Greenport vacation rentals

We found 1,026 vacation rentals — enter your dates for availability

Discover a selection of 98 homes, 16 apartments, and other vacation rentals in Greenport that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, such as air conditioning and a pool. At the end of the day, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Greenport

Showing deals for:Mar 6 - Mar 13

Image gallery for Lovely Cottage in the Heart of Long Island Wine country

Lovely pond front cottage on the North Fork.
9.8 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)

Lovely Cottage in the Heart of Long Island Wine country

Southold, NY

9% off
Price is $275
$1,928 for 7 nights
All fees included
Lovely Cottage in the Heart of Long Island Wine country

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Find out more about Greenport

Why visit Greenport

  • Scenic Beaches: Enjoy beautiful beaches perfect for sunbathing, swimming, and relaxation.
  • Charming Village: Explore the picturesque Greenport Village with its stunning landscapes and historic buildings.
  • Family-Friendly Activities: Engage in a variety of fun activities suitable for all ages.
  • Outdoor Adventures: Discover opportunities for hiking, biking, and water sports in the surrounding nature.
  • Cozy Accommodations: Choose from a range of vacation rentals, including charming cottages and private homes.

Popular types of accommodation in Greenport

Greenport offers a variety of vacation rentals to suit your needs, including houses, charming cottages, and cozy apartments. Whether you’re looking for house rentals, Airbnbs, or townhouse rentals, you’ll find plenty of options with great amenities. Choose the perfect accommodation for your getaway, and enjoy all that this picturesque destination has to offer.

  • Houses: The top choice for travelers in Greenport, these spacious homes offer the comforts of home, perfect for families or groups seeking a relaxing getaway.
  • Cottages: These charming, cozy retreats are ideal for those looking for a quaint and picturesque stay, often located near the waterfront.
  • Apartments: A convenient option for couples or solo travelers, these rentals provide all the essentials for a comfortable stay.
  • Condos: These modern accommodations offer amenities and often stunning views, blending luxury with accessibility.
  • Villas: For a more upscale experience, villas offer spacious living, beautiful surroundings, and a touch of elegance.**

Top attractions in and around Greenport

Greenport, New York, is the perfect destination for outdoor enthusiasts and romantic getaways, offering beautiful beaches, historic buildings, and urban parks. Whether you're seeking cultural experiences, family fun, or simply a relaxing day by the shore, there's something for everyone to enjoy. Explore the charming attractions within and around Greenport to create unforgettable memories during your vacation.

  • 67 Steps Beach: Experience the serene beach vibes at 67 Steps Beach, located in Greenport. With its picturesque views and sandy shores, it's the perfect spot for relaxation and enjoying the ocean breeze.
  • Orient Point County Park: Just 7 miles from Greenport, this urban park offers family-friendly outdoor activities, scenic trails, and picnic areas, making it an ideal destination for nature lovers and families alike.
  • Railroad Museum of Long Island: Immerse yourself in the rich culture of the region at the Railroad Museum of Long Island. Explore fascinating exhibits and learn about the history of railroads in New York.

Things to do recommended for couples

For a romantic getaway in Greenport, visit Kontokosta Winery for a charming wine tasting experience, or take a short trip to Raphael Winery for more delightful wines. Don't miss the fun at Shelter Island Whale's Tail mini-golf, perfect for friendly competition and laughter.

Things to do recommended for families

Families will have a blast at the Greenport Carousel, enjoying its charming outdoor setting. For a bit of relaxation, Cedar Point County Park and Goldsmith's Inlet Park, both located nearby, offer serene environments perfect for unwinding together in nature.

Things to do recommended for groups

In Greenport, groups can explore the vibrant Greenport Farmers' Market for local goods, enjoy a captivating performance at the Bay Street Theatre, or tee off at the scenic Island's End Golf & Country Club for a day of outdoor fun and relaxation.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Greenport

If you're planning a trip with friends, family, pets, or considering an extended stay, it's important to prioritize your preferences when searching. Here are some helpful booking tips for using Vrbo.

