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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.

The McKernan Inn
Price was $1,108, price is now $765 per person
$765
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9/10 Wonderful! (47 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland
Reviewed on Aug 18, 2025

Cliff House Maine
Save 100% on your flight
Price was $2,129, price is now $1,473 per person
$1,473
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,005 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

Inn By The Sea
Save 100% on your flight
Price was $1,522, price is now $1,145 per person
$1,145
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug 18, 2025


Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $1,403, price is now $1,069 per person
$1,069
per person
Sep 26 - Sep 29
found 17 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
The decor and private garden were nice, as was the self-service pantry on the 2nd floor. The destination fee was a little annoying on top of the proxy room rate, as the credit for the bar was not useful for one member of our party who does not drink. Very convenient to Old Port.
Reviewed on Aug 17, 2025
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Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $127 total per night from Aug 24 to Aug 25
$127 total
Aug 24 - Aug 25
Total includes taxes and fees
7.8/10 Good! (1,200 reviews)
"Best part of the stay was the free parking and EV charger on site,"
Reviewed on Aug 19, 2025

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 Aug 25 to Aug 26
$168 total
Aug 25 - Aug 26
Total includes taxes and fees
7.8/10 Good! (1,016 reviews)
"The hotel definitely needs a facelift but it was fine for a brief one night stay. The bed was comfortable. When the elevator got stuck on the 5th floor while we waited in the lobby, the front desk clerk was quick to walk up the 5 flights to address the situation."
Reviewed on Aug 17, 2025

Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $139 total per night from Sep 2 to Sep 3
$139 total
Sep 2 - Sep 3
Total includes taxes and fees
7.6/10 Good! (1,052 reviews)
Everyone was great
"Just what i needed"
Reviewed on Aug 18, 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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- Hotels near Willard Beach
- 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.