
Chebeague Island Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 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
Your Chebeague Island Holiday
An easy way to experience this exciting city is with a custom-made Chebeague Island holiday package. Stay in the neighbourhood of Parkside, which is good for festivals, markets and walking or go someplace else — our packages are all about you. Make your trip to Chebeague Island even more fun by going sightseeing. Wolfes Neck Woods State Park, Bailey Island Bridge and Little John Island Preserve are among the major attractions you'll want to explore. No matter your travel plans or the size of your budget, organising a tailored Chebeague Island holiday is a piece of cake with Expedia.
Chebeague Island Holiday
Chebeague Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 21ºC |
Top Sights | State Theatre, Portland Museum of Art and East End Beach |
Our pick of the best Chebeague Island Hotel Deals

Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$322 per night from 10 May to 11 May
AU$322
10 May - 11 May
includes taxes & fees
9.4/10 Exceptional! (1,748 reviews)
We (and our kids!) loved the “pantry” on each floor — fruit, snacks, cookies, tea, coffee. It was a much-appreciated surprise. Room was clean and quiet, and all staff were friendly and helpful.
Reviewed on 29 Apr 2026

HomeAwhile
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is AU$195 per night from 3 May to 4 May
AU$195
3 May - 4 May
includes taxes & fees
9.2/10 Wonderful! (30 reviews)
Check in was a nightmare. Key machine did not work and it took over an hour to get in to a room where the key only worked once. After finally getting in I was assigned a different room as we couldn ’t get the key to work.
Reviewed on 30 Apr 2026

Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is AU$267 per night from 3 May to 4 May
AU$267
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (1,200 reviews)
First day my room wasn't cleaned ! Thought I'd get some complimentary water , but only had for first night !
Reviewed on 1 May 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.
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.











