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Greenport holiday lettings

We found 1,052 holiday rentals — enter your dates for availability

Discover a selection of 97 homes, 17 apartments and other holiday rentals in Greenport that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a TV. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Greenport

Showing deals for:9 Jan - 16 Jan

Image gallery for HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern

Pool
9.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern

Southold, NY

8% off
Price is £11,992
for 7 nights, 1 home
£1,713 per night
includes taxes & fees
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern

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Find out more about Greenport

Find out more about Greenport

Why visit Greenport

  • Scenic Beaches: Enjoy the picturesque beaches ideal for sunbathing and leisurely strolls along the shore.
  • Outdoor Adventures: Engage in various outdoor activities, from hiking to water sports, perfect for the adventurous spirit.
  • Historic Sites: Discover charming historic buildings and landmarks that reflect Greenport's rich heritage.
  • Family-Friendly Atmosphere: Explore numerous attractions suitable for families, ensuring a delightful experience for all ages.
  • Charming Local Vibe: Immerse yourself in the friendly local culture and enjoy the warm hospitality of the residents.

Popular types of accommodation in Greenport

Vrbo offers an array of accommodation options in Greenport, making it easy to find the perfect spot for your getaway. Whether you prefer a private vacation home, a charming cottage, or a convenient apartment, we have something to suit every traveller's needs. Popular choices include Greenport beach rentals and home rentals, ensuring you enjoy a relaxing stay by the coast. Discover the ideal Greenport vacation rental for your next adventure!

  • Houses: The top choice for visitors to Greenport, offering ample space and comfort for families or groups.
  • Cottages: A delightful option that provides a quaint and homely atmosphere, perfect for a relaxing getaway.
  • Apartments: Ideal for those seeking a self-catering experience, combining convenience and a central location.
  • Condos: A popular choice for those who enjoy modern amenities with a communal vibe.
  • Villas: Luxurious spaces that offer an upscale experience, perfect for indulgent holidays.**

Top attractions in and around Greenport

Greenport, New York, is an idyllic destination for outdoor and romantic beach holidays, offering a blend of culture and relaxation. Visitors can explore its beautiful beaches, urban parks, and historic buildings, making it perfect for those seeking both adventure and leisure. With friendly attractions and activities, Greenport promises a delightful experience for all types of travellers, whether you're here solo, with family, or as a couple.

  • 67 Steps Beach: A charming beach located within Greenport, 67 Steps Beach offers a relaxed atmosphere with stunning views of the water. Perfect for sunbathing and leisurely strolls, it encapsulates the quintessential beach vibes of the area.
  • Railroad Museum of Long Island: This museum showcases the rich railway history of Long Island, featuring vintage trains and impressive exhibits. Visitors can immerse themselves in the local culture and explore the fascinating stories of the region's railroads.
  • Gardiner's Bay Country Club: Situated 1.2km from Greenport, this scenic golf club offers a serene golfing experience. With beautifully maintained fairways and stunning views of Gardiner's Bay, it's ideal for both avid golfers and those looking to enjoy the outdoors.

Things to do recommended for couples

For a romantic getaway in Greenport, visit Kontokosta Winery for a delightful wine tasting experience, or venture 1.2km to Shelter Island Whale's Tail for some fun mini-golf. Don’t miss Pindar Vineyards, just 4.3km away, perfect for a charming afternoon together.

Things to do recommended for families

Families visiting Greenport can enjoy a delightful ride on the charming Greenport Carousel, unwind at Cedar Point County Park, and explore the serene Goldsmith's Inlet Park, both offering lovely spots for relaxation and wellness just a short distance away.

Things to do recommended for groups

In Greenport, groups can enjoy the vibrant Greenport Farmers' Market for local produce, catch a captivating performance at Bay Street Theatre for a bit of culture, and unwind with a round of golf at Island's End Golf & Country Club amidst beautiful outdoor settings.

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

When travelling with a group, family, pets, or seeking extended stays, it's essential to apply the right filters according to your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Greenport with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Greenport with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Greenport: For many, a family holiday wouldn't feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortably at home.
  • Planning for a long term stay visiting Greenport: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. 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, offers a delightful blend of outdoor adventures, romantic beach getaways, and family-friendly excursions. Visitors can immerse themselves in the charming local atmosphere, explore picturesque scenery, and enjoy the warmth of friendly locals. Whether you’re seeking summer fun along the coast or hidden gems in nearby areas, Greenport is the perfect base for an unforgettable holiday filled with memorable experiences and scenic delights.

