Cheap Vacations in Bailey Island

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Flight deals to Bailey Island

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Jan 31 - Fri, Feb 6
MCO
Orlando
PWM
Portland
$166 Roundtrip, found 4 days ago
$166
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Jan 31 from Orlando to Portland, returning Fri, Feb 6, priced at $166 found 4 days ago
Wed, Jan 28 - Wed, Feb 4
DCA
Washington
PWM
Portland
$184 Roundtrip, found 5 days ago
$184
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Wed, Jan 28 from Washington to Portland, returning Wed, Feb 4, priced at $184 found 5 days ago
Tue, Oct 20 - Tue, Oct 27
PHL
Philadelphia
PWM
Portland
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Oct 20 from Philadelphia to Portland, returning Tue, Oct 27, priced at $222 found 3 days ago

Top rated hotels for your Bailey Island vacation

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island ME
0.17 mi from city center
Get rates
With a stay at this vacation home in Bailey Island, you'll be on the beach, just a 1-minute walk from Casco Bay and 14 minutes by foot from Mackerel Cove.
Kitchen
Washer
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road South Portland ME
Free Cancellation
Reserve now, pay when you stay
18.56 mi from city center
$74 nightly
The price is $81 total per night
$81 total
Dec 15 - Dec 16
Total with taxes and fees
With a stay at Tru by Hilton Portland Airport Area in South Portland, you'll be near the airport, just steps from Maine Mall and a 3-minute drive from Nonesuch River Golf Club.
Breakfast included
Free airport shuttle
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
14.2 mi from city center
$157 nightly
The price is $174 total per night
$174 total
Dec 16 - Dec 17
Total with taxes and fees
A stay at Portland Harbor Hotel places you in the heart of Portland, steps from Casco Bay and 3 minutes by foot from Cross Insurance Arena.
Pet friendly
Free WiFi
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See all available properties in Bailey Island
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.