Search Deals onBailey Island Vacation Packages
Bailey Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
per person
Feb 14 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 Maine Mall and Cross Insurance Arena are located nearby.
The Weldon Hotel
Save 100% on your flight
per person
Feb 14 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 4-star aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Maine Mall and Victoria Mansion are located nearby.
River View Resort
per person
Mar 6 - Mar 11
found 2 hours ago
Roundtrip flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this motel in Bethel. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Sunday River and Bethel Pathway are located nearby.
Hilton Garden Inn Freeport Downtown
per person
Jan 30 - Feb 6
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Freeport. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
Inn By The Sea
per person
Mar 6 - Mar 11
found 2 hours ago
Roundtrip flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 4-star beach 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 – Carleton Street
per person
Mar 6 - Mar 11
found 2 hours ago
Roundtrip flight included
Milwaukee (MKE) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and daily housekeeping. Popular attractions Maine Mall and Neal S. Dow House are located nearby.
The Harraseeket Inn & Event House
per person
Feb 14 - Feb 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this 3.5-star business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
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.
Fri, Apr 4 - Mon, Apr 7
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Mon, Mar 31 - Tue, Apr 1
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$127 Roundtrip, found 3 days ago
$127
Roundtrip
found 3 days ago
Mon, Jan 20 - Fri, Jan 24
TTN
Mercer
PWM
Portland Intl. Jetport
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
Sun, Jan 12 - Mon, Jan 13
PHL
Philadelphia Intl.
PWM
Portland Intl. Jetport
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
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