
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.



Portland Harbor Hotel
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
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
Long Island Hotel Deals

Days Inn by Wyndham Airport/Maine Mall
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

Germaine Inn South Portland
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

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