Long Island Vacations from $645

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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.
Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Save 100% on your flight
Price was $977, price is now $645 per person
$645
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
7.6/10 Good! (1,050 reviews)
Great place to stay for AAU basketball in the area.

Reviewed on May 1, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,130, price is now $712 per person
$712
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

Meadowmere Resort

Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,586, price is now $1,008 per person
$1,008
per person
Jul 10 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Very well kept… great staff we had a great time

Reviewed on Apr 14, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,828, price is now $1,183 per person
$1,183
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,751 reviews)
We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.

Reviewed on Apr 29, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,880, price is now $1,271 per person
$1,271
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (300 reviews)
Super easy to find, the apartment was very clean, the complimentary water and coffee were excellent! We loved our stay!!

Reviewed on Apr 26, 2026

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Long Island Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $244 total per night from May 10 to May 11
$244 total
May 10 - May 11
Total with taxes and fees
9.4/10 Exceptional! (1,752 reviews)
Great location

Reviewed on May 2, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
$161 nightly
The price is $178 total per night from May 26 to May 27
$178 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,636 reviews)
The room was great. No microwave (which would have been helpful)

Reviewed on Apr 30, 2026

Portland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
$168 nightly
The price is $186 total per night from May 25 to May 26
$186 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,200 reviews)
First day my room wasn't cleaned ! Thought I'd get some complimentary water , but only had for first night !

Reviewed on May 1, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,455 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 $645 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.