Greenport Vacations from $767
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Your Greenport Vacation
Say farewell to planning hassles and hello to a Greenport vacation package. With your travel details organized before you leave, you can focus on discovering the best of this city, starting with Orient Point, which is great for views, fishing and nature. Fill up your itinerary with tours of 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery, some of the attractions you really should see during a trip to Greenport. Browse Expedia's extensive range of travel options and book your dream vacation to Greenport today.
The Latest Greenport vacation packages
Price found within the past 48 hours. Click for updated prices.
Radio Hotel
Manhattan
$767
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (2,455 reviews)
Some rooms do not have a/c. They said we would have a portable a/c in the room to help with the heat. We did not have one, we talked to the front desk and kept getting the run around. Finally on the last day we were there the manager moved us to a new room with a/c.
Reviewed on Sep 14, 2026
Stay near popular Greenport attractions
67 Steps Beach
9.6/10 (26 reviews)
Descend 67 wooden steps through lush greenery to reach this secluded Long Island Sound shoreline. Settle on natural boulder seats to witness spectacular sunsets over crystal-clear waters.
Kontokosta Winery
9.2/10 (48 reviews)
Long Island's only waterfront winery offers panoramic Sound views amid sustainable, wind-powered facilities. Savor award-winning wines in the modern tasting room or relax on the lawn overlooking vineyards.
Greenport Carousel
9.4/10 (50 reviews)
This 1920 Herschell-Spillman carousel features 36 hand-carved wooden horses in a harborside glass pavilion. Try your luck at the brass ring game—catch the golden ring for a free spin on this rare historic treasure.
Safe Harbor Stirling
This upscale North Fork marina offers pristine facilities and sheltered docking for vessels up to 80 feet. Enjoy the poolside cabanas before strolling to Greenport's historic village for exceptional dining.
East End Seaport Maritime Museum
9.0/10 (9 reviews)
This maritime museum showcases Long Island's seafaring heritage with historic Fresnel lenses and lighthouse exhibits. Explore their saltwater aquarium or visit during September's vibrant Maritime Festival.
Railroad Museum of Long Island
9.0/10 (7 reviews)
Housed in an 1892 freight house, this museum showcases the Long Island Rail Road's pivotal role in regional development. View vintage artifacts and model train layouts while exploring transportation heritage.
Greenport Harbor Brewing Company
This North Fork craft brewery transforms local flavors into distinctive beers in a historic firehouse. Sample specialties like Haus Pilsner while enjoying the art-filled space that captures Long Island's maritime spirit.
Camera Obscura
9.0/10 (11 reviews)
This rare optical device projects live, panoramic views of Greenport Harbor onto a viewing table in a darkened room. Experience a 360-degree perspective of the surroundings through its rotating mirror system.
What to do in Greenport
Greenport Hotel Deals
Sound View Greenport
58775 County Rd 48 Greenport NY
$245 nightly
$280 total
Oct 1 - Oct 2
Total with taxes and fees
8.4/10 Very Good! (723 reviews)
"The rooms were exceptionally clean, and the staff was friendly, attentive, and professional throughout our stay. However, the breakfast options were average and could definitely be improved. Overall, it was a pleasant experience, and I would still highly recommend this hotel."
Reviewed on Sep 14, 2026
Zey Hotel
439 Main Street Greenport NY
$169 nightly
$193 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (401 reviews)
"Such an amazing hotel to stay for the weekend"
Reviewed on Sep 9, 2026
North Fork Resort
690 Queen St Greenport NY
$278 nightly
$318 total
Sep 16 - Sep 17
Total with taxes and fees
9.6/10 Exceptional! (54 reviews)
"This property is so awesome! Adorable cottages, not very big, but sufficient. We were 2 couples, and we managed. Very quaint an comfortable. Services were provided if asked. They give you everything you need. I may buy in or for sure go back as a guest next year. We loved it, and it's so convenient ..."
Reviewed on Sep 9, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Greenport Vacation Packages
Greenport Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,200 |
Max Temp Winter | 40ºF |
Max Temp Summer | 75ºF |
Top Sights | Wolffer Estates Vineyard, 67 Steps Beach and Kontokosta Winery |
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Frequently asked questions
How much does a Greenport vacation package cost?
You'll find cheap prices from $767 on Expedia for your Greenport getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Greenport costs.
What are the cheapest months to go to Greenport?
September, November and December are great times to look for cheap Greenport vacation packages. Choosing to travel in less busy months means you'll typically find reduced prices on accommodations and flights.
How many days is enough for Greenport?
Greenport vacations come in various shapes and sizes, but to really sink your teeth into this destination, we reckon 2 days is about right. With this timeframe, you can visit top attractions like Railroad Museum of Long Island and East End Seaport Maritime Museum and seek out some underrated gems. Don't miss out on cool areas such as Greenport West and Pipes Cove either. If you're smart with your time, you can even schedule a day trip outside of Greenport too.
Is it worth booking a vacation package to Greenport?
Greenport is a good vacation destination with attractions like 67 Steps Beach among the many things to keep you busy. Whether you're traveling with the family or getting away with friends, a Greenport vacation promises a good time for everyone.
How to find the best Greenport package deals?
Finding a cheap Greenport package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Greenport package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Greenport vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Greenport vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Greenport?
If you're planning an impromptu Greenport vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Greenport?
- Pick your dates: What you'd like to do in Greenport and your preferred season can help you decide when to go.
- Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your hotel will probably be the biggest expense during your trip to Greenport.
- Explore Greenport using our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Greenport. You can also save your favorite places, collaborate with friends and family and manage your plans in one place.
- Set the duration of your trip: Start by making a list of all the activities and attractions you want to get to in Greenport. Then, estimate how long you'll need at each, along with any travel time.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Greenport vacation package that brings all your bookings together.
- Add on experiences and excursions: Have a look at our dedicated travel guide to find some awesome things to do in Greenport in Greenport. Book tickets or make reservations as soon as you can to save time and skip the hassle of looking for activities when you arrive.
Does Expedia offer Book Now, Pay Later Greenport vacation packages?
Your Greenport trip should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
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- Southold Vacations
- The Old Field Vineyards
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- Kontokosta Winery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.