Long Island Vacations from $647

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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 $969, price is now $647 per person
$647
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
7.6/10 Good! (1,051 reviews)
The internet was not secure The room did not have room darkening drapes. Breakfast was good. TV not usefall no NBC,ABC,CBS channel and very few other channels to watch except old out of date programming.

Reviewed on May 11, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $1,578, price is now $951 per person
$951
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,003 reviews)
Very convenient and helpful staff.

Reviewed on May 10, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,973, price is now $1,219 per person
$1,219
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
Clean room , friendly Staff , Breakfast was great !!

Reviewed on May 13, 2026

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Save 100% on your flight
Price was $1,362, price is now $919 per person
$919
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (341 reviews)
IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back.

Reviewed on Oct 14, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,490, price is now $1,017 per person
$1,017
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Great hotel with great staff!

Reviewed on May 12, 2026

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Long Island Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$241 nightly
The price is $266 total per night from May 25 to May 26
$266 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,767 reviews)
Great hotel with great staff!

Reviewed on May 12, 2026

Portland Harbor Hotel
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
$166 nightly
The price is $183 total per night from May 27 to May 28
$183 total
May 27 - May 28
Total with taxes and fees
9.4/10 Exceptional! (1,651 reviews)
A hotel has control over cleanliness, upkeep, and service. This hotel ranks very poorly in service. Not a single smile from any staff at check-in, check-out, or requests. They advertise pickup from the airport is available but after a call before flight, after landing, and then 3 more calls after ...

Reviewed on May 12, 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
$177 nightly
The price is $196 total per night from May 26 to May 27
$196 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (1,214 reviews)
Very clean and modern design, spacious room and overall the place was very quiet and made for a good night's sleep. Convenient to have the garage attached to the hotel, you just have to have your ticket validated by the front desk, but allows you to come and go as you please for the parking fee.

Reviewed on May 12, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,477 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 $647 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.