

Home in North Fork

4.96 out of 5 average rating, 49 reviews

Greenport Getaway - North Fork Rental

An aerial view of a heated inground pool is shown, surrounded by a stone patio and green grass. Red and white beach balls float on the water. A covered seating area is visible, along with several lounge chairs under striped umbrellas.

Villa in The Hamptons

4.98 out of 5 average rating, 41 reviews

Luxe| Pool|Game Room |Outdoor Movie|HotTub|Firepit

A light-filled living area features a striped sectional sofa accompanied by a decorative lamp. Wall art in soft colors is displayed above a wooden table, which holds a small boat sculpture. The flooring is comprised of warm wood tones, enhancing the inviting space.

Home in North Fork

4.91 out of 5 average rating, 32 reviews

Charming Home in Village Center!

Guest suite in North Fork

4.8 out of 5 average rating, 44 reviews

Garden Studio with private entrance

A gated patio area is surrounded by lush greenery, featuring tall plant hedges on one side. Two wooden arches frame the entrances, leading to a scenic garden path. A small seating area with a patterned cushion is set in the foreground, inviting relaxation.

Home in The Hamptons

5 out of 5 average rating, 3 reviews

Cozy Hamptons Cottage

The front exterior of the home is framed by lush greenery and a flower-lined pathway made of stone. Two trees add natural shade, while a charming yellow door welcomes guests. A fenced yard and gravel accents enhance the inviting entrance.

Home in North Fork

4.93 out of 5 average rating, 120 reviews

Maritime Village Getaway with Backyard

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in North Fork

4.88 out of 5 average rating, 149 reviews

Waterfront Autumn Escape in Wine Country: 2BR

A sunlit living area features a light-colored sofa accented with blue pillows. A coffee table sits in front, and a ceiling fan adds comfort. Large windows provide views of greenery outside, while a side table with a lamp enhances the cozy ambiance.

Guesthouse in South End

4.88 out of 5 average rating, 69 reviews

Southold- Adorable 1 Bedroom Cottage

Other great vacation rentals in Greenport

Top guest favorite

A stylish living area showcases a comfortable sofa and accent chairs arranged around a modern coffee table. Warm wood flooring complements the dark walls, and soft lighting is provided by a chandelier. Large windows are dressed with elegant drapes, inviting natural light into the space.

Home in North Fork

5 out of 5 average rating, 30 reviews

Elegant Greenport Victorian -Winter Harbor House-

A spacious bedroom is illuminated by natural light from two windows. The queen bed is dressed in white linens with soft pink accent pillows. A small bedside table holds a lamp, while a dresser stands against one wall. A cozy chair is placed in the corner.

Guest suite in North Fork

4.97 out of 5 average rating, 98 reviews

Private Suite in a Greenport Historical Townhouse

The exterior of a meticulously restored Victorian house is showcased, featuring a light grey façade with white trim and a welcoming front porch. A decorative railing borders the yard, which includes neatly maintained landscaping, and the entrance is highlighted by a brown front door.

Apartment in North Fork

4.99 out of 5 average rating, 73 reviews

Victorian Pearl

Top guest favorite

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 North Fork

4.98 out of 5 average rating, 54 reviews

The Crow's Nest

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 North Fork

4.89 out of 5 average rating, 70 reviews

Year-Round Heated Pool Villa - 3 blocks from town

The sleeping area features a plush bed with white bedding and two neatly arranged pillows. Warm light from the wall-mounted lamps illuminates the space, while green foliage is visible through the large windows on either side, creating a soothing atmosphere.

Apartment in The Hamptons

4.96 out of 5 average rating, 27 reviews

The Hideaway | Clearwater Beach

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 North Fork

4.96 out of 5 average rating, 56 reviews

modern 3 bedroom home with fireplace

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 South End

4.79 out of 5 average rating, 66 reviews

Incredible 2 Bedroom Waterfront Cottage!

Quick stats about vacation rentals in Greenport

Total rentals
180 properties
Nightly prices starting at
R2,244 ZAR before taxes and fees
Total number of reviews
10K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Greenport?
Yes! Work meets play with ease at over 90 vacation rentals in Greenport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Greenport?
Four-legged friends are welcome in Greenport. Choose from more than 50 vacation rentals for guests traveling with pets.
How much does it cost to stay in boutique hotel rentals in Greenport?
Experience the best of Greenport with our boutique hotel rentals, starting at about $350 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Greenport vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Greenport, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Greenport have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Greenport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenport have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Greenport. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Greenport?
Greenport has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Greenport?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with self check-in, over 50 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore