Long Island Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
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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.
Admiral Peary Inn
Price was CA $1,146, price is now CA $1,046 per person
CA $1,046
per person
Apr 3 - Apr 6
found 9 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.2/10 Wonderful! (44 reviews)
Quaint bed-and-breakfast. Clean and comfortable. Would definitely stay again.
Reviewed on Dec 8, 2025
Long Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Feb 16 to Feb 17
CA $105
CA $117 total
Feb 16 - Feb 17
includes taxes & fees
8/10 Very Good! (1,343 reviews)
Entire staff was top notch.Thanks to Drew mgr and Mathew.Recommend this place highly
Reviewed on Feb 3, 2026
Long Creek Hotel by IHG
171 Philbrook Ave South Portland ME
Fully refundable
The price is CA $107 per night from Feb 10 to Feb 11
CA $107
CA $116 total
Feb 10 - Feb 11
includes taxes & fees
7.4/10 Good! (1,000 reviews)
Room was clean, bed was large and comfortable, staff was friendly. Sadly however, The pool and hot tub were closed.
Reviewed on Feb 2, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Feb 10 to Feb 11
CA $130
CA $197 total
Feb 10 - Feb 11
includes taxes & fees
9.2/10 Wonderful! (1,751 reviews)
Wonderful stay!
Reviewed on Feb 7, 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.
Explore a world of travel with Expedia
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- Hotels near Southern Maine Community College
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- Oceanfront Hotels in Willard Beach
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- Flights to Great Diamond Island
- Flights from Atlanta to Casco Bay Islands
- Flights from Boston to Casco Bay Islands
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- Aquaboggan Water Park
- Bailey Island Vacations
- Beech Ridge Motor Speedway
- Casco Bay Islands Vacations
- Visit Casco Bay Islands
- Cousins Island Vacations
- Desert of Maine
- Dunegrass Golf Club
- East End Beach
- Freeport Vacations
- Great Diamond Island Vacations
- Visit Great Diamond Island
- Great Island Vacations
- Higgins Beach
- Ll Bean Flagship Store
- Maine Mall
- Mclellan-Sweat Mansion
- Monkey Trunks Extreme Aerial Adventure Park
- Old Orchard Beach Pier
- Old Orchard Beach Vacations
- Palace Playland
- Pine Point Beach
- Portland Head Light
- Portland Museum of Art
- Portland Vacations
- Scarborough Beach State Park
- Scarborough Vacations
- Shaw Park
- South Portland Vacations
- State Theatre
- Westbrook Vacations
- Windham Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
