Chebeague Island Holidays
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Your Chebeague Island Holiday
Book a Chebeague Island holiday package that has only the things you need and nothing you don't. Good for festivals, markets and walking, consider staying in the neighbourhood of Parkside. If a sightseeing tour is part of the programme during your trip to Chebeague Island, check out major attractions like Eagle Island, Little John Island Preserve and Sturdivant Island. That dream Chebeague Island holiday is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your style.
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, East End Beach and Portland Museum of Art |
Top hotels in Chebeague Island
Portland Harbor Hotel
468 Fore Street Portland ME
The price is £165 per night from 10 May to 11 May
£165
10 May - 11 May
includes taxes & fees
9.4/10 Exceptional! (1,754 reviews)
Hotel was within walking distance to everything we wanted! Friendly, helpful staff, bartender was great! Extremely clean hotel, would absoulty stay again!
Reviewed on 4 May 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is £129 per night from 26 May to 27 May
£129
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (1,641 reviews)
Excellent location & great service throughout.
Reviewed on 6 May 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
The price is £148 per night from 10 May to 11 May
£148
10 May - 11 May
includes taxes & fees
9.4/10 Exceptional! (1,205 reviews)
This was a very relaxing stay with a helpful
Reviewed on 5 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.
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- Portland Head Light
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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. Flight-inclusive packages are ATOL protected.
