Search Deals onBailey Island Vacation Packages
Bailey Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Best Western Freeport Inn
Save 100% on your flight
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this 3-star hotel in Freeport. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha are located nearby.
Portland Harbor Hotel
Save 100% on your flight
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 State Theatre and Thompson's Point are located nearby.
Casco Bay Inn
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha are located nearby.
Chebeague Island Inn
Save 100% on your flight
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Dormir
per person
Jul 27 - Aug 2
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sebago Lake and Seacoast Adventure are located nearby.
The Kennebunk Inn
per person
Aug 7 - Aug 10
found 18 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Portland (PWM)
Stay at this hotel in Kennebunk. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
Blind Tiger Portland – Carleton Street
Save 100% on your flight
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Portland (PWM)
Stay at this 3.5-star B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions State Theatre and Thompson's Point are located nearby.
Ogunquit River Inn & Suites
per person
Aug 7 - Aug 10
found 18 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Portland (PWM)
Stay at this 3-star business-friendly hotel in Ogunquit. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ogunquit Beach and Moody Beach 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.
Mon, Oct 6 - Thu, Oct 9
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$162 Roundtrip, just found
$162
Roundtrip
just found
Tue, Aug 5 - Wed, Aug 13
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Fri, Oct 3 - Tue, Oct 7
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
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