Long Island Vacations from $557

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.

The Latest Long Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
Price was $749, price is now $557 per person
$557
per person
Feb 24 - Mar 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.4/10 Very Good! (1,001 reviews)
Nice hotel and friendly staff

Reviewed on Dec 12, 2025

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $809, price is now $561 per person
$561
per person
Feb 24 - Mar 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (1,001 reviews)
Front end lady very rude. Long hair, didn’t get her name. Young gentleman very nice, solved a misunderstanding with great customer service.

Reviewed on Dec 4, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $841, price is now $594 per person
$594
per person
Feb 24 - Mar 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Lovely stay in a beautiful room, appreciated the upgrade. Easy walk to downtown activities.

Reviewed on Dec 12, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
Price was $791, price is now $587 per person
$587
per person
Feb 24 - Mar 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (1,002 reviews)
clean room, digital key wonderful, good breakfast selection, staff very accommodating. Pool water very, very cloudy (negative)

Reviewed on Dec 9, 2025

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
Price was $754, price is now $560 per person
$560
per person
Feb 24 - Mar 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,121 reviews)
Room was good, bed snd shower were decent. Property feels a wee bit dated. Staff were nice. Restaurant/bar on site. Airport shuttle! About a mile from jetport. Great overnight spot for early morning flight out.

Reviewed on Dec 8, 2025

Don't see what you're looking for?
See all available trips from Columbus to Long Island
View all trips

Long Island Hotel Deals

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $73 total per night from Jan 11 to Jan 12
$73 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.8/10 Excellent! (1,646 reviews)
The room was nice and the staff were very nice.

Reviewed on Dec 8, 2025

Tru by Hilton Portland Airport Area
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $160 total per night from Dec 16 to Dec 17
$160 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (1,709 reviews)
Amazing. Everything was great!

Reviewed on Dec 11, 2025

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $148 total per night from Dec 21 to Dec 22
$148 total
Dec 21 - Dec 22
Total with taxes and fees
9.4/10 Exceptional! (1,548 reviews)
Perfect location, great hospitality.

Reviewed on Dec 12, 2025

Portland Regency Hotel & Spa
See all 2,391 properties in Long Island
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.

Find the Best Long Island Vacation Packages

Long Island Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
210
Max Temp Winter
30ºF
Max Temp Summer
70ºF
Top Sights
State Theatre, Higgins Beach and East End Beach

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Long Island vacation package cost?
You'll find cheap prices from $557 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?
November, December and January are great times to search for cheap Long Island vacation packages. Choosing to travel in quieter periods means you can typically find reduced prices on hotels and flights.
How many days is enough for Long Island?
Generally, a handful of days is enough to explore the top attractions during your Long Island vacation. But if you'd like to have more time to rest or take day trips, think about extending your trip.
How to find the best Long Island package deals?
Use Expedia's filter tool to help you find some fabulous Long Island package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Long Island package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Long Island vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Long Island vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Long Island?
Score incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Long Island break.
Does Expedia offer Book Now, Pay Later Long Island vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Long Island vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

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