  • Hamptons: The Hamptons, located 6.8km from Greenport, is a quintessential summer retreat known for its stunning beaches and vibrant outdoor lifestyle. This area offers a romantic atmosphere, making it perfect for couples seeking a getaway. Visitors can indulge in a variety of activities, from relaxing on picturesque family beaches to enjoying rounds of golf at scenic courses. The Hamptons also hosts lively music concerts and luxurious resorts, providing entertainment and relaxation in equal measure. With its charming seaside towns and beautiful landscapes, the Hamptons is a captivating destination for any traveller.
  • Shelter Island: Just 1.9km from Greenport, Shelter Island is a serene escape that boasts beautiful outdoor spaces and stunning beaches. This island is ideal for those looking for a romantic getaway or an adventure-filled trip. Popular activities include golfing, as well as exploring the island's ski fields during the winter months. Visitors can unwind on the family-friendly beaches or take part in various water activities on the lake. Shelter Island’s tranquil environment and natural beauty make it a delightful stop for relaxation and exploration.
  • Shelter Island Heights: Nestled only 621m from Greenport, Shelter Island Heights offers a charming mix of outdoor activities and romantic settings. The area is renowned for its golf courses and recreational areas, making it an excellent choice for sports enthusiasts. Guests can also enjoy the exclusivity of private country clubs. With its close proximity to beautiful beaches and the lake, Shelter Island Heights is perfect for leisurely strolls and picnics. This quaint locale promises a peaceful and picturesque retreat for visitors seeking a relaxing holiday.

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

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of accommodation.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new journeys, resume previous ones, or manage your travel arrangements with ease. You can easily access your saved or booked properties, which are neatly organised under Potential, Upcoming, or Current Trips. To begin utilising the Trip Boards, please visit: https://www.vrbo.com/en-gb/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 holiday 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 things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Greenport a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Kontokosta Winery (0.9 mi / 1.4 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)
  • Noyac Golf Club (8.3 mi / 13.4 km)
  • Peconic Bay Winery (8.6 mi / 13.8 km)

Exploring the natural landscape of Greenport

Whether you're looking for adventure or just want to spend some time taking in the scenery, Greenport is a great place to get out in nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • 67 Steps Beach (1.3 mi / 2.1 km)
  • Sunset Beach (2.1 mi / 3.3 km)
  • Crescent Beach (2.3 mi / 3.7 km)
  • Orient Point County Park (7.3 mi / 11.8 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 holiday, August, July, September and June are the hottest months to visit, when temperatures average 21°C.

Travelling to and around Greenport

The nearest airport is in East Hampton, NY (HTO), located 11.4 mi (18.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Fishers Island, NY (FID-Elizabeth Field), which is 20.1 mi (32.3 km) away.

If you'd rather travel by train, you can make your way to Greenport Station.

Frequently asked questions

What is the best area to stay in Greenport when booking a holiday rental?
When looking for the best area to stay in Greenport, New York, for a holiday rental, the historic downtown district is a fantastic choice. This charming area is brimming with character and features a lovely array of boutique shops, restaurants, and galleries, making it great for those who wish to immerse themselves in the local culture. You'll find an abundance of holiday rental properties here, with options ranging from quaint cottages to stylish apartments, suiting various preferences and budgets.

A short stroll from the downtown area leads you to the picturesque waterfront, where you can enjoy stunning views of the bay. One of the top attractions nearby is the Greenport Carousel, a beautifully restored hand-painted carousel that is a delight for both children and adults alike. Additionally, the nearby Mitchell Park offers a lovely green space to relax, complete with a playground and a charming marina, where you can watch the boats come and go.

Another appealing neighbourhood is the area surrounding the Greenport Harbor Brewing Co., ideal for those who enjoy craft beer and a lively atmosphere. This neighbourhood boasts several rental properties and puts you within easy reach of the brewery and its outdoor beer garden, great for summer evenings.
How much does it cost to rent a holiday home in Greenport?
Prices for holiday 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 holiday 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, travellers should consider the picturesque waterfront areas along Peconic Bay. The neighbourhoods near Greenport Village are particularly appealing, as they provide easy access to sandy beaches and charming local attractions. Many properties in this area feature amenities such as private decks, outdoor grills, and fully equipped kitchens, great for families or friends looking to enjoy a seaside getaway.