  • Traveling to Greenport with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Greenport with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Greenport: For many families, a vacation wouldn't feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Greenport: If you're in search of vacation rentals offering discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Greenport

Greenport, New York, is a charming coastal destination perfect for outdoor and romantic getaways. Explore the picturesque Greenport Village with its stunning natural landscapes, luxury homes, and family-friendly atmosphere. Enjoy excursions to nearby towns and relish the scenic views that capture the essence of this vibrant community. Whether you seek adventure or relaxation, Greenport offers a delightful blend of experiences for every traveler.

  • Hamptons: Located 11 miles from Greenport, the Hamptons are synonymous with luxurious beach getaways and vibrant summer living. This picturesque coastal area offers a blend of stunning beaches, upscale dining, and charming villages. Visitors can enjoy a romantic stroll along the pristine shores, indulge in fresh seafood at local restaurants, or partake in outdoor activities like golfing and boating. With its lively arts scene and music concerts, the Hamptons provide an unforgettable travel experience for couples, families, and outdoor enthusiasts alike.
  • Shelter Island Heights: Just 1 mile from Greenport, Shelter Island Heights is a tranquil retreat that captivates visitors with its scenic beauty and relaxed atmosphere. Known for its outdoor activities, this charming area features beautiful beaches, lush parks, and a welcoming community. Travelers can enjoy golfing at local courses or unwind at private country clubs. The proximity to serene lakes and family-friendly beaches makes it an ideal destination for romantic getaways or family vacations, offering a perfect balance of leisure and adventure.
  • Shelter Island: Located 3 miles from Greenport, Shelter Island is a hidden gem that boasts stunning natural landscapes and a laid-back vibe. This peaceful island is ideal for outdoor enthusiasts, offering ample opportunities for beach activities, hiking, and water sports. Visitors can explore local golf courses or enjoy unique winter sports like skiing at designated fields. With its inviting beaches and tranquil lakes, Shelter Island presents a romantic escape for couples and a delightful playground for families seeking adventure and relaxation.

Best time to go to Greenport

If you're planning a trip to Greenport, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyModerately LowModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyModerately HighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyModerately HighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyModerately HighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyAverageAverage
November49.6°F (9.8°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save some cash on your upcoming adventure? It might be helpful to stay flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your trip.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your reservation. It truly benefits you to take the lead. When you join our travel rewards program, One Key, you'll gain immediate access to member savings and have the opportunity to earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin your savings journey.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, just visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the natural landscape of Greenport

Enjoy the festivals and other features of Greenport. This city's beaches, island views and boating draw many visitors. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Greenport

Do you want to find attractions to see during your stay? Venture out of your vacation home and experience everything that makes Greenport a fun spot to vacation. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Kontokosta Winery (0.9 mi / 1.4 km)
  • The Old Field Vineyards (3.4 mi / 5.5 km)
  • Raphael Winery (7.1 mi / 11.4 km)
  • Pindar Vineyards (7.4 mi / 11.9 km)
  • Bedell Cellars (7.7 mi / 12.3 km)
  • Peconic Bay Winery (8.6 mi / 13.8 km)

Exploring the natural landscape of Greenport

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Greenport is a great spot to appreciate mother nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • 67 Steps Beach (1.3 mi / 2.1 km)
  • Sunset Beach (2.1 mi / 3.3 km)
  • Orient Point County Park (7.3 mi / 11.8 km)
  • Three Mile Harbor (10.5 mi / 17 km)
  • LongHouse Reserve (11.8 mi / 19 km)
  • Harvey's Beach (11.9 mi / 19.2 km)

Seasonal weather averages in Greenport

If you're hoping to enjoy some warm-weather activities on your vacation, August, July, September and June are the hottest months to visit, when temperatures average 70°F.

