Cliff Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Cliff Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Inn at St John Portland In-Town
Valley Street
CA $506
per person
Dec 10 - Dec 13
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Portland (PWM)
8.6/10 Excellent! (1,118 reviews)
Clean and friendly. Would not be a place for people who have trouble with stairs. The location seemed removed from waterfront activities but Portland is quite small and walkable. We would return.
Suggestion: With the shared bathroom, an exhaust fan and or air fresheners would go a long way.
Reviewed on Sep 22, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
CA $1,032
per person
Dec 10 - Dec 13
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Portland (PWM)
9.6/10 Exceptional! (61 reviews)
Best place ever!! We were so pleased we wanted to change up our trip to stay longer. If I could give 10 stars I would. Absolutely phenomenal!!
Reviewed on Sep 22, 2026
Portland Harbor Hotel
Downtown Portland
CA $718
per person
Dec 10 - Dec 13
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTZ) to Portland (PWM)
9.2/10 Wonderful! (1,823 reviews)
Cold water faucet not working properly. Laminate flooring had big gaps. Free coffee in the lobby, but walk 50 feet into the bistro and they charged me, what is with that? $45.00 per night to park your car is outrageous!
Reviewed on Sep 22, 2026
Ready to book your vacation to Cliff Island?
Cliff Island Hotel Deals
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundableReserve now, pay when you stay
CA $123
CA $135 total
Oct 18 - Oct 19
includes taxes & fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
CA $154
CA $168 total
Oct 18 - Oct 19
includes taxes & fees
8.4/10 Very good! (2,983 reviews)
"The place was spotless and the employees went above and beyond. I will definitely stay there again."
Reviewed on Sep 22, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
CA $151
CA $167 total
Oct 18 - Oct 19
includes taxes & 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.
Frequently asked questions
How much does a Cliff Island vacation package cost?
You can snap up a vacation package to this popular destination from CA $506 on Expedia. But how much your vacation to Cliff Island costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Cliff Island?
You're likely to find lower rates and better availability in January, February and March. Browse our cheap Cliff Island vacation packages and you could score some great off-season deals.
How many days is enough for Cliff Island?
The ideal duration of your Cliff Island vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to hit all the major sights and discover some hidden treasures along the way.
How to find the best Cliff Island package deals?
Use Expedia's filter tool to help you find some terrific Cliff Island package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Cliff Island package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Cliff Island vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Cliff Island trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cliff Island?
If you have your Cliff Island travel dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Cliff Island?
- Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to vacation in Cliff Island.
- Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Cliff Island.
- Decide your trip length: Think about how long you'd like to spend exploring Cliff Island. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Cliff Island vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
