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Greenport vacation rentals

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Top-rated vacation rentals in Greenport

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

Jun 4 – 11

€ 837 per night

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 7 – 14

€ 319 per night

Apartment in Greenport

4.95 out of 5 average rating, 122 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)

Feb 22 – Mar 1

€ 426 per night

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!

Jun 1 – 8

€ 305 per night

Home in Greenport

4.96 out of 5 average rating, 302 reviews

The Sandpiper- Apt #1

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).

Dec 15 – 22

€ 145 per night

Condo in Greenport

4.93 out of 5 average rating, 124 reviews

Beautiful Waterview Condo on the North Fork of LI

Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

Jul 20 – 27

€ 768 per night

Home in Greenport

4.97 out of 5 average rating, 220 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 20 – 27

€ 555 per night

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 10 – 17

€ 270 per night

Guest suite in Cutchogue

4.88 out of 5 average rating, 584 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!

Oct 5 – 12

€ 169 per night

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.

Jul 24 – 31

€ 833 per night

Apartment in Greenport

4.86 out of 5 average rating, 141 reviews

Only Steps from Restaurants and Beach

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 26 – Jan 2

€ 310 per night

Home in Greenport

4.98 out of 5 average rating, 163 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

€ 559 per night

Vacation rentals for every style

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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

Greenport condo rentals

Condo in Greenport

4.83 out of 5 average rating, 100 reviews

Seaside Condo w Private Deck, Pool + Private Beach

Apr 30 – May 7

€ 373 per night

Condo in Greenport

5.0 out of 5 average rating, 90 reviews

"Breathtaking Waterfront Water's Edge view"

Dec 15 – 22

€ 482 per night

Condo in Sag Harbor

4.86 out of 5 average rating, 43 reviews

Cute cottage apartment upstairs above store in Sag

May 14 – 21

€ 228 per night

Condo in Bridgehampton

4.92 out of 5 average rating, 13 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Sep 18 – 25

€ 469 per night

Condo in Patchogue

4.86 out of 5 average rating, 57 reviews

Island Retreat in Historic Patchogue

Mar 14 – 21

€ 263 per night

Condo in Sag Harbor

4.95 out of 5 average rating, 19 reviews

Charming Sag Harbor Condo right in town/Main St!

May 20 – 27

€ 522 per night

Condo in New Haven

5.0 out of 5 average rating, 13 reviews

Private Studio | 10 min walk to Yale campus

Jun 15 – 22

€ 191 per night

Condo in New Haven

4.83 out of 5 average rating, 260 reviews

Stunning, Spacious, Spotless. Close to Yale.

Jul 9 – 16

€ 200 per night

Other great vacation rentals in Greenport

Home in Greenport

4.9 out of 5 average rating, 29 reviews

Lovely 1st floor of farmhouse, wineries/downtown

Oct 15 – 22

€ 287 per night

Apartment in Greenport

4.96 out of 5 average rating, 24 reviews

Vintage 1880 Victorian gem.

Oct 25 – Nov 1

€ 264 per night

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

Oct 28 – Nov 4

€ 548 per night

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Oct 12 – 19

€ 433 per night

Apartment in Greenport

4.97 out of 5 average rating, 61 reviews

Lovely 2-bedroom apartment in a historic home

May 10 – 17

€ 394 per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Mar 1 – 8

€ 639 per night

Home in Greenport

5.0 out of 5 average rating, 18 reviews

Walk to Beach or to Town …

Oct 23 – 30

€ 401 per night

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

Feb 8 – 15

€ 595 per night

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
€ 94 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 apartment rentals in Greenport?
Experience the best of Greenport with our apartment rentals, starting at about $100 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 40 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 40 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