The beaches along the bay, such as the area near Founders Landing Park, offer opportunities for swimming, kayaking, and picnicking, making it an ideal spot for those who appreciate outdoor activities. Rentals here often come with additional comforts like air conditioning, Wi-Fi, and spacious living areas that encourage relaxation after a day spent on the beach.
What is the most popular type of holiday rental accomodation in Greenport?
In Greenport, holiday houses are the most popular type of rental, with approximately 86 available throughout the area. These properties are often situated near the waterfront and offer spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and outdoor spaces ideal for enjoying the serene surroundings. Many also feature amenities such as BBQ grills and decks or patios for al fresco dining, making them superb for families or groups looking to relax after a day of exploring local attractions like the charming shops and restaurants in the historic district.
Are there any family house rentals in Greenport?
In Greenport, New York, there are numerous family-friendly holiday rentals—about 78 available throughout the area. This charming town, located on the North Fork of Long Island, is superb for family getaways, offering a delightful mix of coastal beauty and local attractions. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor patios or gardens where children can play safely.
Can I rent a holiday home with a pool or hot tub in Greenport?
In Greenport, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 23 options to choose from. This charming village on Long Island's North Fork is known for its picturesque waterfront, local wineries, and vibrant arts scene. Many of the properties come with private pools and hot tubs, providing a superb spot for relaxation after a day of exploring the area. Find your rental in Greenport with a pool or a hot tub.
Can I find long-stay holiday rentals in Greenport?
A long-stay holiday rental in Greenport is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Greenport?
In Greenport, there are several pet-friendly house rentals available, providing a welcoming environment for travellers accompanied by their furry friends. Many of these holiday homes are equipped with thoughtful amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas, ensuring a pleasant stay. See all pet-friendly rentals in Greenport.
Are there any remote work holiday rentals in Greenport?
In Greenport, New York, there are plenty of remote work-friendly holiday rentals available, with around 106 options to choose from. This charming coastal town offers a variety of properties that cater to the needs of remote workers. Many rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable office chairs, making it easy to stay productive while enjoying a scenic getaway.

Travellers can expect properties that feature spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces for relaxing breaks. The picturesque surroundings provide a superb backdrop for unwinding after a busy workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greenport holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Greenport with parking available—perfect for families or travellers 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 rental amenities in holiday accommodations often include essential kitchen facilities such as a microwave, refrigerator, and dishwasher, enabling guests to prepare their own meals during their stay. Many rentals also provide cookware, dishware, and utensils, ensuring a fully equipped cooking experience. This makes it convenient for families and groups looking to enjoy local produce and flavours while relaxing in their home-away-from-home.
When is the best time to visit Greenport for a holiday rental?
The peak season for visiting Greenport is during the summer months, particularly from June to August, when the charming coastal village comes alive with visitors eager to savour the sun and explore its picturesque waterfront. July, in particular, is the most popular month, attracting families and adventure seekers who wish to enjoy the local beaches, wineries, and vibrant farmers' markets.

During this period, you can expect warm temperatures averaging around 25°C, making it superb for outdoor activities such as sailing, cycling, and leisurely strolls along the scenic boardwalk. The lively atmosphere is complemented by numerous events, including music festivals and art shows, providing ample opportunities to immerse yourself in the local culture.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to enjoy the serene beauty of Greenport as the autumn leaves create a stunning backdrop. You can take leisurely walks through the vineyards or explore the charming shops without the hustle and bustle of peak tourist crowds.
How early should I book a Greenport holiday rental?
Book your Greenport holiday 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 holiday 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, visitors can enjoy a charming seaside experience filled with unique attractions. The historic waterfront area is superb for leisurely strolls, offering picturesque views of the marina and the bustling activity of the fishing boats. Nearby, the Greenport Carousel, a beautifully restored antique carousel, provides a delightful experience for families and children.

Wine enthusiasts will appreciate the proximity to the North Fork wine region, with numerous vineyards and tasting rooms just a short drive away, where you can sample local wines and enjoy vineyard tours. The Long Island Maritime Museum offers insights into the area's nautical history and is worth a visit for those interested in maritime heritage.
Can I change or cancel my Greenport home rental booking on Vrbo?
To find Greenport holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Greenport holiday 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.

More holiday ideas

More holiday ideas