Vacation rentals in Greenport West

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Top-rated vacation rentals in Greenport West

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Guest favorite

Home in North Fork

4.9 out of 5 average rating, 29 reviews

Lovely 1st floor of farmhouse, wineries/downtown

Lovely Victorian home with private entrance, porch, & brick patio. Floor to ceiling windows in light filled large bedroom with en suite bathroom. Cozy den has a beautiful bay window and a queen-size pull-out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, and new flat screen TV can be found in the unit. Fantastic restaurants, wineries, beaches are nearby. Enjoy all the North Fork as to offer!

Jan 18 – 25

$250 per night

Guest favorite

Condo in North Fork

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

$278 per night

Guest favorite

Apartment in North Fork

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)

Jan 31 – Feb 7

$375 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!

Feb 22 – Mar 1

$210 per night

Guest favorite

Home in North Fork

4.92 out of 5 average rating, 422 reviews

Blue Bay Dream - 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).

Jan 3 – 10

$105 per night

Guest favorite

Guest suite in Southold

4.94 out of 5 average rating, 97 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.

Mar 22 – 29

$135 per night

Guest favorite

Home in North Fork

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

$497 per night

Guest favorite

Townhouse in North Fork

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 13 – 20

$225 per night

Guest favorite

Home in North Fork

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

Enjoy this centrally-located historic home restored w/ modern conveniences. 1st FL includes sunny living room w/ comfortable seating and smart TV; full eat-in modern kitchen; mudroom and powder room. 2nd FL has two spacious bdrms each with full ensuite bathrooms. Short walk to LIRR, Shelter Island Ferry and Jitney stop, steps from vibrant Front and Main Street shops, restaurants and beach.

Oct 30 – Nov 6

$490 per night

Guest favorite

Home in North Fork

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.

Nov 13 – 20

$739 per night

Guest favorite

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 3 – 10

$243 per night

Guest favorite

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

$499 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Greenport West vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Greenport West's top sights

Lavender By the Bay56 locals recommend

Kontokosta Winery75 locals recommend

American Beech52 locals recommend

Claudio's Waterfront44 locals recommend

Lucharitos51 locals recommend

Claudio's39 locals recommend

Other great vacation rentals in Greenport West

Guest favorite

Apartment in North Fork

4.95 out of 5 average rating, 74 reviews

Junior 1-BR in the heart of Greenport Village

Oct 20 – 27

$318 per night

Guest favorite

Apartment in Greenport

4.95 out of 5 average rating, 19 reviews

Farmhouse vibe in heart of Greenport

Feb 4 – 11

$415 per night

Guest favorite

Home in North Fork

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Oct 20 – 27

$570 per night

Guest favorite

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

Dec 30 – Jan 6

$529 per night

Superhost

Cottage in Greenport

4.84 out of 5 average rating, 38 reviews

Newly Renovated 2-Bedroom Home on the LI Sound

Aug 3 – 10

$808 per night

Guest favorite

Home in Greenport

4.96 out of 5 average rating, 25 reviews

Water front 3 bedrooms 2 bathrooms beach house

Nov 17 – 24

$669 per night

Guest favorite

Home in North Fork

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Nov 5 – 12

$376 per night

Guest favorite

Apartment in North Fork

4.96 out of 5 average rating, 47 reviews

Newly Renovated 2-BR Apartment

Dec 2 – 9

$325 per night

Show all

Quick stats about vacation rentals in Greenport West

Total rentals
280 properties
Rentals with a pool
70 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
210 properties are a good fit for families
Total number of reviews
11K reviews
Nightly prices starting at
$100 before taxes and fees

Frequently Asked Questions

Are there family-friendly vacation rentals in Greenport West?
Greenport West has more than 210 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Greenport West vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 70 vacation homes with pools in Greenport West, available on Airbnb. Make a splash and soak up the sun in style!
Do boutique hotel rentals in Greenport West have wifi?
Absolutely! We offer over 10 boutique hotel rentals with wifi in Greenport West. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greenport West have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Greenport West. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Greenport West?
Four-legged friends are welcome in Greenport West. Choose from more than 70 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Greenport West?
Yes! Work meets play with ease at over 120 vacation rentals in Greenport West featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do condo rentals in Greenport West have free parking?
Absolutely! We offer over 20 condo rentals with free parking in Greenport West. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Greenport West have a kitchen?
Absolutely! We offer over 10 condo rentals with a kitchen in Greenport West. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Greenport West?
Enhance your stay in our House Rentals with the most popular amenities: over 140 homes with wifi, over 140 homes with free parking, over 150 homes with air conditioning, over 140 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in boutique hotel rentals in Greenport West?
Experience the best of Greenport West with our boutique hotel rentals, starting at about $200 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Greenport West

Top-rated vacation rentals in Greenport West

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Greenport West vacation rentals

Stay near Greenport West's top sights

Other great vacation rentals in Greenport West

Apartment in North Fork

Apartment in Greenport

Home in North Fork

Home in Greenport

Cottage in Greenport

Home in Greenport

Home in North Fork

Apartment in North Fork

Quick stats about vacation rentals in Greenport West

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 family-friendly vacation rentals in Greenport West?

Are there Greenport West vacation rentals on Airbnb with pools?

Do boutique hotel rentals in Greenport West have wifi?

Do apartment rentals in Greenport West have air conditioning?

Are there pet-friendly vacation rentals in Greenport West?

Are there vacation rentals with a dedicated workspace in Greenport West?

Do condo rentals in Greenport West have free parking?

Do condo rentals in Greenport West have a kitchen?

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

How much does it cost to stay in boutique hotel rentals in Greenport West?

Destinations to explore