
Chebeague Island Vacations from $328
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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.

Ramada Plaza by Wyndham Portland
Nasons Corner
Price was $410, price is now $328 per person
$328
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
7.8/10 Good! (1,052 reviews)
Property is good . Nice area and convenient
Reviewed on Aug 22, 2025

Cliff House Maine
Save 100% on your flight
Price was $1,741, price is now $1,147 per person
$1,147
per person
Oct 3 - Oct 6
found 3 hours ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
We had an amazing stay at Cliffhouse and were pleasantly surprised by how beautiful it is. The only minor issues we encountered were that the pullout couch was quite uncomfortable for our kids, and it was frustrating that children aren’t allowed in the main pool—everyone with kids ends up crowded around a small pool off to the side. Aside from that, everything else was fantastic!
Reviewed on Aug 9, 2025

The McKernan Inn
Price was $706, price is now $537 per person
$537
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9/10 Wonderful! (47 reviews)
Quiet and peaceful with views of the Bay. Easy to access and close to downtown Portland
Reviewed on Aug 18, 2025

The Docent's Collection
Downtown Portland
Price was $1,569, price is now $1,274 per person
$1,274
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
9.6/10 Exceptional! (226 reviews)
I had a wonderful stay! The place was clean, cozy, and exactly as described. The location was perfect, which made everything smooth and easy. I’d happily stay here again and recommend it to anyone visiting Portland.
Reviewed on Aug 22, 2025

Microtel Inn & Suites by Wyndham York
Price was $848, price is now $699 per person
$699
per person
Sep 26 - Oct 3
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
8/10 Very Good! (1,000 reviews)
Staff were very attentive. Breakfast was well done. Pool was great. Location was excellent.
Reviewed on Aug 14, 2025
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Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $127 total per night from Aug 24 to Aug 25
$127 total
Aug 24 - Aug 25
Total with taxes and fees
7.8/10 Good! (1,223 reviews)
Excellent choice for single night stay
"Very convenient hotel for those flying into PWM. Quick stop on the way to Rockland. Front desk was pleasant. Got me toothpaste I forgot. Told them about stopped up sink and they noted it. (It wasn't an issue for me as I simply removed the stopper and left it on the counter to be cleaned.) Breakfast ..."
Reviewed on Aug 22, 2025

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 26 to Aug 27
$168 total
Aug 26 - Aug 27
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
"I like the room and accommodations. The front desk person was a bit brief with me though."
Reviewed on Aug 22, 2025

Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $141 total per night from Sep 2 to Sep 3
$141 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,043 reviews)
"The hotel was good enough for the time being (felt safe, clean, etc) but was overall just an okay property."
Reviewed on Aug 20, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.