Chebeague Island Vacations from $571

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Price was $682, price is now $571 per person
$571
per person
Nov 15 - Nov 19
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (347 reviews)
Nice and convenient

Reviewed on Oct 3, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,096 per person
$1,096
per person
Nov 15 - Nov 19
found 13 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (1,007 reviews)
Beautiful clean room with the most amazing views! Staff is very friendly and shoutout to Mark and Mariam for welcoming my kids with some fun snacks after our long trip to get here! Words can’t describe our experience at the Cliff House.. just WOW!

Reviewed on Oct 4, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,106, price is now $903 per person
$903
per person
Nov 15 - Nov 19
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (281 reviews)
Absolutely 5 star. Best bed I’ve slept in at a hotel bar none.

Reviewed on Sep 10, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Price was $1,075, price is now $885 per person
$885
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.4/10 Exceptional! (622 reviews)
I honestly felt overwhelmed after checking in. That would be my only "complaint". Fantastic property but I feel there is probably more to it that I'm not even taking advantage of.

Reviewed on Oct 3, 2025

Don't see what you're looking for?
See all available trips from Columbus to Chebeague Island
View all trips

Chebeague Island Hotel Deals

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Nov 2 to Nov 3
$103 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,103 reviews)
Pleasant Stay Despite Looks
"Front desk guest service was friendly, easy, and reliable. The room was more spacious than I anticipated, although the bathroom was as small as you’d expect. They only have bars of soap for the bathroom. I did a quick trip so I thought it was better than expected. There are noticeable areas that ..."

Reviewed on Sep 30, 2025

Clarion Hotel Portland
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
$85 nightly
The price is $93 total per night from Nov 6 to Nov 7
$93 total
Nov 6 - Nov 7
Total with taxes and fees
7.4/10 Good! (288 reviews)
"It was convenient right off the highway. The room was clean and comfortable and the staff was friendly"

Reviewed on Oct 2, 2025

Germaine Inn South Portland
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $122 total per night from Nov 2 to Nov 3
$122 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,047 reviews)
"Rooms are comfortable and it is very quiet here"

Reviewed on Sep 30, 2025

Fireside Inn & Suites Portland
See all 2,218 properties in Chebeague Island
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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chebeague Island vacation package cost?
You'll find cheap prices from $571 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.