A rocky shoreline with a lighthouse and a calm sea under a colorful sky.

Peaks Island Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Peaks Island Vacation

With plenty of highlights as well as some hidden gems, this city is best experienced with a Peaks Island vacation package. Check out places to stay in Parkside, which is great for festivals, markets and walking. If taking in sights is on the agenda during your trip to Peaks Island, look around major attractions like Sand Beach, Fifth Maine Museum and Little Diamond Island. Check out Expedia's wide range of travel options and book your ideal vacation to Peaks Island today.

The Latest Peaks Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 24 - Dec 29

    Portland Harbor Hotel + Flight

    Downtown Portland
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,863 reviews)
    "Great location and spacious rooms. We brought our dog too! Loved grabbing a pre dinner drink and sitting by the cozy fireplace."
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $1,382
    CA $1,155
    per traveller
    found 1 day ago
    Portland Harbor Hotel
  • Dec 24 - Dec 29

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    5 nights
    3.5 star property
    9.6/10 - Exceptional (427 reviews)
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $2,112
    CA $1,579
    per traveller
    found 1 day ago
    The Docent's Collection at 121 Middle Street
  • Dec 24 - Dec 29

    Inn By The Sea + Flight

    Cape Elizabeth
    5 nights
    4.0 star property
    9.6/10 - Exceptional (345 reviews)
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $1,762
    CA $1,476
    per traveller
    found 1 day ago
    Inn By The Sea
  • Dec 24 - Dec 29

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    5 nights
    3.5 star property
    9.6/10 - Exceptional (204 reviews)
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $2,208
    CA $1,934
    per traveller
    found 1 day ago
    Blind Tiger Portland - Danforth Street.
  • Dec 24 - Dec 29

    Portland Regency Hotel & Spa + Flight

    Downtown Portland
    5 nights
    3.5 star property
    9.4/10 - Exceptional (1,807 reviews)
    "Staff at the reception was not very warm and friendly at both check in and check out. However the valet staff and lounge staff were very kind and hospitable."
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Portland (PWM)
    YYZ - PWM • 1 stop PWM - YYZ • 1 stop
    CA $1,354
    CA $1,189
    per traveller
    found 1 day ago
    Portland Regency Hotel & Spa

Discover the most popular places to visit in Peaks Island

What to do in Peaks Island

Peaks Island Hotel Deals

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 Peaks Island vacation package cost?

You'll find cheap prices from CA $1,155 on Expedia for your Peaks Island break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Peaks Island costs.

What are the cheapest months to go to Peaks Island?

November, December and January are the best times to search for cheap Peaks Island vacation packages. Choosing to travel in less busy months means you can typically find lower prices on accommodations and flights.

How many days is enough for Peaks Island?

Peaks Island vacations come in many shapes and sizes, but to really get a feel for this destination, we'd suggest 2 days is a good ballpark. With this timeframe, you can fit in top sights like Portland Museum of Art and East End Beach along with lesser-known spots. Don't miss out on cool neighbourhoods such as Downtown Portland and Old Port either. If you're clever with your time, you can even allow for a day trip outside of Peaks Island too.

Is it worth booking a vacation package to Peaks Island?

Popular for its watersports, views and cycling, a Peaks Island vacation is a hit with all kinds of travellers. Be sure to check out top sights like Fifth Maine Museum and Richard Boyd Art Gallery, and consider renting a car for day trips to experience even more.

How to find the best Peaks Island package deals?

Landing a cheap Peaks Island package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Peaks Island package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.

Is it cheaper to book a Peaks Island vacation as a package?

You can enjoy significant savings on your Peaks Island break by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Peaks Island?

If you have your Peaks Island travel dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for jetting off on a whim.

How to plan a trip to Peaks Island?

  1. Choose when to get away: Check your diary and get packing. Your favourite season and the type of activities on offer will also help you decide when to visit Peaks Island.
  2. Budget wisely: Besides the cost of your hotel, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Peaks Island.
  3. Decide your trip length: Consider how long you want to spend exploring Peaks Island. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Peaks 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.