Deals on vacations and trips to Bailey Island
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Bailey Island flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was $726, price is now $599 per person
$599
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $873, price is now $685 per person
$685
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
This hotel features free WiFi in public areas, a virtual front desk, and self parking. Express check-out is provided and the front desk is staffed around-the-clock.
Blind Tiger Portland - Danforth Street.
West End
Price was $858, price is now $697 per person
$697
per person
Feb 13 - Feb 15
found 22 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast and free WiFi. Luggage storage and concierge services are also provided.
Inn By The Sea
Price was $935, price is now $770 per person
$770
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Portland (PWM)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the playground, onsite laundry facilities, and free supervised childcare. Enjoy the outdoor pool and perks like free valet parking.
Top Bailey Island hotels deals
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Bailey Island ME
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $88 total per night
$88 total
Jan 11 - Jan 12
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy the hot tub and perks like free self parking and a free cruise terminal shuttle.
The Westin Portland Harborview
157 High St Portland ME
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $108 total per night
$108 total
Jan 20 - Jan 21
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $165 total per night
$165 total
Jan 11 - Jan 12
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.
Tru by Hilton Portland Airport Area
369 Maine Mall Road South Portland ME
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $73 total per night
$73 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Portland Harbor Hotel
468 Fore Street Portland ME
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $178 total per night
$178 total
Jan 12 - Jan 13
Total with taxes and fees
This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.
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.
Popular places to visit
Bailey Island Bridge
Find out about the history of Bailey Island when you spend time at Bailey Island Bridge. Stroll along the seaside or seek out the hiking trails.
Land's End Gift Shop
Enjoy an outing to Land's End Gift Shop during your stay in Bailey Island. While you're in the area, find time to visit its shops.
Cobwork Bridge
You can find out about the history of Bailey Island when you stop by Cobwork Bridge. Stroll along the seaside or seek out the hiking trails.
Frequently asked questions
Photos of local treasures
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