A wooden pier leading to a marina with boats docked.

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.

    Chebeague Island Hotel Deals

    Spark by Hilton Freeport

    A room with a green carpet, two rocking chairs, a small table with a potted plant, a window with a view of greenery, and a coffee station with dispensers.
    • Address: 107 US Route 1, Freeport, ME, 04032, US
    • Location: 8.9 km from Chebeague Island
    • Star rating: 2/5
    • Guest rating: 8.8/10 (Excellent, 44 reviews)
    • Price: CA $116, CA $126 total, includes taxes & fees, Nov 30 - Dec 1

    Holiday Inn Express Hotel & Suites Freeport by IHG

    A Holiday Inn Express building with a covered entrance and a clear sky.
    • Address: 450 U.S. Route 1, Freeport, ME, 04032, US
    • Location: 10.6 km from Chebeague Island
    • Star rating: 2.5/5
    • Guest rating: 8.8/10 (Excellent, 1002 reviews)
    • Price: CA $133, CA $144 total, includes taxes & fees, Nov 16 - Nov 17

    Hampton Inn Freeport/Brunswick

    A hotel lobby with a seating area, a snack bar, and a refrigerator.
    • Address: 194 Lower Main St, Freeport, ME, 04032, US
    • Location: 11.6 km from Chebeague Island
    • Star rating: 2.5/5
    • Guest rating: 9/10 (Wonderful, 1002 reviews)
    • Price: CA $139, CA $152 total, includes taxes & fees, Nov 22 - Nov 23

    SpringHill Suites by Marriott Freeport Brunswick

    An outdoor patio with a fire pit, seating area, and chairs.
    • Address: 500 US-1, Freeport, ME, 04032, US
    • Location: 10.8 km from Chebeague Island
    • Star rating: 2/5
    • Guest rating: 8.8/10 (Excellent, 333 reviews)
    • Price: CA $132, CA $144 total, includes taxes & fees, Nov 15 - Nov 16

    The Freeport Hotel, an Ascend Collection Hotel

    A modern living room with a sofa, ottoman, and chairs, a kitchen area with a counter and pendant lights, and a large window with curtains.
    • Address: 506 Us Route 1, Freeport, ME, 04032, US
    • Location: 10.9 km from Chebeague Island
    • Star rating: 2/5
    • Guest rating: 7.6/10 (Good, 1001 reviews)
    • Price: CA $118, CA $129 total, includes taxes & fees, Nov 15 - Nov 16

    Best Western Freeport Inn

    A hotel room with a bed, a nightstand, a lamp, a view of a forest through a sliding door, and a balcony with curtains.
    • Address: 31 US Route 1, Freeport, ME, 04032, US
    • Location: 8.7 km from Chebeague Island
    • Star rating: 3/5
    • Guest rating: 7.6/10 (Good, 1000 reviews)
    • Price: CA $126, CA $137 total, includes taxes & fees, Nov 17 - Nov 18

    Inn On Peaks Island

    A two-story building with a balcony and a sign reading "The Inn on Peaks Island".
    • Address: 33 Island Avenue, Peaks Island, ME, 04108, US
    • Location: 12 km from Chebeague Island
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 122 reviews)
    • Price: CA $191, CA $208 total, includes taxes & fees, Nov 15 - Nov 16
    • Review: Amazing view! Quiet, quaint and perfect

    Econo Lodge Freeport - Brunswick Area

    A breakfast buffet with pastries, coffee, and condiments.
    • Address: 537 Route 1 South, Freeport, ME, 04032, US
    • Location: 11 km from Chebeague Island
    • Star rating: 2/5
    • Guest rating: 7.4/10 (Good, 1001 reviews)
    • Price: CA $113, CA $123 total, includes taxes & fees, Dec 14 - Dec 15
    • Review: Heat was not working in our first room. They moved us to another room, where the microwave was not working. The heat worked, but we were told that the microwave in the room did not work. The room as FILTHY.

    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 Chebeague Island

    Frequently Asked Questions

    How much does a Chebeague Island vacation package cost?

    You can grab a vacation package to this popular destination 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?

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