Traveling to and around Greenport

The nearest airport is in East Hampton, NY (HTO), located 11.4 mi (18.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Fishers Island, NY (FID-Elizabeth Field), which is 20.1 mi (32.3 km) away.

If you prefer train travel, the main station is Greenport Station.

Frequently asked questions

What is the best area to stay in Greenport when booking a vacation rental?
When planning a vacation rental in Greenport, New York, one of the best areas to consider is the historic downtown district. This charming neighborhood is known for its picturesque waterfront, quaint shops, and a vibrant dining scene. Staying here gives you easy access to popular attractions like the Greenport Harbor Brewing Co., where you can sample local craft beers, and the beautiful Mitchell Park, which features a playground, a carousel, and stunning views of the marina. The downtown area typically offers a variety of rental properties, ranging from cozy cottages to more upscale accommodations, allowing for a diverse selection to suit different tastes and budgets.

Another fantastic option is the area around Orient Point, which is just a short drive from Greenport. This tranquil neighborhood is known for its scenic beauty and proximity to the Orient Beach State Park, great for those who enjoy outdoor activities like hiking and picnicking. The nearby Orient Point Lighthouse adds a historic touch to the landscape, making it a lovely spot for photography.
How much does it cost to rent a vacation home in Greenport?
Prices for vacation rentals in Greenport vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Greenport to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Greenport vacation house rentals?
You can find great discounts on house rentals in Greenport on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Greenport?
For renting a beach house in Greenport, New York, the area around the waterfront offers some delightful options. The neighborhoods along the Long Island Sound, particularly near the Greenport Harbor, provide easy access to sandy beaches and scenic views of the water. Many vacation rentals in this area come equipped with amenities such as private docks, outdoor decks, and spacious living areas, ideal for families or groups looking to enjoy a seaside retreat.

The area near the historic Greenport Village is also a great choice, where travelers can find charming beach houses that often feature modern kitchens, outdoor grilling areas, and proximity to local shops and restaurants. This vibrant neighborhood is known for its lively waterfront and local attractions like the East End Seaport Museum, making it a convenient base for exploring the region.

Moreover, the nearby beaches, such as those at the end of Long Beach Road, offer picturesque spots for sunbathing and swimming. Rentals in this vicinity typically provide amenities like beachfront access, outdoor showers, and panoramic views, enhancing the beach experience for guests. Find your rental near the beach in Greenport.
What is the most popular type of vacation rental accomodation in Greenport?
In Greenport, vacation houses are the most popular type of rental, with around 92 available throughout the charming town. These houses typically offer spacious living areas, fully equipped kitchens, and outdoor spaces, ideal for enjoying the coastal atmosphere. Many are situated near local attractions such as the Greenport Harbor Brewing Co. and the historic Greenport Village, providing easy access to shops, restaurants, and waterfront views.

Additionally, there are about 14 apartments and 13 cottages for those seeking a cozier stay. The apartments often come with modern amenities and convenient locations near the town center, while the cottages provide a quaint, rustic experience, great for couples or small families.
Are there any family house rentals in Greenport?
In Greenport, New York, families will find a wealth of vacation rentals available, with around 86 options to choose from. The area is known for its charming coastal atmosphere and proximity to scenic attractions, making it an ideal spot for family getaways. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor patios where children can play and adults can relax.

Neighborhoods like the historic downtown area provide easy access to local shops, restaurants, and the beautiful waterfront, superb for leisurely strolls or enjoying a day by the water. Visitors can explore nearby highlights such as the Greenport Carousel and local wineries, which offer family-friendly experiences. With amenities like air conditioning, Wi-Fi, and sometimes even private gardens or pools, these rentals cater to the needs of families looking for comfort and convenience during their stay. See all family-friendly rentals in Greenport.
Can I rent a vacation home with a pool or hot tub in Greenport?
In Greenport, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 27 options to choose from. This charming seaside town on Long Island's North Fork offers a variety of properties, many of which are located near the waterfront and provide easy access to local beaches and attractions. Travelers can expect amenities such as private swimming pools, relaxing hot tubs, outdoor patios for al fresco dining, and fully equipped kitchens ideal for family meals. Find your rental in Greenport with a pool or a hot tub.
Can I find long-stay vacation rentals in Greenport?
A long-stay vacation rental in Greenport is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Greenport?
In Greenport, there are numerous pet-friendly house rentals available, with a variety of options to suit different preferences. Many of these rentals feature amenities such as spacious yards, outdoor seating areas, and fully equipped kitchens, making them ideal for families or groups traveling with pets. The charming coastal town offers a blend of modern comforts and rustic charm, with some properties showcasing beautiful views of the water.

