Chebeague Island Vacations from $707
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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.
The Latest Chebeague Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street
Downtown Portland
$1,789
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (382 reviews)
This was me and my husband's first time to Maine and we brought our dog. We thought this place was Excellent in every way. It was in a great
location, walking distance to everything. Would definitely stay here again. Loved it!
Reviewed on Sep 9, 2026
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Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$92 nightly
$101 total
Sep 13 - Sep 14
Total with taxes and fees
6.4/10 (1,117 reviews)
"The property was very dirty, and there was too much noise at night. The room and the corridors smelled very bad. The receptionist at the front desk was also very rude. Overall, it was not a pleasant experience."
Reviewed on Sep 10, 2026
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
$123 nightly
$134 total
Sep 13 - Sep 14
Total with taxes and fees
8.4/10 Very Good! (3,002 reviews)
"This was a basic room, no frills. The smell of cleaning supplies was a little too much for me."
Reviewed on Sep 10, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$115 nightly
$127 total
Sep 20 - Sep 21
Total with taxes and fees
8.2/10 Very Good! (1,681 reviews)
"Our room was quite dated and in need of an upgrade. I did see a sign that renovations are planned, so hopefully this refers to the rooms. Otherwise everything was good."
Reviewed on Sep 10, 2026
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.
Find the Best Chebeague Island Vacation Packages
Chebeague Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | 30ºF |
Max Temp Summer | 70ºF |
Top Sights | State Theatre, East End Beach and Portland Museum of Art |
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Frequently asked questions
How much does a Chebeague Island vacation package cost?
You'll find cheap prices from $707 on Expedia for your Chebeague Island getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Chebeague Island costs.
What are the cheapest months to go to Chebeague Island?
If you'd like to book a cheap Chebeague Island vacation package, consider planning a trip in November, December and January. You'll typically find better prices on hotels and airfares during these months — perfect for budget-conscious travelers.
How many days is enough for Chebeague Island?
With a well-planned schedule, you can easily visit the top Chebeague Island attractions in a few days. But if you prefer to discover hidden spots or go on day trips, consider booking your Chebeague Island vacation for longer.
How to find the best Chebeague Island package deals?
Use Expedia's handy filters to help you find some tempting Chebeague Island package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Chebeague Island package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chebeague Island vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still get the freedom to create a customized Chebeague Island vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Chebeague Island?
If you have your Chebeague Island travel dates locked in, book as soon as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Chebeague Island vacation packages?
Jet off on your dream escape to Chebeague Island with our Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up bargains before they disappear.
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- Eartha
- Visit Freeport
- Bailey Island Vacations
- Visit Bailey Island
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- Portland Museum of Art
- East End Beach
- First Parish Church
- Bug Light
- Bailey Island Bridge
- Harrington House
- Bradbury Mountain State Park
- Bowdoin College
- Mackworth Island State Park
- Wilbur's of Maine Chocolate Confections
- Eastern Promenade
- Downtown Portland Vacations
- Little John Island Preserve
- Wolfe's Neck Woods State Park
- Two Lights State Park
- Paddleworks
- Victoria Mansion
- Casco Bay
- Clay Play
- Casco Bay Lines Ferry Terminal
- Spring Point Ledge Lighthouse
- Visit Old Port
- Visit Portland
- Land's End Gift Shop
- Ll Bean Flagship Store
- Portland Head Light
- Fort Williams Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
