Chebeague Island Vacations from $475
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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.
The Latest Chebeague Island vacation packages
Price found within the past 48 hours. Click for updated prices.
The Wolfeboro Inn
Save 100% on your flight
Price was $912, price is now $576 per person
$576
per person
Aug 2 - Aug 5
found 6 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
8.2/10 Very Good! (588 reviews)
This Inn used to be so nice and well kept. It has seen better days. So much potential. Wish someone would come in and give it the makeover and facelift it desperately needs! Good bones, great location…needs attention!
Reviewed on Jul 2, 2026
Inn By The Sea
Save 100% on your flight
Price was $1,733, price is now $1,216 per person
$1,216
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.6/10 Exceptional! (322 reviews)
We just love it there. It is our happy place. Beautiful grounds, comfortable, friendly and downy to earth staff. Wonderful place!
Reviewed on Jun 26, 2026
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La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $165 total per night from Jul 5 to Jul 6
$165 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (2,181 reviews)
"Nothing special !"
Reviewed on Jul 2, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$304 nightly
The price is $336 total per night from Jul 5 to Jul 6
$336 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,777 reviews)
"Great room. Excellent location nice courtyard for food and drinks with firepit"
Reviewed on Jul 1, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
$256 nightly
The price is $283 total per night from Jul 5 to Jul 6
$283 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,256 reviews)
"We arrived to the hotel and were greeted by friendly staff. We opted out of the $40 valet parking and found free overnight parking on the street. The rooms were very clean, updated, and spacious. The bed was very comfortable. The location was perfect for getting around. I will definitely be ..."
Reviewed on Jul 2, 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.
Find the Best Chebeague Island Vacation Packages
Chebeague Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
Max Temp Winter | 30ºF |
Max Temp Summer | 70ºF |
Top Sights | State Theatre, East End Beach and Portland Museum of Art |
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- Eartha
- Visit Freeport
- Bailey Island Vacations
- Visit Bailey Island
- Peaks Island Vacations
- Portland Museum of Art
- East End Beach
- First Parish Church
- Bug Light
- Bailey Island Bridge
- Harrington House
- Bradbury Mountain State Park
- Bowdoin College
- Mackworth Island State Park
- Wilbur's of Maine Chocolate Confections
- Eastern Promenade
- Downtown Portland Vacations
- Little John Island Preserve
- Wolfe's Neck Woods State Park
- Two Lights State Park
- Paddleworks
- Victoria Mansion
- Casco Bay
- Clay Play
- Casco Bay Lines Ferry Terminal
- Spring Point Ledge Lighthouse
- Visit Old Port
- Visit Portland
- Land's End Gift Shop
- Ll Bean Flagship Store
- Portland Head Light
- Fort Williams Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.