Long Island Vacations from $752

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

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

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $972, price is now $752 per person
$752
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Great location. You can walk famous restaurants and it’s pretty safe. The room was clean and the staff were very friendly.

Reviewed on Aug 25, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,546, price is now $1,026 per person
$1,026
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!

Reviewed on Aug 9, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $1,118, price is now $769 per person
$769
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.2/10 Wonderful! (52 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland

Reviewed on Aug 18, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,201, price is now $1,606 per person
$1,606
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.

Reviewed on Aug 25, 2025

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Save 100% on your flight
Price was $1,158, price is now $889 per person
$889
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (344 reviews)
Clean comfortable rooms. Nice amenities, walking distance to the beach and restaurants. Short drive or shuttle to downtown area. We would return and recommend this place.

Reviewed on Aug 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

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Sep 2 to Sep 3
$168 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,013 reviews)
"Nice sized room, good location, free bagels and muffins for breakfast."

Reviewed on Aug 25, 2025

Clarion Hotel Portland
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $117 total per night from Aug 27 to Aug 28
$117 total
Aug 27 - Aug 28
Total with taxes and fees
7.8/10 Good! (1,248 reviews)
"the breakfast was great"

Reviewed on Aug 25, 2025

Days Inn by Wyndham Airport/Maine Mall
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $141 total per night from Sep 2 to Sep 3
$141 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,050 reviews)
"Great"

Reviewed on Aug 24, 2025

Ramada Plaza by Wyndham Portland
See all 2,508 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.

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 $752 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.