Chebeague Island Vacations from $521
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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.
Ogunquit River Inn & Suites
Moody
Save 100% on your flight
Price was $836, price is now $521 per person
$521
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Clean room , great and friendly staff , great location
Reviewed on Jul 13, 2026
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $2,223, price is now $1,395 per person
$1,395
per person
Oct 3 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.6/10 Exceptional! (188 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.
Reviewed on Jun 26, 2026
The Meadowmere Resort
Save 100% on your flight
Price was $1,520, price is now $1,038 per person
$1,038
per person
Sep 4 - Sep 7
found 13 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Everyone who worked there was helpful and very friendly.
Reviewed on Jul 13, 2026
Evalina Hotel
Downtown Portland
Save 100% on your flight
Price was $1,788, price is now $1,252 per person
$1,252
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.
Reviewed on Jun 28, 2026
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Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$144 nightly
The price is $159 total per night from Jul 26 to Jul 27
$159 total
Jul 26 - Jul 27
Total with taxes and fees
8.2/10 Very Good! (1,556 reviews)
"Love the hot tub although it obviously was not cleaned after closing between 10p-6a There were no towels available at 6:30 am The floor surface of the pool area needs attention. The pebble surface is loose and pulling up in some ares and pebbles are getting tracked int to pool. We enjoyed using the ..."
Reviewed on Jul 13, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
$323 nightly
The price is $357 total per night from Jul 26 to Jul 27
$357 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (1,268 reviews)
"Clean rooms,welcoming stagf"
Reviewed on Jul 13, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
$423 nightly
The price is $468 total per night from Jul 26 to Jul 27
$468 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (1,784 reviews)
"Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!"
Reviewed on Jul 12, 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.
