Search Deals onBailey Island Vacation Packages
Bailey Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

SpringHill Suites by Marriott Freeport Brunswick
per person
Apr 27 - May 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Bradbury Mountain State Park and Wilbur's of Maine Chocolate Confections are located nearby.

Waldo Emerson Inn
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 3-star B&B in Kennebunk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions Wedding Cake House and Kennebunk Dog Park are located nearby.

Chebeague Island Inn
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
Stay at this 4-star beach hotel in Chebeague Island. Enjoy free WiFi, breakfast (surcharge), and a free ferry terminal shuttle. Popular attractions Little John Island Preserve and Winslow Memorial Park are located nearby.

InnSeason Resorts The Falls at Ogunquit
per person
Apr 27 - May 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Moody Beach and Ogunquit Beach are located nearby.

Inn By The Sea
Save 100% on your flight
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
Stay at this 4-star 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.

Portland Harbor Hotel
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Portland (PWM)
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.

AWOL Kennebunkport
per person
Apr 27 - May 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 3-star 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 Kennebunkport Village Green and W. Robert Paine Gallery are located nearby.

Blind Tiger Portland - Danforth Street.
Save 100% on your flight
per person
May 14 - May 18
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Thompson's Point and Maine Mall are located nearby.
Bailey Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Bailey Island Vacation Packages 5-7 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.

Sat, Apr 19 - Sat, Apr 26
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$89 Roundtrip, found 3 days ago
$89
Roundtrip
found 3 days ago

Wed, May 21 - Tue, May 27
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago

Wed, May 7 - Wed, May 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago

Tue, May 13 - Tue, May 20
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
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