Chebeague Island Vacations from $670
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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 $1,151, price is now $670 per person
$670
per person
Sep 4 - Sep 7
found 23 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
We were greeted with friendliness and appreciation and a complimentary beverage and it felt like they were trying the whole time to do a good job. What else can you ask for?
Reviewed on Jul 2, 2026
The Weldon Hotel
Downtown Portland
Save 100% on your flight
Price was $1,893, price is now $1,232 per person
$1,232
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless,
Great location. Would stay here again
Reviewed on Apr 23, 2026
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $2,395, price is now $1,566 per person
$1,566
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (185 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
Evalina Hotel
Downtown Portland
Save 100% on your flight
Price was $1,817, price is now $1,218 per person
$1,218
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop 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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La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $162 total per night from Jul 7 to Jul 8
$162 total
Jul 7 - Jul 8
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
$331 nightly
The price is $366 total per night from Jul 5 to Jul 6
$366 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,776 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! (1,255 reviews)
"Front desk and the other staff we encountered were friendly, thoughtful, and accommodating. Lovely experience for out-of-state visitors looking to explore the adventures of the Portland culinary landscape."
Reviewed on Jul 1, 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.