The neighborhood itself is known for its welcoming atmosphere, and guests can enjoy easy access to various parks and dog-friendly spaces, ideal for pet owners. Nearby, the scenic Greenport Harbor provides opportunities for leisurely strolls along the waterfront, and there are pet-friendly restaurants and cafes where furry companions can join their owners. See all pet-friendly rentals in Greenport.
Are there any remote work vacation rentals in Greenport?
In Greenport, New York, there are plenty of remote work vacation rentals available, with around 112 options to choose from. This charming seaside community offers a variety of properties that cater to remote workers, featuring essential amenities such as Wi-Fi, dedicated office spaces with desks and chairs, and some even include additional conveniences like computer monitors and safes for personal belongings. Many rentals are situated close to the waterfront, providing a beautiful backdrop for work-life balance.

Travelers can enjoy the local attractions, including quaint shops, restaurants, and the scenic views of the Long Island Sound, all while having a comfortable and functional space to work from. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greenport vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Greenport with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Greenport?
In Greenport, popular vacation rental amenities include WiFi, which allows guests to stay connected during their stay, and fully equipped kitchens that provide the convenience of cooking meals at home. Many rentals also feature blenders for preparing smoothies or cocktails, as well as patios where guests can relax and enjoy the outdoors. Additionally, a coffee and tea maker is commonly available for those who appreciate a morning brew.
When is the best time to visit Greenport for a vacation rental?
The best time to visit Greenport for a vacation rental is during the vibrant summer months, particularly in July, when the area comes alive with energy and outdoor activities. This peak season, stretching from June to August, is great for travelers who enjoy warm weather and the charm of a coastal village. Visitors can bask in the sun on local beaches, explore charming boutiques, and take part in various water sports, all while soaking in the picturesque views of the Long Island Sound.

In July, temperatures typically range from the mid-60s to the low 80s Fahrenheit, creating a comfortable environment for those looking to engage in outdoor adventures or simply enjoy leisurely strolls along the waterfront. The lively atmosphere is complemented by numerous local festivals, farmers' markets, and culinary delights, making it an ideal time for food enthusiasts to savor the region's fresh seafood and local produce.

For those who prefer a more tranquil experience, November offers a unique opportunity to visit Greenport at a lower cost. While the summer crowds have dissipated, you can still enjoy the area's beauty, including crisp autumn air and stunning fall foliage.
How early should I book a Greenport vacation rental?
Book your Greenport vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Greenport?
In Greenport, travelers can enjoy a variety of attractions that showcase the charm of this historic maritime village. The waterfront area offers scenic views and is superb for leisurely strolls along the docks, where visitors can admire the fishing boats and yachts. The Greenport Harbor Brewing Co. is a popular spot for craft beer enthusiasts, providing a unique local experience.

The historic district features quaint shops and galleries, where travelers can explore local art and artisan goods. A visit to the East End Seaport Museum provides insight into the region's maritime history. Nearby, the picturesque Mitchell Park is a great place for families, featuring a playground, a pond, and a carousel.

For those interested in culinary experiences, Greenport offers a selection of seafood restaurants and farm-to-table eateries that highlight the area's fresh produce and catch.
Can I change or cancel my Greenport home rental booking on Vrbo?
To find Greenport vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Greenport vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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