Long Island Vacations from $503

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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.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
per person
Sep 25 - Sep 28
found 10 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (793 reviews)
Staff extremely accommodating and friendly; very clean modern rooms; controllable ac

Reviewed on Jul 4, 2025

Nautical Mile

Nautical Mile

2.5 out of 5
Save 100% on your flight
per person
Aug 3 - Aug 8
found 15 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.4/10 Very Good! (12 reviews)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Sep 15 - Sep 19
found 9 hours ago
Roundtrip flight included
Minneapolis (MSP) to Portland (PWM)
9.4/10 Exceptional! (1,003 reviews)
There was no ambiance, back ground music in the restaurants or gathering areas. The towels were low grade. Wait staff was not consistent.

Reviewed on Jul 2, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (71 reviews)
Met our expectations

Reviewed on Sep 9, 2024

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (271 reviews)
It was one of the best getaways we have ever been on. Thank you for your hospitality.

Reviewed on Jun 13, 2025

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Long Island Hotel Deals

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
$116 nightly
The price is $127 total per night from Jul 6 to Jul 7
$127 total
Jul 6 - Jul 7
Total includes taxes and fees
7.8/10 Good! (1,002 reviews)
"Staff were great"

Reviewed on Jul 2, 2025

Days Inn by Wyndham Airport/Maine Mall
Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
Fully refundableReserve now, pay when you stay
$309 nightly
The price is $342 total per night from Jul 13 to Jul 14
$342 total
Jul 13 - Jul 14
Total includes taxes and fees
8.8/10 Excellent! (1,147 reviews)
just okay
"Well, no blanket or pillow for sleep sofa. Checked in no coffee available but clerk did make one from Starbucks was awful. VERY THIN walls could hear people coughing and going bathroom thru them. Not impressed for a Hyatt. only good thing was location."

Reviewed on Jul 2, 2025

Hyatt Place Portland Downtown - Old Port Square
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 Jul 7 to Jul 8
$168 total
Jul 7 - Jul 8
Total includes taxes and fees
7.8/10 Good! (1,011 reviews)
"This is my go to spot when I stay in Portland!"

Reviewed on Jul 1, 2025

Clarion Hotel Portland
See all 2,559 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 $503 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.