Search Deals onCasco Bay Islands Vacation Packages
Casco Bay Islands Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview
Price was $562, price is now $424 per person
$424
per person
Mar 18 - Mar 22
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Portland Stage are located nearby.
The Docent’s Collection – Thompson Block
Save 100% on your flight
Price was $795, price is now $563 per person
$563
per person
Mar 18 - Mar 22
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
Portland Harbor Hotel
Price was $621, price is now $463 per person
$463
per person
Mar 18 - Mar 22
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.
Portland Regency Hotel & Spa
Price was $643, price is now $482 per person
$482
per person
Mar 18 - Mar 22
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Inn By The Sea
Price was $903, price is now $694 per person
$694
per person
Mar 18 - Mar 22
found 18 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Blind Tiger Portland - Danforth Street.
Price was $836, price is now $650 per person
$650
per person
Mar 18 - Mar 22
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Kennebunkport Captains Collection
Price was $860, price is now $688 per person
$688
per person
Mar 18 - Mar 22
found 18 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.
Embassy Suites by Hilton Portland Maine
Price was $579, price is now $467 per person
$467
per person
Mar 18 - Mar 22
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Tate House Museum and Thompson's Point are located nearby.
Casco Bay Islands Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Jan 20 - Sat, Jan 24
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$188 Roundtrip, found 9 hours ago
$188
Roundtrip
found 9 hours ago
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Tue, Feb 17 - Tue, Feb 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$204 Roundtrip, found 1 day ago
$204
Roundtrip
found 1 day ago
Thu, Jan 8 - Sat, Jan 10
SEA
Seattle - Tacoma Intl.
PWM
Portland Intl. Jetport
$226 Roundtrip, found 3 days ago
$226
Roundtrip
found 3 days ago
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