Chebeague Island Vacation Packages
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- 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
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Your Chebeague Island Vacation
Book a Chebeague Island vacation package that has only the things you need and nothing you don't. Good for festivals, markets and walking, consider staying in the neighborhood of Parkside. If a sightseeing tour is part of the program during your trip to Chebeague Island, check out major attractions like Eagle Island, Little John Island Preserve and Sturdivant Island. That dream Chebeague Island vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.
Top Chebeague Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
Moody
CA $849
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
We LOVED this property. The staff was BEYOND helpful and amazing. The rooms were clean. The beds were comfortable. The pool was perfect!
The property is BEAUTIFUL
Reviewed on Aug 10, 2026
Admiral Peary Inn
CA $908
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
8.8/10 Excellent! (55 reviews)
Had a wonderful one night stay at this property. Everything was spotless and top notch. Even walked into the common kitchen area to find fresh baked cookies for the guests.
Reviewed on Aug 7, 2026
Inn By The Sea
CA $1,426
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (327 reviews)
(+)
Location
Dog Friendly
Food
Parking
Everything you would expect from a luxury hotel - it is pricy.
Nothing negative.
Reviewed on Aug 2, 2026
AWOL Kennebunkport
CA $1,155
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (250 reviews)
Wonderful historic property updated with in-house suites & cabin-style lodgings. Adequate parking. Room was comfortable, new bathrooms & nice breakfast area. The breakfast itself was TDF!! The neighborhood is authentic. Walkable to downtown. Highly recommend.
Reviewed on Jul 20, 2026
Ready to book your vacation to Chebeague Island?
Chebeague Island Hotel Deals
Clarion Pointe South Portland
675 Main Street I-95 South Portland ME
Fully refundable
CA $129
CA $141 total
Sep 9 - Sep 10
includes taxes & fees
7.2/10 Good! (662 reviews)
"Clean room, not far from Old Port to where people hang out. Simple breakfast, gym and pool and a good place to stay"
Reviewed on Aug 10, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $182
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
CA $134
CA $146 total
Aug 30 - Aug 31
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 Chebeague Island vacation package cost?
You can grab a vacation package to this popular destination from CA $849 on Expedia. However, how much your vacation to Chebeague Island costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Chebeague Island?
To score cheap Chebeague Island vacation packages, organize your trip outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Chebeague Island?
With around 2 days, you'll have enough time to visit popular neighbourhoods like Cousins Island and Town Landing during your Chebeague Island vacation. Be sure to also add Eagle Island and Winslow Memorial Park to your must-see list. In the mood for more adventures? Consider exploring outside of Chebeague Island on tours and day trips.
How to find the best Chebeague Island package deals?
Start your search for a Chebeague Island package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Chebeague Island package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chebeague Island getaway off to a flying start.
Is it cheaper to book a Chebeague Island vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can customize your Chebeague Island trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Chebeague Island?
If you have your Chebeague Island travel dates confirmed, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Chebeague Island?
- Pick your travel dates: The things you want to do in Chebeague Island and your favourite season will help you decide when to get away.
- Set a budget: Factor in expenses such as flights, transportation and food when working out how much to save for your trip to Chebeague Island. Then, pick a property that matches your budget, whether that's an economical stay or a high-end retreat.
- Determine how many days away: Start by listing all the activities and sights you'd like to get to in Chebeague Island. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Chebeague Island vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
