
Long Island Vacations from $448
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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 $585, price is now $448 per person
$448
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.2/10 Wonderful! (1,581 reviews)
Nice hotel within walking distance of everything downtown.
Reviewed on Oct 9, 2025

Cliff House Maine
Save 100% on your flight
Price was $1,160, price is now $810 per person
$810
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
The views were absolutely breath taking every where on the property. Staff extremely friendly and caring. Night time entertainment was a plus.
Reviewed on Oct 8, 2025

The Weldon Hotel
Downtown Portland
Price was $1,097, price is now $821 per person
$821
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (79 reviews)
Great spot, large space, cool design, clean, easy to walk all over town.
Reviewed on Oct 1, 2025


Inn By The Sea
Save 100% on your flight
Price was $1,268, price is now $982 per person
$982
per person
Nov 20 - Nov 23
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Portland (PWM)
9.4/10 Exceptional! (281 reviews)
Absolutely 5 star. Best bed I’ve slept in at a hotel bar none.
Reviewed on Sep 10, 2025
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Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,115 reviews)
"Fine for a night on our way to the outer parts of Maine"
Reviewed on Oct 6, 2025

Germaine Inn South Portland
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
7.4/10 Good! (288 reviews)
"It was convenient right off the highway. The room was clean and comfortable and the staff was friendly"
Reviewed on Oct 2, 2025

Fireside Inn & Suites Portland
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
7.8/10 Good! (1,013 reviews)
"A renovation would be good."
Reviewed on Oct 7, 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.
Long Island Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Population | 210 |
Max Temp Winter | 30ºF |
Max Temp Summer | 70ºF |
Top Sights | State Theatre, Higgins Beach and East End Beach |
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- Great Diamond Island Vacations
- Visit Great Diamond Island
- Peaks Island Vacations
- Visit Peaks Island
- Umbrella Cover Museum
- Mackworth Island
- East End Beach
- Spring Point Ledge Lighthouse
- Fort Preble
- Eastern Promenade
- Casco Bay Islands Vacations
- Bug Light
- Capt Lyman Stuart
- Gilsland Farm Audubon Center
- South Portland Historical Society Museum
- Southern Maine Community College
- Maine Narrow Gauge Railroad Company and Museum
- Portland Vacations
- Visit Casco Bay Islands
- Casco Bay Lines Ferry Terminal
- Visit Willard Beach
- Maine Jewish Museum
- Lyric Music Theater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.