Chebeague Island Vacation Packages
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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.
Top Chebeague Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Saco Bay Hotel
Price was CA $1,113, price is now CA $895 per person
CA $895
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
7.6/10 Good! (1,051 reviews)
We just had a night stay there during a journey but it was comfortable and what we needed
Reviewed on May 7, 2026
Ogunquit River Inn & Suites
Price was CA $1,412, price is now CA $1,054 per person
CA $1,054
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The front desk was incredibly nice. They moved us closer to our family in another room without being asked. It was very appreciated, thank you.
Reviewed on May 3, 2026
Newagen Seaside Inn
Price was CA $1,278, price is now CA $1,045 per person
CA $1,045
per person
Jul 28 - Jul 30
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Portland (PWM)
9.4/10 Exceptional! (341 reviews)
IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back.
Reviewed on Oct 14, 2025
Portland Harbor Hotel
Downtown Portland
Price was CA $2,112, price is now CA $1,767 per person
CA $1,767
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Portland (PWM)
9.4/10 Exceptional! (1,753 reviews)
Really enjoyed our stay. Staff was great as well!
Reviewed on May 8, 2026
Chebeague Island Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from May 25 to May 26
CA $253
CA $333 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,757 reviews)
Really enjoyed our stay. Staff was great as well!
Reviewed on May 8, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from May 25 to May 26
CA $213
CA $235 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,642 reviews)
Very nice for pets!
Reviewed on May 7, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $227 per night from May 25 to May 26
CA $227
CA $289 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,209 reviews)
Great property. Always have a good stay. The rooms are clean and well laid out.
Reviewed on May 8, 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.
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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.
