
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.




The Weldon Hotel
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
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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Clarion Hotel Portland
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

Days Inn by Wyndham Airport/Maine Mall
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

Comfort Inn Airport
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
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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