Long Island Vacations from $565

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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.
The McKernan Inn

The McKernan Inn

3 out of 5
Price was $717, price is now $565 per person
$565
per person
Mar 25 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) 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

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $756, price is now $565 per person
$565
per person
Apr 7 - Apr 14
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (356 reviews)
It was perfect everything u can need and want

Reviewed on Feb 14, 2026

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $1,062, price is now $801 per person
$801
per person
May 2 - May 6
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DAL) 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 Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was $1,157, price is now $885 per person
$885
per person
May 2 - May 6
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $1,316, price is now $1,028 per person
$1,028
per person
May 2 - May 6
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

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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
$77 nightly
The price is $85 total per night from Feb 19 to Feb 20
$85 total
Feb 19 - Feb 20
Total with taxes and fees
8/10 Very Good! (1,358 reviews)
Great staff. .. deal with me well .. thanks steven

Reviewed on Feb 12, 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $164 total per night from Feb 18 to Feb 19
$164 total
Feb 18 - Feb 19
Total with taxes and fees
9.2/10 Wonderful! (1,760 reviews)
Nice decor and amenities (pantry)

Reviewed on Feb 11, 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $128 total per night from Mar 1 to Mar 2
$128 total
Mar 1 - Mar 2
Total with taxes and fees
9.2/10 Wonderful! (1,162 reviews)
The staff is excellent - efficient, gracious and always available to manage whatever comes up for the guest.

Reviewed on Feb 2, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,371 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 $565 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.