Greenport vacation rentals

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Top-rated vacation rentals in Greenport

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Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Jan 8 – 15

G$155,277 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 85 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.

Feb 23 – Mar 2

G$90,008 GYD per night

Guest favorite

Condo in Greenport

4.91 out of 5 average rating, 107 reviews

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

Oct 8 – 15

G$65,834 GYD per night

Guest favorite

Apartment in Greenport

4.95 out of 5 average rating, 123 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. It is a week minimum during the peak season ( memorial day weekend until labor day weekend)

Dec 31 – Jan 7

G$89,909 GYD per night

Guest favorite

Guest suite in Greenport

4.92 out of 5 average rating, 276 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!

Aug 25 – Sep 1

G$70,566 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 165 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).

Mar 28 – Apr 4

G$39,078 GYD per night

Guest favorite

Home in Greenport

4.97 out of 5 average rating, 221 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!

Aug 18 – 25

G$119,526 GYD per night

Guest favorite

Townhouse in Greenport

4.96 out of 5 average rating, 100 reviews

Northfork Townhouse-walk to all/Newly Renovated

Fully Renovated Townhouse walking distance to town, beaches, parks, brewery and short bike to wineries. Brand new Kitchen, bathrooms & bedrooms. Enjoy all the North Fork has to offer: wineries, breweries, amazing restaurants, shops and beaches! 3 Bedrooms 1.5 bathrooms. We welcome you to come stay in our beautiful home and take in all the beauty of the North Fork. You can park your car and not have to drive again till you leave!

Jan 19 – 26

G$54,404 GYD per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 586 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!

Jul 7 – 12

G$47,966 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 143 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

May 7 – 14

G$159,946 GYD per night

Superhost

Apartment in Greenport

4.86 out of 5 average rating, 141 reviews

Quiet Neighborhood and only steps to Town

Walk the 5 min into town with restaurants and bars, shops and cafes or enjoy the quiet neighbourhood and take a stroll down the block to watch the sailboats cruise into Sterling Harbor. This sunny apartment is situated on the second floor of a 1860's house on one of Greenport's prettiest streets. Its the true couples getaway!

Dec 11 – 18

G$57,769 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 164 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.

Sep 4 – 11

G$119,351 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Greenport vacation rentals

Laptop-friendly workspace

Stay near Greenport's top sights

American Beech52 locals recommend

Claudio's Waterfront44 locals recommend

Lucharitos51 locals recommend

Claudio's39 locals recommend

Crazy Beans21 locals recommend

Noah's103 locals recommend

Other great vacation rentals in Greenport

Guest favorite

Condo in Greenport

4.93 out of 5 average rating, 124 reviews

Beautiful Waterview Condo on the North Fork of LI

Nov 29 – Dec 6

G$81,523 GYD per night

Superhost

Condo in Greenport

4.83 out of 5 average rating, 144 reviews

Sound front condominium

Jul 23 – 30

G$150,519 GYD per night

Guest favorite

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

Feb 14 – 21

G$99,006 GYD per night

Superhost

Condo in Greenport

4.89 out of 5 average rating, 80 reviews

Seaside Escape w Pool, Private Beach & Patio

Mar 16 – 23

G$121,612 GYD per night

Guest favorite

Condo in Sag Harbor

4.86 out of 5 average rating, 43 reviews

Cute cottage apartment upstairs above store in Sag

May 13 – 20

G$47,054 GYD per night

Superhost

Condo in Bridgehampton

4.92 out of 5 average rating, 13 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Nov 8 – 15

G$87,891 GYD per night

Superhost

Condo in New Haven

5.0 out of 5 average rating, 13 reviews

Private Studio | 10 min walk to Yale campus

Jun 29 – Jul 6

G$42,481 GYD per night

Guest favorite

Condo in Patchogue

4.83 out of 5 average rating, 59 reviews

Island Retreat in Historic Patchogue

Jan 15 – 22

G$53,393 GYD per night

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Other great vacation rentals in Greenport

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

Dec 24 – 31

G$116,895 GYD per night

Guest favorite

Apartment in Greenport

4.97 out of 5 average rating, 61 reviews

Lovely 2-bedroom apartment in a historic home

Sep 3 – 10

G$84,875 GYD per night

Guest favorite

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

Feb 23 – Mar 2

G$97,110 GYD per night

Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Oct 8 – 15

G$113,827 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

May 1 – 8

G$136,349 GYD per night

Guest favorite

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

Jan 27 – Feb 3

G$126,492 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 70 reviews

Beach House in L.I. Wine Country

Oct 24 – 31

G$99,720 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 19 reviews

The Corwin House

May 16 – 23

G$161,855 GYD per night

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Quick stats about vacation rentals in Greenport

Total rentals
160 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
8.1K reviews
Nightly prices starting at
G$20,848 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Greenport?
Yes! Work meets play with ease at over 80 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 house rentals in Greenport?
Experience the best of Greenport with our house rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 Greenport house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Greenport, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly apartment rentals in Greenport?
Greenport has more than 10 family-friendly apartment 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.

Greenport vacation rentals

Top-rated vacation rentals in Greenport

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Greenport vacation rentals

Stay near Greenport's top sights

Other great vacation rentals in Greenport

Condo in Greenport

Condo in Greenport

Condo in Greenport

Condo in Greenport

Condo in Sag Harbor

Condo in Bridgehampton

Condo in New Haven

Condo in Patchogue

Other great vacation rentals in Greenport

Home in Greenport

Apartment in Greenport

Home in Southold

Cottage in Greenport

Home in Greenport

Home in Greenport

Home in Greenport

Home in Greenport

Quick stats about vacation rentals in Greenport

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Greenport?

Are there pet-friendly vacation rentals in Greenport?

How much does it cost to stay in house rentals in Greenport?

Do house rentals in Greenport have self check-in?

Do house rentals in Greenport have a bbq area?

Are there Greenport house rentals on Airbnb with pools?

Are there family-friendly apartment rentals in Greenport?

What are the most popular amenities for House Rentals in Greenport?

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