Long Island Vacations from $643
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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.
Nautical Mile
$643
per person
Oct 26 - Nov 1
found 8 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (24 reviews)
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.
Reviewed on Sep 8, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
$920
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
Other than being a little hard to find, this spot was wonderful and so much nicer than a hotel room! Great location.
Reviewed on Sep 18, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
$920
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
Staff was very very good and super quick to respond.. I really liked the location for my visit bc everything was easily walkable. Room was comfortable but a little interesting walking all the way across for bathroom. A few small glitches with electrical probably just bc it’s done recently renovated.
Reviewed on Sep 18, 2026
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Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
$110 nightly
$120 total
Oct 18 - Oct 19
Total with taxes and fees
8.4/10 Very Good! (3,003 reviews)
"The staff at the front desk checked us in and out efficiently but lacked the warmth and hospitality. The bathroom stall was also slippery. Almost fell. Need to put some kind of traction to prevent falls."
Reviewed on Sep 18, 2026
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$88 nightly
$96 total
Oct 18 - Oct 19
Total with taxes and fees
6.4/10 (1,133 reviews)
"It was barely acceptable. Tun looked dirty and the main door showed signs of damage. The door to connecting room could not be deadbolt locked. Two flimsy back up locks were able to be engaged."
Reviewed on Sep 18, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$108 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
8.2/10 Very Good! (1,700 reviews)
"There was an odor to the second floor hallways and my room. The bed was not very comfortable. It was very inexpensive, and the room was clean looking, but the smell was off putting."
Reviewed on Sep 18, 2026
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 $643 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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- Flights from Atlanta (ATL) to Portland (PWM)
- Flights from Raleigh (RDU) to Portland (PWM)
- Flights from New York (LGA) to Portland (PWM)
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- Victoria Mansion
- Visit Portland
- Maine College of Art
- East End Beach
- Mackworth Island State Park
- Merrill Auditorium
- Casco Bay Lines Ferry Terminal
- Goddard Mansion
- Visit Bailey Island
- Spring Point Ledge Lighthouse
- Ll Bean Flagship Store
- Wadsworth-Longfellow House
- Eastern Promenade
- Portland Head Light
- Southern Maine Community College
- Quarry Run Dog Park
- Two Lights State Park
- Fort Williams Park
- Higgins Beach
- Maine Jewish Museum
- South Portland Vacations
- State Theatre
- Umbrella Cover Museum
- Fort Preble
- Charles Q. Clapp House
- Visit Old Port
- Maine Sports Hall of Fame
- Peaks Island Vacations
- International Cryptozoology Museum
- Portland Museum of Art
- Downtown Portland Vacations
- Bug Light
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
