A coastal town with autumn foliage, a marina, and a bridge in the background.

Eastport Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • 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

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Eastport Vacation

Reserve a Eastport vacation package and get set to experience this interesting city the stress-free way. Think about staying in the neighborhood of North Fork, which is great for coastal beaches and walking. You'll want to do a little exploring during your trip to Eastport. Carve out some time for big-name attractions such as Smith Point County Park, Long Island Game Farm and Swan Lake Golf Club. A few clicks is all it takes to craft a tailor-made Eastport vacation on Expedia.

Top Eastport vacation deals

Price found within the past 48 hours. Click for updated prices.
  • The entrance to RIU Plaza with a glass facade, a revolving door, and a sign indicating its location in Manhattan Times Square.
    Jan 22 - Jan 24

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    2 nights
    4.0 star property
    9.2/10 - Wonderful (4,178 reviews)
    "The staff was extremely helpful with early checkin and was happy to hold our luggage before our room was ready and after check out so we could enjoy the city. The room was clean, and the complimentary waters were nice. The buffet breakfast was definitely worth the price. We had an amazing view and delicious meal."
    Reviewed November 11, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,077
    CA $616
    per traveller
    found 1 day ago
    Hotel Riu Plaza Manhattan Times Square
  • A historic building with ornate architectural details, multiple floors, and illuminated windows.
    Jan 22 - Jan 24

    The St. Regis New York + Flight

    Manhattan
    2 nights
    5.0 star property
    9.2/10 - Wonderful (295 reviews)
    "The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $2,690
    CA $1,323
    per traveller
    found 1 day ago
    The St. Regis New York
  • A rooftop terrace with outdoor seating, a city view, and a brick building.
    Jan 7 - Jan 10

    JW Marriott Essex House New York + Flight

    Manhattan
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,001 reviews)
    Roundtrip • Hamilton (YHM) - New York (JFK)
    YHM - EWR • 1 stop LGA - YHM • 1 stop
    CA $2,227
    CA $1,249
    per traveller
    found 1 day ago
    JW Marriott Essex House New York
  • A hotel room with a desk, chair, and a view of the cityscape through large windows.
    Dec 24 - Dec 28

    Eurostars The Chemists’ Club Hotel + Flight

    Manhattan
    4 nights
    4.0 star property
    9.4/10 - Exceptional (568 reviews)
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - EWR • Nonstop LGA - YYZ • Nonstop
    CA $3,120
    CA $1,773
    per traveller
    found 1 day ago
    Eurostars The Chemists’ Club Hotel
  • A modern building with large glass windows and a prominent RII sign.
    Jan 22 - Jan 24

    Hotel Riu Plaza New York Times Square + Flight

    Manhattan
    2 nights
    4.0 star property
    9.0/10 - Wonderful (3,453 reviews)
    "The staff was friendly, and helpful. Our room was clean, but very small. Being next to the elevator was not the best as you can hear everything. The location of the hotel is excellent. No parking on site, but there is a parking garage a couple blocks away."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - New York (JFK)
    YYZ - LGA • Nonstop LGA - YYZ • Nonstop
    CA $1,166
    CA $664
    per traveller
    found 1 day ago
    Hotel Riu Plaza New York Times Square

Eastport Hotel Deals

A Holiday Inn Express hotel with a stone facade, large windows, and a covered entrance.

Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG
2.5 star property
11.2 km from Eastport
8.8 out of 10, Excellent, (1,000 reviews)
The price is CA $181
CA $206 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Riverhead - Long Island by IHG
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.
See all properties in Eastport

Frequently Asked Questions

How much does an Eastport vacation package cost?

You'll find cheap prices from CA $616 on Expedia for your Eastport break. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Eastport costs.

What are the cheapest months to go to Eastport?

If you're looking to book a cheap Eastport vacation package, consider travelling in January, February and March. You'll usually find lower prices on hotels and airfares during these quieter months — perfect for a budget-friendly break.

How many days is enough for Eastport?

Typically, a handful of days is enough to check out the major sights during your Eastport vacation. However, if you want to have more time to relax or go on day trips, think about extending your itinerary.

How to find the best Eastport package deals?

Start your search for an Eastport package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Eastport package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Eastport adventure underway.

Is it cheaper to book an Eastport vacation as a package?

You can enjoy significant savings on your next Eastport escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.

When to book a vacation package to Eastport?

Score fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Eastport trip.

How to plan a trip to Eastport?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Eastport.
  2. Budget wisely: As well as the price of your stay, you should factor in other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Eastport.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you'd like to experience in Eastport. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find an Eastport vacation package that brings all your bookings together.

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