
Long Island Vacations from $752
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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.
The Latest Long Island vacation packages
Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel
Downtown Portland
Price was $972, price is now $752 per person
$752
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.2/10 Wonderful! (1,545 reviews)
Great location. You can walk famous restaurants and it’s pretty safe. The room was clean and the staff were very friendly.
Reviewed on Aug 25, 2025

Cliff House Maine
Save 100% on your flight
Price was $1,546, price is now $1,026 per person
$1,026
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!
Reviewed on Aug 9, 2025

The McKernan Inn
Price was $1,118, price is now $769 per person
$769
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.2/10 Wonderful! (52 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland
Reviewed on Aug 18, 2025

The Docent's Collection
Downtown Portland
Save 100% on your flight
Price was $2,201, price is now $1,606 per person
$1,606
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.
Reviewed on Aug 25, 2025

InnSeason Resorts The Falls at Ogunquit
Save 100% on your flight
Price was $1,158, price is now $889 per person
$889
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (344 reviews)
Clean comfortable rooms. Nice amenities, walking distance to the beach and restaurants. Short drive or shuttle to downtown area.
We would return and recommend this place.
Reviewed on Aug 16, 2025
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View all tripsLong Island Hotel Deals

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Sep 2 to Sep 3
$168 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,013 reviews)
"Nice sized room, good location, free bagels and muffins for breakfast."
Reviewed on Aug 25, 2025

Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $117 total per night from Aug 27 to Aug 28
$117 total
Aug 27 - Aug 28
Total with taxes and fees
7.8/10 Good! (1,248 reviews)
"the breakfast was great"
Reviewed on Aug 25, 2025

Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $141 total per night from Sep 2 to Sep 3
$141 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,050 reviews)
"Great"
Reviewed on Aug 24, 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.