
Chebeague Island Holidays
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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

The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 28 Apr to 29 Apr
AU$189
28 Apr - 29 Apr
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
The rooms are always great. We stay here every time we go to Portland. THE MOST COMFORTABLE BEDS AND PILLOWS I EVER HAD IN A HOTEL! Great experience, as always!
Reviewed on 23 Apr 2026

Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 28 Apr to 29 Apr
AU$265
28 Apr - 29 Apr
includes taxes & fees
9.2/10 Wonderful! (1,746 reviews)
Portland Harbor Hotel was in a great location to explore the downtown and harbor area. It’s very close to lots of shops and restaurants.
Reviewed on 23 Apr 2026

HomeAwhile
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 21 May to 22 May
AU$177
21 May - 22 May
includes taxes & fees
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.











