Long Island Vacations from $458

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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 $676, price is now $458 per person
$458
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Very clean, perfect location, staff was very friendly and helpful!

Reviewed on Dec 9, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $839, price is now $660 per person
$660
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $846, price is now $673 per person
$673
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The property is beautiful, the staff is kind, and the rooms are spacious and clean. It was great to have a safe place to park the car while having so many things to do within walking distance. Being able to grab a quick breakfast before heading out was great too! We loved our stay here!

Reviewed on Nov 23, 2025

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Downtown Portland
Price was $766, price is now $619 per person
$619
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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

Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
Downtown Portland
Price was $673, price is now $552 per person
$552
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,001 reviews)
Yes, it was wonderful.

Reviewed on Dec 5, 2025

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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
$74 nightly
The price is $81 total per night from Dec 21 to Dec 22
$81 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (1,639 reviews)
Clean room, friendly staff, good free breakfast!

Reviewed on Dec 6, 2025

Tru by Hilton Portland Airport Area
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$157 nightly
The price is $174 total per night from Dec 14 to Dec 15
$174 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (1,706 reviews)
Everything was great! However it would nivce if there was a microwave at the snack stations on each floor.

Reviewed on Dec 8, 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
$137 nightly
The price is $152 total per night from Dec 23 to Dec 24
$152 total
Dec 23 - Dec 24
Total with taxes and fees
9.4/10 Exceptional! (1,542 reviews)
Yes, excellent service and we really enjoyed our stay.

Reviewed on Dec 4, 2025

Portland Regency Hotel & Spa
See all 2,390 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

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Frequently asked questions

How much does a Long Island vacation package cost?
You'll find cheap prices from $458 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.

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