Long Island Vacations from $663

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    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 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.
84 Main

84 Main

4 out of 5
Price was $884, price is now $663 per person
$663
per person
Mar 15 - Mar 21
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,216, price is now $862 per person
$862
per person
Apr 18 - Apr 25
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room was very clean, neat vibe, tons of space! Made coming back from

Reviewed on Jan 23, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,108, price is now $807 per person
$807
per person
Mar 15 - Mar 21
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

2.5 out of 5
Downtown Portland
Price was $942, price is now $730 per person
$730
per person
Apr 18 - Apr 25
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
8.8/10 Excellent! (1,002 reviews)
Housekeeping came in while we were still sleeping and wish there was other parking options. But otherwise we had a great stay.

Reviewed on Feb 1, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,884, price is now $1,466 per person
$1,466
per person
Mar 15 - Mar 21
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 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

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Feb 5 to Feb 6
$92 total
Feb 5 - Feb 6
Total with taxes and fees
8/10 Very Good! (1,336 reviews)
Everything was wonderful

Reviewed on Jan 31, 2026

Clarion Hotel Portland Airport ME
Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
Fully refundable
$78 nightly
The price is $85 total per night from Feb 4 to Feb 5
$85 total
Feb 4 - Feb 5
Total with taxes and fees
7.4/10 Good! (1,006 reviews)
Clean room, comfortable beds, pet friendly, and very professional and personable staff. Extended my stay for another night

Reviewed on Jan 30, 2026

Long Creek Hotel by IHG
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$141 nightly
The price is $156 total per night from Feb 9 to Feb 10
$156 total
Feb 9 - Feb 10
Total with taxes and fees
9.2/10 Wonderful! (1,745 reviews)
Room very clean. All staff professional and courteous

Reviewed on Jan 30, 2026

Portland Harbor Hotel
See all 2,359 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 $663 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.