Long Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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 $1,003
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
This hotel was very nice. Complimentary breakfast was a plus. The property was well maintained and the location was nice and quiet. Only issue was the bathroom fan was extremely loud. Definitely needs replacement. There was also a bad odor in the room. I thought it came from the rug. Hubby thought it was coming from the ac unit. We did not complain and the odor disappeared within 2 days… will definitely stay here again. Great value for the money.
Reviewed on Aug 28, 2026
Inn By The Sea
CA $1,713
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (328 reviews)
Lovely property. Very well maintained and taken care of. The option of pool or beach is a plus. Although we didn’t utilize the activities available each day.. it seemed very family friendly. Definitely will be back but hopefully reserve a bigger room or suite. Charming outdoor seating on the huge lawn but mostly in the sun. An indoor lobby with some comfy seating would be great.
Reviewed on Aug 13, 2026
Portland Regency Hotel & Spa
Downtown Portland
CA $1,550
per person
Oct 23 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.4/10 Exceptional! (1,756 reviews)
Unless they are booked solid. I ONLY stay at the regency over the last several years. Fourth floor roof deck suite market street side ftw! Cheers!
Reviewed on Aug 28, 2026
Portland Harbor Hotel
Downtown Portland
CA $1,559
per person
Oct 23 - Oct 26
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
9.2/10 Wonderful! (1,817 reviews)
For the price I would expect more amenities. The “free” food by the elevator was pretty sparse with a broken ice machine and coffee maker
Reviewed on Aug 29, 2026
Ready to book your vacation to Long Island?
Long Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $152
CA $169 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very good! (1,634 reviews)
"."
Reviewed on Aug 29, 2026
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $95
CA $103 total
Sep 28 - Sep 29
includes taxes & fees
7.2/10 Good! (742 reviews)
"Accommodations were ok"
Reviewed on Aug 29, 2026
Waves Oceanfront Resort
87 W Grand Ave Old Orchard Beach ME
CA $222
CA $242 total
Sep 13 - Sep 14
includes taxes & fees
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 $1,003 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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- Flights from Detroit (DTW) to Portland (PWM)
- Flights from Halifax (YHZ) to Portland (PWM)
- Flights from Calgary (YYC) to Portland (PWM)
- Flights from Montreal (YUL) to Portland (PWM)
- Flights to Great Diamond Island
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- Flights from Portland Intl. Jetport
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- Portland Museum of Art
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- Palace Playland
- Ogunquit Beach
- Marden's Surplus and Salvage
- Ll Bean Flagship Store
- Camp Ellis Beach
- Casco Vacations
- Durham Vacations
- Westbrook Vacations
- Poland Vacations
- Scarborough Vacations
- Bailey Island Vacations
- Old Orchard Beach Pier
- Higgins Beach
- Gooch's Beach
- Scarborough Beach State Park
- Portland Head Light
- Freeport Vacations
- Ocean Park Vacations
- Visit Old Orchard Beach
- Visit Portland
- Popham Beach State Park
- Aquaboggan Water Park
- Visit Ferry Village
- Seashore Trolley Museum
- Old Orchard Beach Vacations
- Visit Old Port
- Maine Mall
- South Portland Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.