Cliff Island Vacations from $587
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The Latest Cliff Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort
$1,060
per person
Dec 7 - Dec 13
found 11 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
8.6/10 Excellent! (1,008 reviews)
Check in was a nightmare, the room I paid for in full before the stay was not available (over booked) downgraded to a queen room, young man at check in was rides fold me it was my fault bc used Expedia. Finally got a room key after that din exchange and walked into a lady in bed! So apparently all the rooms were ‘double booked’ the manager did come talk to us, he was very nice, he got us into the queen room and told us he’d comp a return night (hasn’t happened yet).
The resort is lovely, clean and spa area is great. Walkable to in town restaurants.
Beds are comfortable and rooms are clean and updated.
If not for the horrible check in and attitude I’d give this stay 5 stars, but tough to do when you paid for something you didn’t get. Expedia declined to refund any of what we paid, they said the resort had to and the resort said they had to …
Reviewed on Oct 17, 2026
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View all tripsCliff Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$83 nightly
$92 total
Oct 25 - Oct 26
Total with taxes and fees
8.2/10 Very Good! (1,788 reviews)
"Suitable for overnight stay. Outdated rooms, but clean & bed was comfortable enough. A bit overpriced for the quality, but free parking."
Reviewed on Oct 19, 2026
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$108 nightly
$119 total
Nov 18 - Nov 19
Total with taxes and fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$87 nightly
$96 total
Nov 4 - Nov 5
Total with taxes and fees
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.
