Chebeague Island Vacation Packages
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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.
Kennebunkport Captains Collection
CA $1,920
per person
Sep 21 - Sep 25
found 2 hours ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
9.4/10 Exceptional! (728 reviews)
Gorgeous and extremely safe and peaceful town. This property is awesome. We bought wine and cheese from Maine &Vine and enjoyed them on the lush lawn under the trees. They have beach chairs and bikes, too. Breakfast is included and wonderful. Then there is the chocolate chip cookies with sea salt. Oh my!!
Reviewed on Aug 9, 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 8 - Sep 9
includes taxes & fees
7.4/10 Good! (655 reviews)
"Reserved a room with 2 beds. Got to room had 1 bed. Went to front desk. They said no rooms with 2 beds available. I asked for a cot or something like that. They said they had none available. I asked for linens. They said none available. Instead of 4 people in 2 beds, we put 3 people in 1 bed and ..."
Reviewed on Aug 9, 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
8/10 Very good! (1,620 reviews)
"My daughter and I did a daddy/daughter vacation and chose this hotel as part of package deal which was not a good deal in any way. This hotel one of the few with a hot tub. We could not reserve 2 beds but on arrival the front desk staff was great and gave us 2 rooms. It's important to recognize that ..."
Reviewed on Aug 10, 2026
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 $944 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.
