Chebeague Island Vacations from $604
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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.
Evalina Hotel
Downtown Portland
$1,290
per person
Nov 12 - Nov 15
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Better than expected. This new property was in a great location. Easy to walk to restaurants and shopping. Comfortable bed, nice bathroom and a sitting area with sofa, chair and tv. I was a little concerned because we could hear music from a nearby bar, but everything stopped by 10 o’clock. Would return.
Reviewed on Sep 25, 2026
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Quality Inn & Suites South Portland
738 Main Street South Portland ME
Fully refundable
$69 nightly
$75 total
Nov 1 - Nov 2
Total with taxes and fees
6.4/10 (1,144 reviews)
"This is a very nice property and very clean. Staff were cordial. The hvac system worked well and wasn’t noisy. Room was clean. The room could have used a chair though. There was an office chair at the desk but the back wasn’t stable."
Reviewed on Sep 30, 2026
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$71 nightly
$78 total
Nov 1 - Nov 2
Total with taxes and fees
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
80 John Roberts Rd. South Portland ME
Fully refundable
$84 nightly
$92 total
Oct 25 - Oct 26
Total with taxes and fees
8.4/10 Very Good! (2,969 reviews)
"Great location. It had everything we needed."
Reviewed on Oct 1, 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 $604 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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- Flights from Columbus (CMH) to Portland (PWM)
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- Eartha
- Visit Freeport
- Bailey Island Vacations
- Visit Bailey Island
- Peaks Island Vacations
- 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.
