Chebeague Island Vacations from $728

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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.
River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (291 reviews)
It was a basic suite-like motel. Could use an upgrade. Very 70s

Reviewed on Mar 30, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
The Cliff House is a one of a kind! Always a fantastic visit!

Reviewed on Aug 1, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (31 reviews)
Away from the busy areas but not far ton

Reviewed on Jul 29, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (64 reviews)
We had a great stay in the 2 bedroom unit. great set up and was super clean. Loved the proximity to the shopping area and restaurants. Only issue was the front door lock, noticed a lot of the other people were leaving the lock open. Would stay here again

Reviewed on Jul 24, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (218 reviews)
Fantastic place to stay when visiting Portland. The location can't be beat -- within a couple of blocks to the ferry terminal and Old Town shops and restaurants. The building is next to a police station and my family and I felt very safe. The unit was immaculate, modern, and fully equipped. Onsite parking was a huge bonus, as was the friendly and helpful staff. I would, without hesitation, stay at The Docent's Collection again.

Reviewed on Jul 31, 2025

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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
$152 nightly
The price is $168 total per night from Aug 11 to Aug 12
$168 total
Aug 11 - Aug 12
Total includes taxes and fees
7.8/10 Good! (1,001 reviews)
"Breakfast food served out of a closet was a little odd, but it did taste good."

Reviewed on Aug 1, 2025

Clarion Hotel Portland
Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $120 total per night from Aug 24 to Aug 25
$120 total
Aug 24 - Aug 25
Total includes taxes and fees
7.8/10 Good! (1,095 reviews)
"Good"

Reviewed on Jul 30, 2025

Days Inn by Wyndham Airport/Maine Mall
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $146 total per night from Aug 5 to Aug 6
$146 total
Aug 5 - Aug 6
Total includes taxes and fees
8.4/10 Very Good! (1,444 reviews)
"Very friend staff"

Reviewed on Aug 1, 2025

Comfort Inn Airport
See all 2,341 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.

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Frequently asked questions

How much does a Chebeague Island vacation package cost?
You'll find cheap prices from $728 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.