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 3 days ago
$166
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jan 31 from Orlando to Portland, returning Fri, Feb 6, priced at $166 found 3 days ago
Wed, Jan 28 - Wed, Feb 4
DCA
Washington
PWM
Portland
$184 Roundtrip, found 4 days ago
$184
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Wed, Jan 28 from Washington to Portland, returning Wed, Feb 4, priced at $184 found 4 days ago
Tue, Oct 20 - Tue, Oct 27
PHL
Philadelphia
PWM
Portland
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Tue, Oct 20 from Philadelphia to Portland, returning Tue, Oct 27, priced at $222 found 2 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
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
15.79 mi from city center
$84 nightly
The price is $93 total per night
$93 total
Dec 7 - Dec 8
Total with taxes and fees
With a stay at Clarion Hotel Portland Airport ME in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition Building.
Pool
Hot Tub
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
14.62 mi from city center
$98 nightly
The price is $108 total per night
$108 total
Dec 21 - Dec 22
Total with taxes and fees
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
Spa
Pet friendly
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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.