![](https://forever.travel-assets.com/flex/flexmanager/images/2020/11/06/TVLY-MSJE-DTG-Hero-Image.jpg?impolicy=fcrop&w=900&h=225&q=mediumHigh)
Deals on vacations and trips to Bailey Island
Save when you book Bailey Island package deals
Top Bailey Island hotels deals
![Casco Bay Hotel, Ascend Hotel Collection](https://images.trvl-media.com/lodging/2000000/1090000/1085000/1084959/94dd4950_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Casco Bay Hotel, Ascend Hotel Collection
80 John Roberts Rd., South Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $116 per night
$116
per night
Jun 24 - Jun 25
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Business travelers can take advantage of the free WiFi in public areas. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.
Breakfast included
Free airport shuttle
![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/c479d2b6_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
The Westin Portland Harborview
157 High St, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $237 per night
$237
per night
Jun 30 - Jul 1
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. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.
Spa
Pet friendly
![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/c27bf7ea_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Portland Harbor Hotel
468 Fore Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $296 per night
$296
per night
Jun 24 - Jun 25
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.
Pet friendly
Free WiFi
![Canopy by Hilton Portland Waterfront](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/2dbce532_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Canopy by Hilton Portland Waterfront
9 Center Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $359 per night
$359
per night
Jun 23 - Jun 24
This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Free WiFi
![Comfort Inn Airport](https://images.trvl-media.com/lodging/1000000/30000/27100/27041/c0611e0b_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Comfort Inn Airport
90 Maine Mall Rd, South Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $113 per night
$113
per night
Jun 24 - Jun 25
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and a free airport shuttle. Traveling on business? Take advantage of the express check-out, laundry service, and free train station pick-up. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Free airport shuttle
![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/d87c36dc_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Portland Regency Hotel & Spa
20 Milk Street, Portland, ME
Free Cancellation
Reserve now, pay when you stay
The price is $289 per night
$289
per night
Jul 2 - Jul 3
A full-service spa, a spa 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.
Hot Tub
Spa
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
4.5/5(9 reviews)
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.
Photos of local treasures
Browse Bailey Island vacation photos for more inspiration
![Bailey Island showing general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/265000/265181-Central-Coast-Maine.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)
Frequently asked questions
Top all inclusive vacation packages with airfare
Book a vacation to Bailey Island
Most popular
Hotels
Hotels in Boothbay HarborHotels in Bar HarborHotels in RocklandHotels in AuburnBeach Resorts & Hotels in Old Orchard BeachHotels in BangorHotels in CamdenHotels in OgunquitHotels in KennebunkBeach Resorts & Hotels in OgunquitHotels in PortlandHotels in AugustaHotels in YorkHotels in FreeportHotels in SacoHotels in KennebunkportHotels in BrunswickHotels in WatervilleHotels in EllsworthBeach Resorts & Hotels in York BeachHotels in Wells