Long Island Vacations from $340

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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.
Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was $452, price is now $340 per person
$340
per person
Jan 23 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
19.2/10 Exceptional! (161 reviews)
Wish they had a liquor license and could do a cocktail hour in addition to a breakfast service. Wish they had just a tad more breakfast options. Really wish they had a key pad and front door access! LOVED the fire places in every room. Property manager was lovely and friendly. Loved the snacks available and variety.

Reviewed on Oct 27, 2025

Blind Tiger Portland – Carleton Street

Blind Tiger Portland – Carleton Street

3.5 out of 5
West End
Price was $584, price is now $456 per person
$456
per person
Jan 23 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
19.2/10 Exceptional! (119 reviews)
Adorable spot in Portland, great location, really cool concept. Felt like an upgraded vacation rental. You don’t have the whole place to yourself but it basically feels like it. Check in and everything was seamless. The local recommendations, games, and snacks were a nice touch. We loved plays scrabble and drinking wine in the parlor. We do wish some items were a bit nicer given the cost. The bathroom could've had nicer facilities (cheap toilet seat, low water pressure) our bed was a rickety. The breakfast delivered was a nice touch but the contents itself kinda fell flat, not as curated as the website made it seem. Overall we still enjoyed our stay and the concept, but the website may have upsold it a bit.

Reviewed on Nov 11, 2025

The Docent's Collection - Boyd Block

The Docent's Collection - Boyd Block

2 out of 5
Downtown Portland
Price was $526, price is now $416 per person
$416
per person
Jan 23 - Jan 25
found 6 hours ago
Roundtrip non-stop flight included
New York (LGA) to Portland (PWM)
20/10 Exceptional! (2 reviews)
Really nice and clean new hotel!

Reviewed on Oct 27, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,244, price is now $989 per person
$989
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Portland (PWM)
18.8/10 Exceptional! (1,001 reviews)
What an amazing experience! Definitely heading back there

Reviewed on Nov 18, 2025

The Kennebunk Inn

The Kennebunk Inn

2.5 out of 5
Price was $592, price is now $476 per person
$476
per person
Dec 26 - Dec 31
found 8 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
15.6/10 Exceptional! (745 reviews)
The room was very clean , the front staff was very helpful and sweet! Only thing that was a downside (but makes sense) due to the age of the building you can hear everything. If you are a light sleeper bring a fan to drown out some noise ! Hopefully will be back soon!

Reviewed on Nov 9, 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
$83 nightly
The price is $92 total per night from Nov 21 to Nov 22
$92 total
Nov 21 - Nov 22
Total with taxes and fees
7.8/10 Good! (1,231 reviews)
Room was clean.everything worked . Staff was helpful and friendly.

Reviewed on Nov 11, 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 Dec 7 to Dec 8
$98 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Clean room. Staff corrected a booking issue promptly.

Reviewed on Nov 9, 2025

The Westin Portland Harborview
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $157 total per night from Nov 23 to Nov 24
$157 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (1,676 reviews)
Excellent location, helpful front desk, quiet, clean, well-appointed room.

Reviewed on Nov 18, 2025

Portland Harbor Hotel
See all 2,372 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 $340 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.