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.
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,825, price is now CA $1,102 per person
CA $1,102
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8/10 Very good! (1,000 reviews)
The best part of this hotel is the proximity and the size of the room. Hotel staff really hands-off, no amenities. Hotel very out dated and kind of dingy looking.

Reviewed on Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,502, price is now CA $1,381 per person
CA $1,381
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was CA $2,262, price is now CA $1,386 per person
CA $1,386
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Clean and comfortable

Reviewed on Nov 2, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,809, price is now CA $3,009 per person
CA $3,009
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Ready to book your vacation to Greenport?

 

Choose your dates

Greenport Hotel Deals

Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is CA $191 per night from Nov 17 to Nov 18
CA $191
CA $218 total
Nov 17 - Nov 18
includes taxes & fees
Zey Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is CA $214 per night from Nov 23 to Nov 24
CA $214
CA $284 total
Nov 23 - Nov 24
includes taxes & fees
8.4/10 Very good! (766 reviews)
"Views from the rooms were pretty. The rooms need attention. You share a deck with all the rooms on your block. The heating/air system is very loud and disrupts sleep. Staff was nice."

Reviewed on Nov 5, 2026

Sound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is CA $194 per night from Nov 15 to Nov 16
CA $194
CA $262 total
Nov 15 - Nov 16
includes taxes & fees
The Harbor Front Inn
See all 4,110 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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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 $1,102 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.