Cliff Island Vacations from $428

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Cliff Island vacation packages

Price found within the past 48 hours. Click for updated prices.
84 Main
Cliff House Maine
Portland Harbor Hotel
Blind Tiger Portland - Danforth Street.
The Kennebunk Inn
Don't see what you're looking for?
See all available trips from Columbus to Cliff Island
View all trips

Cliff Island Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $183 total per night from Nov 16 to Nov 17
$183 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (1,666 reviews)
Great rooms, walk-able to everything, super clean, great staff, the restaurant is delicious and the bar has good drinks, very accommodating and lots of extras! The 4 stars are for parking... we would like to keep our car inside the garage, to do so it must be valet, that is not an option for some ...

Reviewed on Nov 12, 2025

Portland Harbor Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 20 to Nov 21
$92 total
Nov 20 - Nov 21
Total with taxes and fees
7.8/10 Good! (1,222 reviews)
I've stayed here a few times and have always had a good experience. Staff is always welcoming and the rooms are

Reviewed on Nov 9, 2025

Clarion Hotel Portland
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road, South Portland, ME
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Nov 20 to Nov 21
$86 total
Nov 20 - Nov 21
Total with taxes and fees
8.8/10 Excellent! (1,609 reviews)
Absolutely

Reviewed on Nov 12, 2025

Tru by Hilton Portland Airport Area
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.

Find the Best Cliff Island Vacation Packages

More vacations you might like

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.