Long Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Long Island Vacation
An easy way to experience this vibrant city is with a custom-made Long Island vacation package. Stay in the neighborhood of Parkside, which is great for festivals, markets and walking or choose someplace else — our packages are all about you. Sand Beach, Fifth Maine Museum and Little Diamond Island are just some of the sights worth visiting during your trip to Long Island. Whoever you're going away with and whatever your bank balance, your dream Long Island vacation is just a few clicks away with Expedia.
Top Long Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Moody
CA $849
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
We checked in a bit early, and we were greeted with ice tea and a smile. A very nice group of folks working and the breakfast was better than expected. We would absolutely stay here again.
Reviewed on Aug 11, 2026
Admiral Peary Inn
CA $908
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.8/10 Excellent! (55 reviews)
Had a wonderful one night stay at this property. Everything was spotless and top notch. Even walked into the common kitchen area to find fresh baked cookies for the guests.
Reviewed on Aug 7, 2026
Inn By The Sea
CA $1,426
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (327 reviews)
(+)
Location
Dog Friendly
Food
Parking
Everything you would expect from a luxury hotel - it is pricy.
Nothing negative.
Reviewed on Aug 2, 2026
Ready to book your vacation to Long Island?
Long Island Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $129
CA $141 total
Sep 10 - Sep 11
includes taxes & fees
7.2/10 Good! (665 reviews)
"Check in was very poor, took way too long and the line was very long. Property outside was overgrown with weeds and not very well kept. Rooms were ok for a cheap place to stop while traveling."
Reviewed on Aug 11, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $134
CA $146 total
Aug 18 - Aug 19
includes taxes & fees
6.4/10 (1,044 reviews)
"The room had a horrible smell. The door didn’t lock. There were holes in the wall covered in spackling."
Reviewed on Aug 11, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $182
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very good! (1,624 reviews)
"It did the job for 3 nights. A little out dated, the mattress felt like a old school spring bed. Bathroom small and could have been updated. Positive: pricing, close to Thompson Point, and cheap Uber to downtown Portland"
Reviewed on Aug 10, 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.
Frequently asked questions
How much does a Long Island vacation package cost?
You'll find cheap prices from CA $849 on Expedia for your Long Island getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Long Island costs.
What are the cheapest months to go to Long Island?
January, February and March are great times to look for cheap Long Island vacation packages. Opting to travel in quieter periods means you can typically find reduced prices on accommodations and flights.
How many days is enough for Long Island?
With around 2 days, you'll have enough time to experience popular neighbourhoods like Downtown Portland and Old Port during your Long Island vacation. Make sure to also add East End Beach and Eastern Promenade to your must-see list. In the mood for more adventures? Consider exploring outside of Long Island on day trips and tours.
How to find the best Long Island package deals?
Landing a cheap Long Island package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Long Island package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Long Island vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights separately. Better still, you can personalize your Long Island getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Long Island?
If you're planning a spontaneous Long Island trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Long Island?
- Choose your dates: The things you plan to do in Long Island and your preferred season will help you decide when to travel.
- Set your budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Long Island. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a deluxe getaway.
- Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Long Island. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Long Island vacation package that brings all your bookings together.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
