Apartment vacation rentals in Greenport

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Top-rated apartment rentals in Greenport

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Superhost
A classic two-story house with a wooden exterior is framed by neatly trimmed greenery. The front porch features a white gate, inviting guests. Views of the water and trees are visible in the background, suggesting a serene location.
Apartment in The Hamptons
4.91 out of 5 average rating, 163 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Guest favorite
A charming two-story house is nestled among lush greenery, with large windows reflecting sunlight. The wooden exterior features shingle siding, and a gentle slope of grass leads up to the entrance. Surrounding trees create a serene, private atmosphere.
Apartment in The Hamptons
4.96 out of 5 average rating, 163 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Top guest favorite
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, 194 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 favorite
A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.
Apartment in South End
4.94 out of 5 average rating, 138 reviews

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

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
4.91 out of 5 average rating, 117 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.

Top guest favorite
A private kitchenette is displayed, featuring a wooden countertop, stainless steel refrigerator, and coffee maker. A small dining area with two wooden chairs and a round table is shown. Cozy seating is provided by a sofa adorned with decorative pillows. A doorway leads to the bathroom.
Apartment in Sag Harbor
4.95 out of 5 average rating, 179 reviews

Sag Harbor / Noyack Pad - private STUDIO apartment

500sq ft studio apartment, with private entrance, private bathroom, outdoor deck area with table/chairs, private kitchenette (but no stove). Close to Noyack Bay/Long Beach. 5 min drive to Sag Harbor village. 15 min to East Hampton village. 15 min to Ocean beaches. Responsive host: you will be greeted and handed keys when you arrive. No waiting around. Host will respond to all calls or messages rapidly if any issues arise. Lockbox entry with spare key also for 24 hour access

Guest favorite
An open living area features a comfortable gray sofa facing a flat-screen TV. A black coffee table sits on a textured rug, while a wooden dining table with chairs is positioned nearby. Sunlight filters through the blinds of the dual doors leading to the outside.
Apartment in North Fork
4.95 out of 5 average rating, 118 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.

Guest favorite
A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.
Apartment in North Fork
4.96 out of 5 average rating, 164 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

Top guest favorite
A sandy path leads through beach grass, flanked by wooden fencing, toward a tranquil ocean beyond. Clear blue skies complement the scene, where gentle waves are visible on the horizon.
Apartment in The Hamptons
4.98 out of 5 average rating, 130 reviews

Walk to Bay and Ocean-Newly Renovated

Newly renovated! Walking distance to beautiful bays , ocean beaches, restaurants and bars. Perfect Hamptons vacation getaway. Wine Country and Montauk are great day trips from this centrally located spot. Easily access Hampton Bays with public transportation via LIRR or Hampton Jitney, than a 3-5 minute Uber to apartment. Monthly stays will have cleaning service provided every two weeks.

Top guest favorite
The living area features a high ceiling with large windows, allowing natural light to brighten the space. A comfortable sofa adorned with colorful pillows sits opposite two red armchairs. A wooden coffee table holds various books and a decorative tray, creating an inviting gathering spot.
Apartment in Branford
4.97 out of 5 average rating, 109 reviews

Ridgeview Suite at Stony Creek Depot

The New England-chic interior design of the 1,300-sf Ridgeview Suite blends modern amenities with charming, unique vintage artifacts. With a large bright kitchen, office/library, wet-bar and laundry room, this 2-bedroom suite is ideal for families or corporate guests. Savor small town life in Stony Creek Village with its small public beach, playground, and sandwiches shops in town.

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, 112 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!

Superhost
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.
Apartment in Shelter Island Heights
4.9 out of 5 average rating, 259 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

Popular amenities for Greenport apartment rentals

Quick stats about apartment rentals in Greenport

  • Total rentals

    20 properties

  • Nightly prices starting at

    € 162 before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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