Cliff Island Vacations from $534
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The Latest Cliff Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort
$534
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8.6/10 Excellent! (1,010 reviews)
Clean room, paid breakfast, front office staff very efficient, very limited items even in paid breakfast section.check in time 4 pm and check out 11 am.
Reviewed on Sep 2, 2026
The Wolfeboro Inn
$757
per person
Oct 24 - Oct 28
found 16 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
8.2/10 Very Good! (631 reviews)
Just returned from a several-day stay at the Wolfeboro Inn. It was absolutely delightful! Clearly an older establishment, but well-maintained and very clean, cozy, and comfortable. The staff was especially friendly and helpful. Very welcoming! Sweet location right on the lake & close to the lovely downtown - so pretty! Extra kudos also to the tavern…the food is excellent at great prices!
👏🤗👏
Reviewed on Sep 1, 2026
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View all tripsCliff Island Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$76 nightly
$82 total
Sep 10 - Sep 11
Total with taxes and fees
6.4/10 (1,109 reviews)
"."
Reviewed on Sep 3, 2026
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
$116 nightly
$127 total
Sep 10 - Sep 11
Total with taxes and fees
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
$68 nightly
$74 total
Sep 14 - Sep 15
Total with taxes and fees
7.2/10 Good! (768 reviews)
"This hotel was way above our expectations. The modern room and bathroom were very clean. The fridge came in handy as well as the coffee maker. Nice little breakfast lounge. We will stay there again next time we are near Portland, ME."
Reviewed on Sep 3, 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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Frequently asked questions
How to find the best Cliff Island package deals?
Use Expedia's filter tool to help you find some unbeatable Cliff Island package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Cliff Island package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
When to book a vacation package to Cliff Island?
If you have your Cliff Island vacation dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
