Greenport Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.

Top Greenport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,617, price is now CA $1,017 per person
CA $1,017
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,805 reviews)

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,819, price is now CA $4,245 per person
CA $4,245
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (713 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was CA $3,937, price is now CA $2,500 per person
CA $2,500
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $4,919, price is now CA $3,202 per person
CA $3,202
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,370, price is now CA $1,545 per person
CA $1,545
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,536 reviews)

Ready to book your vacation to Greenport?

 

Choose your dates

Greenport Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is CA $228 per night from Nov 22 to Nov 23
CA $228
CA $301 total
Nov 22 - Nov 23
includes taxes & fees
Sound View Greenport
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is CA $215 per night from Nov 8 to Nov 9
CA $215
CA $245 total
Nov 8 - Nov 9
includes taxes & fees
9.2/10 Wonderful! (440 reviews)
"The stay was perfect. I can't think of a single thing to criticize. As an example, when we were checking out, we called the manager on his cell to alert him that a fire truck was flushing the street hydrants, and that we noticed that the water in the room was brown. We knew that the maintenance of ..."

Reviewed on Oct 27, 2026

Zey Hotel
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is CA $185 per night from Nov 18 to Nov 19
CA $185
CA $251 total
Nov 18 - Nov 19
includes taxes & fees
9/10 Wonderful! (668 reviews)
"The room was clean and the staff is always wonderful. Parking was a nightmare because of the festival which had nothing to do with the hotel. My only issue is the breakfast , I wish it had a little more so I don’t have to go down the street to get something to eat . Honestly it’s not even an issue ..."

Reviewed on Oct 19, 2026

The Harbor Front Inn
See all 4,189 properties in Greenport
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.
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Stay near popular Greenport attractions

67 Steps Beach

9.6/10 (26 reviews)
Why not spend a carefree afternoon at 67 Steps Beach during your travels in Greenport? Take in the festivals and sunsets in the area.
See properties

Frequently asked questions

How much does a Greenport vacation package cost?
You'll find cheap prices from CA $1,017 on Expedia for your Greenport getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Greenport costs.
What are the cheapest months to go to Greenport?
You can usually find lower rates and greater availability in January, February and November. Explore our cheap Greenport vacation packages and you could get some great off-season deals.
How many days is enough for Greenport?
Allow at least 2 days for your Greenport vacation to take in everything that makes this place special. Stroll around popular areas, including Greenport West and Pipes Cove. Then head to the major sights such as Sparkling Pointe and Truman's Beach. With a well-organized itinerary, you'll be kept busy with room for some me-time too. Want to travel outside of Greenport? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Greenport?
It's no wonder a Greenport vacation is on the must-do list of many travellers. Popular attractions like 67 Steps Beach are just the beginning of things to see and do here.
How to find the best Greenport package deals?
Bagging a cheap Greenport package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Greenport package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Greenport vacation as a package?
You can enjoy significant savings on your Greenport break by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Greenport?
If you have your Greenport vacation dates finalized, book as early as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Greenport?

  1. Pick your dates: What you want to do in Greenport and your favourite season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and experiences. Your hotel will likely be the largest expense during your trip to Greenport.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Greenport. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the perfect Greenport vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.