Long Island Vacations from $541

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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.
AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was $668, price is now $541 per person
$541
per person
Jan 15 - Jan 18
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (225 reviews)
Wonderful stay, will definitely return. Great breakfast and we loved bringing our dog. Storage solutions in the form of more shelving and drawers in bathroom/shower and in main room to allow full unpacking seems like an easy fix.

Reviewed on Nov 21, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $698, price is now $587 per person
$587
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $667, price is now $588 per person
$588
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (649 reviews)
Beautiful room and common areas. Peaceful and comfortable. We didn't want to leave.

Reviewed on Nov 30, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Price was $750, price is now $677 per person
$677
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
10/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $652, price is now $592 per person
$592
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

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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 7 to Dec 8
$93 total
Dec 7 - Dec 8
Total with taxes and fees
7.8/10 Good! (1,273 reviews)
The room was spotless and the staff were great. Has been updated over the past few years.

Reviewed on Dec 2, 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
$98 nightly
The price is $108 total per night from Dec 21 to Dec 22
$108 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
This is our favorite spot to stay when we go to State Theater. The harbor view room on the 14th floor was gorgeous. The bed is very comfortable and I love the shower with aromatherapy shampoo. The staff is very friendly and I always look forward to the breakfast.

Reviewed on Nov 30, 2025

The Westin Portland Harborview
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 14 to Dec 15
$81 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (1,650 reviews)
Clean room, comfortable bed and we love that we can access Netflix and HBO Max

Reviewed on Nov 29, 2025

Tru by Hilton Portland Airport Area
See all 2,375 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 $541 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.