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.
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
The Cliff House is a one of a kind! Always a fantastic visit!

Reviewed on Aug. 1, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
We were pleased with the neighborhood and our actual room. The staff member who checked us in seemed intoxicated and smelled strongly of alcohol. We were told we had a credit to use in the hotel but were charged and never received the credit. The room was very clean and the bed was comfortable. We enjoyed the historic neighborhood.

Reviewed on Aug. 4, 2025

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,009 reviews)
Great location and nice rooms.

Reviewed on Aug. 4, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
per person
Sep 15 - Sep 20
found 20 hours ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
9.6/10 Exceptional! (274 reviews)
It was one of the best getaways we have ever been on. Thank you for your hospitality.

Reviewed on Jun. 13, 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 $165 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,110 reviews)
"I enjoyed my stay and thought was excellent value for the money. For old property it has been kept up well. I enjoyed they had pool and strong AC in the rooms."

Reviewed on Aug. 3, 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 $148 per night from Aug 11 to Aug 12
CA $148
CA $161 total
Aug 11 - Aug 12
includes taxes & fees
7.4/10 Good! (111 reviews)
"Great place to stay"

Reviewed on Aug. 1, 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 $182 per night from Sep 1 to Sep 2
CA $182
CA $201 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,044 reviews)
"Great option to explore Portland."

Reviewed on Aug. 3, 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Long Island vacation package cost?
You'll find cheap prices from CA $1,326 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.