Greenport Vacation Packages

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,179, price is now CA $697 per person
CA $697
per person
Oct 6 - Oct 9
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Very large room, well maintained hotel, friendly helpful staff.

Reviewed on Aug. 25, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Price was CA $1,412, price is now CA $818 per person
CA $818
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (10 reviews)
Nice stay. Very low bed and little room to get in and out. Great location. If booking through Expedia, be careful to check for shared/private bathroom as the description is misleading.

Reviewed on Aug. 22, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Price was CA $2,637, price is now CA $1,541 per person
CA $1,541
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,083 reviews)
Excellent location and great staff

Reviewed on Aug. 26, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $2,508, price is now CA $1,476 per person
CA $1,476
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (1,293 reviews)
Great people, great place, rooms are spot on and Rooftop is worth every penny

Reviewed on Aug. 26, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Price was CA $1,940, price is now CA $1,145 per person
CA $1,145
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (870 reviews)
BEST – The hotel is very close to the Flatiron, with several subway lines reachable within a 5-minute walk. It’s clean, and the room is fine if you just need a place to shower and sleep. The front desk is available 24/7. WORST – Unfortunately, our room (707) was right next to a technical room, so we could hear mechanical noises day and night. We also asked for the TV to be fixed, but it was never taken care of.

Reviewed on Aug. 26, 2025

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 $365 per night from Sep 14 to Sep 15
CA $365
CA $484 total
Sep 14 - Sep 15
includes taxes & fees
8.4/10 Very Good! (562 reviews)
"Our luxury 2 bedroom suite was very nice, clean, and spacious. We had a huge balcony with a view of the Long Island sound"

Reviewed on Aug. 18, 2025

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 $274 per night from Sep 21 to Sep 22
CA $274
CA $381 total
Sep 21 - Sep 22
includes taxes & fees
8.6/10 Excellent! (508 reviews)
"Great location ,beautiful hotel,nice staff"

Reviewed on Aug. 25, 2025

The Harbor Front Inn
Greenporter Hotel

Greenporter Hotel

2 out of 5
326 Front St, Greenport, NY
The price is CA $176 per night from Sep 2 to Sep 3
CA $176
CA $202 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (185 reviews)
"The room was very comfortable"

Reviewed on Aug. 22, 2025

Greenporter Hotel
See all 4,218 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
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Discover the most popular places to visit in Greenport

Kontokosta Winery

You can enjoy a tasting or tour at Kontokosta Winery during your travels to Greenport West. Wander the beautiful beaches in this family-friendly area.

Kontokosta Winery

What to do in Greenport

Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $191
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Greenport

Frequently asked questions

How much does a Greenport vacation package cost?
You'll find cheap prices from CA $697 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.