Long Island Vacation Packages

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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.

Top Long Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,056 reviews)
Very pet friendly place!

Reviewed on Aug. 7, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Incredible views and very confortable rooms

Reviewed on Aug. 6, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
Great option in Old Port. Very convenient to dining, shopping and boat tours. You can walk to everything. Courtyard was lovely in the evening for cocktails around the firepit. Would definitely recommend!

Reviewed on Aug. 7, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Portland (PWM)
9.4/10 Exceptional! (598 reviews)
The breakfast each more was varied and delicious. There are bikes on the property which are great to ride around town

Reviewed on Jul. 29, 2025

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
per person
Sep 27 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (856 reviews)
We enjoyed our visit

Reviewed on Aug. 7, 2025

Ready to book your vacation to Long Island?

 

Choose your dates

Long Island Hotel Deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 24 to Aug 25
CA $151
CA $164 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,126 reviews)
Pleasantly surprised!
"After I booked the room, I started to read some of the reviews and instantly began to regret my decision. I didn’t have time to refund it so we took a chance. I’m glad we did! I’m not sure what all the fuss was about. I saw no bugs. I thoroughly checked. Albeit the room wasn’t immaculate. Housecleaning ..."

Reviewed on Aug. 6, 2025

Days Inn by Wyndham Airport/Maine Mall
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
The price is CA $147 per night from Aug 17 to Aug 18
CA $147
CA $160 total
Aug 17 - Aug 18
includes taxes & fees
7.4/10 Good! (117 reviews)
"They did not have my accessible room ready when I arrived at 3 pm. The WiFi setup was very clunky and only partial worked."

Reviewed on Aug. 2, 2025

Germaine Inn South Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Sep 1 to Sep 2
CA $181
CA $200 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,036 reviews)
"I thought it was clean and well maintained. The pool and hot tub were nice. The pillows were too small though and I would have liked a bigger comforter."

Reviewed on Aug. 4, 2025

Ramada Plaza by Wyndham Portland
See all 2,529 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.
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Frequently asked questions

How much does a Long Island vacation package cost?
You'll find cheap prices from CA $937 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?
January, February and March are great times to look for cheap Long Island vacation packages. Opting to travel in quieter periods means you can typically find reduced prices on accommodations and flights.
How many days is enough for Long Island?
With around 2 days, you'll have enough time to experience popular neighbourhoods like Downtown Portland and Old Port during your Long Island vacation. Make sure to also add East End Beach and Eastern Promenade to your must-see list. In the mood for more adventures? Consider exploring outside of Long Island on day trips and tours.
How to find the best Long Island package deals?
Landing a cheap Long Island package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Long Island package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Long Island vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights separately. Better still, you can personalize your Long Island getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Long Island?
If you're planning a spontaneous Long Island trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Long Island?

  1. Choose your dates: The things you plan to do in Long Island and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Long Island. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a deluxe getaway.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Long Island. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Long Island vacation 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.