Long Island Vacations from $448

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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 $585, price is now $448 per person
$448
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.2/10 Wonderful! (1,581 reviews)
Nice hotel within walking distance of everything downtown.

Reviewed on Oct 9, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,160, price is now $810 per person
$810
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
The views were absolutely breath taking every where on the property. Staff extremely friendly and caring. Night time entertainment was a plus.

Reviewed on Oct 8, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,097, price is now $821 per person
$821
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (79 reviews)
Great spot, large space, cool design, clean, easy to walk all over town.

Reviewed on Oct 1, 2025

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $1,042, price is now $798 per person
$798
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (347 reviews)
Nice and convenient

Reviewed on Oct 3, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $1,268, price is now $982 per person
$982
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.4/10 Exceptional! (281 reviews)
Absolutely 5 star. Best bed I’ve slept in at a hotel bar none.

Reviewed on Sep 10, 2025

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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
7.8/10 Good! (1,115 reviews)
"Fine for a night on our way to the outer parts of Maine"

Reviewed on Oct 6, 2025

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Clarion Hotel Portland
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
7.4/10 Good! (288 reviews)
"It was convenient right off the highway. The room was clean and comfortable and the staff was friendly"

Reviewed on Oct 2, 2025

Get rates
Germaine Inn South Portland
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,013 reviews)
"A renovation would be good."

Reviewed on Oct 7, 2025

Get rates
Fireside Inn & Suites Portland
See all 2,401 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.

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

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Frequently asked questions

How much does a Long Island vacation package cost?
You'll find cheap prices from $448 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.