Long Island Holidays

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    Better together
    Save up to €185 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Long Island

The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is €125 per night from 11 May to 12 May
€125
includes taxes & fees
11 May - 12 May
8.8/10 Excellent! (1,001 reviews)
"Lovely hotel for those who wish to be removed from the hustle of the Old Port. Friendly, clean, new and upscale facility. This area of Portland is a bit gritty--not at all dangerous Bar at the top of the building is very good with wonderful views."

Reviewed on 22 Apr 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
The price is €198 per night from 28 Apr to 29 Apr
€198
includes taxes & fees
28 Apr - 29 Apr
9/10 Wonderful! (1,476 reviews)
"While the staff at the hotel is nice and attentive, the property needs a major renovation. Our “junior suite” felt old, one of the windows didn’t work and would not stay open, some plugs didn’t work, same as 2 of the lamps, the bathroom is dark and the furniture looks old and somewhat damaged. The ..."

Reviewed on 20 Apr 2025

Portland Harbor Hotel
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is €82 per night from 28 Apr to 29 Apr
€82
includes taxes & fees
28 Apr - 29 Apr
7.6/10 Good! (1,000 reviews)
"Great stay at clarion! Staff were very kind and friendly- room was comfy and large. The pool/hot tub area was nice too- especially on a cold day like when I was visiting"

Reviewed on 20 Apr 2025

Clarion Hotel Portland
See all 2,437 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.

Frequently asked questions

How much does a Long Island holiday package cost?
You’ll find cheap prices 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 holiday to Long Island costs.
What are the cheapest months to go to Long Island?
You can usually find lower prices and better availability in January, February and March. Take a look at our cheap Long Island holiday packages and you could score some great off-season discounts.
How many days is enough for Long Island?
Usually, a handful of days is enough to visit the major attractions during your Long Island holiday. But if you want to have some time to unwind or take day tours, think about extending your itinerary.
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 holiday package as early as possible.
Is it cheaper to book a Long Island holiday as a package?
Expedia holiday 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 holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Long Island?

  1. Pick your travel dates: What you’d like to do in Long Island and your preferred season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to flights and activities. Your accommodation will likely be the largest expense during your trip to Long Island.
  3. Decide how many days away: Start by listing all the activities and sights you’d like to experience in Long Island. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that’s left is to pick a Long Island holiday package that brings all your bookings together.

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