Chebeague Island Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Chebeague Island Holiday
Our pick of the best Chebeague Island Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$162 per night from 24 Dec to 25 Dec
NZ$162
24 Dec - 25 Dec
includes taxes & fees
7.8/10 Good! (1,292 reviews)
Great room. Courteous staff.
Reviewed on 21 Dec 2025
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$171 per night from 5 Jan to 6 Jan
NZ$171
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Helpful staff
Reviewed on 17 Dec 2025
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,547 reviews)
The location was perfect. It was very close to shopping, restaurants and the waterfront. The room was nice and clean. The hot tub was closed for several days for cleaning so we could not use which was a major bummer as we really really wanted to use it. Staff super friendly. Valet parking for $35 ...
Reviewed on 17 Dec 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.
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.
