Casco Bay Islands Vacations from $830
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The Latest Casco Bay Islands 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 $1,241, price is now $830 per person
$830
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Room was very comfortable. A/C worked too well! Easy check in. Would stay here again definitely. Worth the extra cost for balcony room.
Reviewed on Jul 16, 2026
Blind Tiger Portland – Carleton Street
West End
Save 100% on your flight
Price was $1,601, price is now $1,030 per person
$1,030
per person
Sep 6 - Sep 9
just found
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (124 reviews)
Excellent private boutique home, converted to hotel. No person greets you and there is no welcome desk. You put in a code on the door to enter and instructions are given via text. No elevator and 3 stories, so keep that in mind. Would HIGHLY recommend.
Reviewed on Jul 16, 2026
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $1,301, price is now $843 per person
$843
per person
Sep 6 - Sep 9
just found
Roundtrip non-stop flight included
Chicago (CHI) 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
Evalina Hotel
Downtown Portland
Save 100% on your flight
Price was $1,679, price is now $1,173 per person
$1,173
per person
Sep 25 - Sep 28
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
The Meadowmere Resort
Save 100% on your flight
Price was $1,484, price is now $1,051 per person
$1,051
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Staff was very helpful, room was clean, and great location! Would definitely stay there again
Reviewed on Jul 14, 2026
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Casco Bay Islands Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
$144 nightly
The price is $159 total per night from Jul 27 to Jul 28
$159 total
Jul 27 - Jul 28
Total with taxes and fees
8.2/10 Very Good! (1,557 reviews)
"Free parking. Good staff. Great location. Good value."
Reviewed on Jul 17, 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $167 total per night from Jul 19 to Jul 20
$167 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (1,035 reviews)
"The Inn was clean and comfortable"
Reviewed on Jul 17, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
$279 nightly
The price is $309 total per night from Jul 26 to Jul 27
$309 total
Jul 26 - Jul 27
Total with taxes and fees
9.4/10 Exceptional! (1,246 reviews)
"Excellent space, great location, very comfortable room and hotel."
Reviewed on Jul 16, 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 Casco Bay Islands Vacation Packages
Casco Bay Islands Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Portland Intl. Jetport Airport (PWM) |
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- Umbrella Cover Museum
- Bailey Island Vacations
- Spring Point Ledge Lighthouse
- Victoria Mansion
- Eastern Promenade
- Little John Island Preserve
- Land's End Gift Shop
- Portland Head Light
- Bug Light
- Eartha
- Portland Museum of Art
- Bailey Island Bridge
- Visit Bailey Island
- Higgins Beach
- Ll Bean Flagship Store
- International Cryptozoology Museum
- Fort Williams Park
- Mackworth Island State Park
- Two Lights State Park
- Goddard Mansion
- Casco Bay Lines Ferry Terminal
- Clay Play
- Peaks Island Vacations
- Casco Bay
- Chebeague Island Vacations
- Visit Freeport
- Bowdoin College
- Fort Preble
- Visit Portland
- Downtown Portland Vacations
- East End Beach
- Bradbury Mountain State Park
- Visit Old Port
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.