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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 Mastic

4.88 out of 5 average rating, 99 reviews

Cozy home. Comfy living

The whole group will enjoy easy access to everything from this centrally located home. three comfortable bedroom and two bathrooms with a large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. Grace period of 15 mins after check is given after that fees will incur at the nightly rate.

Guest suite in Branford

4.9 out of 5 average rating, 100 reviews

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Home in North Fork

4.93 out of 5 average rating, 107 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Home in Westhampton Beach

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

Houseboat in North Fork

5 out of 5 average rating, 10 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Home in Hampton Bays

4.81 out of 5 average rating, 64 reviews

Hamptons Indulge: Beaches, Restaurants, Wineries.

Escape to our stunning year-round retreat in Hampton Bays' Red Creek area. With over an acre of lush land, our charming residence offers unparalleled serenity and tranquility just minutes from local bay, beaches, and wineries. Ideal for family fun, friend retreats, and exquisite dining in the Hamptons. For off-season activities, explore wineries, animal feeding farms, apple and pumpkin picking, breweries, and more. Book now for your dream getaway!

Home in Remsenburg-Speonk

5 out of 5 average rating, 40 reviews

5-Star Listing: Hamptons Oasis, Easy from NYC

Welcome to our coastal retreat. Minutes away from Westhampton Beach and a super-easy commute from NYC. Perfect for families or a group of close friends to get away from it all. A bright, spacious, recently renovated home with light-filled rooms, new floors, coastal decor. Ultrafast Wifi, Alexas, and a new kitchen with the latest appliances. Beautifully landscaped gardens, heated pool, 6-person salt water hot tub (in winter or summer)!

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Absolutely no animals as owner has severe allergy.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Home in North Fork

4.98 out of 5 average rating, 175 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.

Cottage in Shelter Island

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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

Hotels

Stylish accommodations and amenities

Popular amenities for Greenport vacation rentals

Laptop-friendly workspace

Stay near Greenport's top sights

Noah's103 locals recommend

Kontokosta Winery75 locals recommend

The Frisky Oyster75 locals recommend

Aldo's Coffee Company53 locals recommend

Little Creek Oyster Farm & Market53 locals recommend

American Beech52 locals recommend

Greenport apartment rentals

Apartment in North Fork

4.82 out of 5 average rating, 119 reviews

House on First

Apartment in Westhampton Beach

4.94 out of 5 average rating, 105 reviews

NEW, steps to the village 1 mile to Dune Road

Apartment in North Fork

4.96 out of 5 average rating, 142 reviews

Upscale Newly Constructed Apartment

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 245 reviews

Squire Chase House

Apartment in Southampton

4.87 out of 5 average rating, 127 reviews

Southampton Village Studio

Apartment in Sag Harbor

4.92 out of 5 average rating, 146 reviews

Whaling Captain Pierson's Apartment TOO

Apartment in North Fork

4.97 out of 5 average rating, 239 reviews

Greenport Village View - Walk Downtown 2BR/1BA

Apartment in Sag Harbor

4.89 out of 5 average rating, 154 reviews

Sag Harbor Village Oasis

Other great vacation rentals in Greenport

Cottage in North Fork

5 out of 5 average rating, 12 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Cottage in Guilford

4.99 out of 5 average rating, 128 reviews

"Red House on the Knoll" at Indian Cove

Home in Hampton Bays

4.9 out of 5 average rating, 92 reviews

Private Home minutes from Beach and Nightlife

Home in Sag Harbor

5 out of 5 average rating, 11 reviews

Delightful Sag Harbor Home w Pool

Home in Old Lyme

4.8 out of 5 average rating, 5 reviews

Beach Front Hawks Nest Beach (B)

Villa in Water Mill

4.96 out of 5 average rating, 28 reviews

Incredible 9+ Bedroom Watermill Home w Heated Pool

Home in North Fork

4.78 out of 5 average rating, 41 reviews

Farm house with vineyard views

Home in Old Saybrook

5 out of 5 average rating, 41 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

Quick stats about vacation rentals in Greenport

Total rentals
170 properties
Nightly prices starting at
R1,669 ZAR before taxes and fees
Total number of reviews
9.6K reviews
Family-friendly rentals
120 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 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 $200 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 20 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 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.

Destinations to explore