Long Island Vacations from $635

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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 $801, price is now $635 per person
$635
per person
Mar 12 - Mar 16
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
The staff was extremely helpful and went out of their way to ensure our stay was exceptional. Greatly appreciated.

Reviewed on Dec 24, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $918, price is now $690 per person
$690
per person
Mar 12 - Mar 16
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
This was a great stay! Had everything we wanted. Location was excellent.

Reviewed on Dec 24, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $900, price is now $690 per person
$690
per person
Feb 1 - Feb 6
found 10 hours ago
Roundtrip flight included
New York (JFK) 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

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
Downtown Portland
Price was $825, price is now $652 per person
$652
per person
Mar 12 - Mar 16
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $820, price is now $657 per person
$657
per person
Mar 12 - Mar 16
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,512 reviews)
Everything, wonderful hotel. Can't wait to be back.

Reviewed on Dec 25, 2025

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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
$84 nightly
The price is $93 total per night from Dec 28 to Dec 29
$93 total
Dec 28 - Dec 29
Total with taxes and fees
7.8/10 Good! (1,293 reviews)
Great room. Courteous staff.

Reviewed on Dec 21, 2025

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Jan 11 to Jan 12
$98 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Staff was so friendly and had great dining recommendations. Room was super clean. Hotel was quiet and located in a perfect spot around the corner from the comedy show we went to see. Everything was so nice and good luck to the ginger bread house decoration competitors! We hope our choice wins!

Reviewed on Dec 22, 2025

The Westin Portland Harborview
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
$149 nightly
The price is $165 total per night from Jan 4 to Jan 5
$165 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,553 reviews)
Very clean hotel, friendly staff, good food in the pub.

Reviewed on Dec 24, 2025

Portland Regency Hotel & Spa
See all 2,381 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 $635 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.