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Cliff Island Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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The Latest Cliff Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Oct 2 - Oct 5

    Dormir + Flight

    Windham
    3 nights
    3.0 star property
    9.0/10 - Wonderful (1,002 reviews)
    "Great location if you're looking to experience the lake. Staff was very helpful."
    Reviewed August 6, 2026
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - BOS • Nonstop BOS - YYZ • Nonstop
    CA $1,111
    CA $797
    per traveller
    found 1 day ago
    Dormir
  • Front of property
    Oct 18 - Oct 24

    Evalina Hotel + Flight

    Downtown Portland
    6 nights
    2.5 star property
    10/10 - Exceptional (8 reviews)
    "Evalina was more than we expected. Super clean and has every convenience item imaginable. The beds were super comfortable. The communication was spectacular which made everything from check in to checkout s smooth. We will definitely be back and hopefully for a longer stay next time."
    Reviewed August 4, 2026
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $3,949
    CA $2,854
    per traveller
    found 1 day ago
    Evalina Hotel
  • Baxter
    Oct 18 - Oct 22

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    4 nights
    3.5 star property
    9.6/10 - Exceptional (189 reviews)
    "This hotel is amazing. The rooms, beds, and all the details are so incredible. I wish I could have stayed longer. Check in was a breeze as well. You can tell they take a lot of care and thought into the property. I will definitely be back"
    Reviewed July 25, 2026
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $3,374
    CA $2,607
    per traveller
    found 1 day ago
    Blind Tiger Portland - Danforth Street.
  • Exterior
    Oct 18 - Oct 24

    Portland Regency Hotel & Spa + Flight

    Downtown Portland
    6 nights
    3.5 star property
    9.4/10 - Exceptional (1,717 reviews)
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $2,610
    CA $2,024
    per traveller
    found 1 day ago
    Portland Regency Hotel & Spa
  • Indoor pool, sun loungers
    Sept 6 - Sept 12

    River View Resort + Flight

    Bethel
    6 nights
    2.5 star property
    9.0/10 - Wonderful (332 reviews)
    "The room was clean (but a bit dated), and comfortable. Staff was welcoming and very friendly. It was perfect to stay w/ my mother and teen-aged son. It was nice to have a full kitchen, and conveniently supplied with the essentials. We would stay there again!"
    Reviewed August 4, 2026
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YTZ - BOS • Nonstop BOS - YTZ • Nonstop
    CA $1,707
    CA $1,334
    per traveller
    found 2 hours ago
    River View Resort

Cliff Island Hotel Deals

Exterior

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine
3.5 star property
17.1 km from Cliff Island
9.4 out of 10, Exceptional, (1,170 reviews)
"This is a nice family friendly hotel. It is ny the airport about 15 minutes from the Downtown area. The good: very friendly staff and a great breakfast. The bad: the design of the hotel is different than other Embassy Suites. Also note that they charge $13 for parking."
The price is CA $321
CA $355 total
includes taxes & fees
Sep 1 - Sep 2
Embassy Suites by Hilton Portland Maine
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.
See all properties in Cliff Island

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 $797 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.