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
Price was CA $3,663, price is now CA $2,616 per person
CA $2,616
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,762 reviews)
The New England decor was pleasant. The free snack station on each floor was great (fruit, yogurt, granola, pastries, trail mix bars, coffee, multiple tea flavors, cookies) are a nice edition. We avoided the destination/resort fee be having breakfast or cocktails each day. The outdoor fire pits were enjoyable
Reviewed on May 23, 2026
River View Resort
Price was CA $2,205, price is now CA $1,589 per person
CA $1,589
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (324 reviews)
Clean room. Space for everyone, pool was nice, staff was friendly. Perfect for our last minute ski trip.
Reviewed on Apr 12, 2026
The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $2,512, price is now CA $1,968 per person
CA $1,968
per person
Jun 27 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.6/10 Exceptional! (307 reviews)
Beautiful hotel, wonderful location. My only note is that the bed and pillows were not as comfortable as I would expect from this kind of boutique hotel. Standard size pillows only, no king size pillows and no lumbar pillows, and a fairly hard mattress with a thin pad. The night before my stay, I stayed in a converted motel for 25% of the Docent’s price that had far superior bedding.
Reviewed on May 20, 2026
The Weldon Hotel
Downtown Portland
Price was CA $3,084, price is now CA $2,499 per person
CA $2,499
per person
Jun 27 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
Long Island Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from May 26 to May 27
CA $256
CA $336 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,766 reviews)
"Awesome!"
Reviewed on May 24, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from May 26 to May 27
CA $206
CA $228 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,646 reviews)
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix ..."
Reviewed on May 20, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $247 per night from May 26 to May 27
CA $247
CA $311 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,219 reviews)
"Clean room, nice location. Wish the tv was a smart tv, and found the $25/room sort of annoying since the restaurant on property was understaffed. But overall we enjoyed it."
Reviewed on May 21, 2026
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.
