
Bailey Island Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Bailey Island Vacation
With one of our vacation packages to Bailey Island, you'll have endless opportunities for relaxation and adventure. There's lots to experience, including its coastal scenery and spectacular views. If sightseeing is on the cards during your trip to Bailey Island, check out popular attractions like Bailey Island Bridge, Lands End Gift Shop and Ragged Island. A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia.
Bailey Island Hotel Deals

The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Apr 5 to Apr 6
CA $134
CA $149 total
Apr 5 - Apr 6
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Just a great place to stay
Reviewed on Mar 10, 2026

Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Mar 24 to Mar 25
CA $106
CA $117 total
Mar 24 - Mar 25
includes taxes & fees
8/10 Very Good! (1,403 reviews)
Nice room with shuttle. Hot tub was not working.
Reviewed on Mar 16, 2026

Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Mar 17 to Mar 18
CA $185
CA $205 total
Mar 17 - Mar 18
includes taxes & fees
9.4/10 Exceptional! (1,602 reviews)
The shuttle to the downtown area is a perk not advertised which is a great option
Reviewed on Mar 16, 2026
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.
Explore a world of travel with Expedia
- Condo Rentals in Bustins Island
- Hotels near Casco Bay
- B&B in Casco Bay Islands
- Chalets in Casco Bay Islands
- Beach Hotel Hotels in Casco Bay Islands
- Cheap Hotels in Casco Bay Islands
- Hotels with Free Breakfast in Casco Bay Islands
- Luxury Hotels in Casco Bay Islands
- Casco Bay Islands Hotels
- Vacation Homes in Casco Bay Islands
- Resorts in Casco Bay Islands
- Villas in Casco Bay Islands
- Aparthotels in Chebeague Island
- B&B in Chebeague Island
- Beach Hotel Hotels in Chebeague Island
- Cheap Hotels in Chebeague Island
- Golf Hotels in Chebeague Island
- Chebeague Island Hotels
- Inns in Chebeague Island
- Cliff Island Hotels
- Farmstay in Cundys Harbor
- Cundys Harbor Hotels
- Townhomes in Cundys Harbor
- Chalets in Great Island
- Guest Houses in Great Island
- Great Island Hotels
- Inns in Great Island
- Lodges in Great Island
- Resorts in Great Island
- B&B in Harpswell
- Castles in Harpswell
- Harpswell Center Hotels
- Cottages in Harpswell
- Guest Houses in Harpswell
- Harpswell Hotels
- Motels in Harpswell
- Hotels near Little John Island Preserve
- Apartments in Littlejohn Island
- Chalets in Littlejohn Island
- Cheap Hotels in Orrs Island
- Luxury Hotels in Orrs Island
- Orrs Island Hotels
- Portland Hotels
- Hostels in Sebasco Estates
- Cheap Hotels in West Point
- West Point Hotels
- Flights to Harpswell
- Flights from Atlanta to Casco Bay Islands
- Flights from Boston to Casco Bay Islands
- Flights from Calgary to Casco Bay Islands
- Flights from Denver to Casco Bay Islands
- Flights from London to Casco Bay Islands
- Flights from Montreal to Casco Bay Islands
- Flights from Seattle to Casco Bay Islands
- Flights from Washington to Casco Bay Islands
- Flights from Edmonton to Casco Bay Islands
- Flights from Buffalo to Casco Bay Islands
- Boothbay Harbor Marina
- Brunswick Vacations
- Cabbage Island
- Casco Bay Islands Vacations
- Visit Casco Bay Islands
- Coastal Maine Botanical Gardens
- Cousins Island Vacations
- Desert of Maine
- Durham Vacations
- East End Beach
- Freeport Vacations
- Great Diamond Island Vacations
- Great Island Vacations
- Visit Harpswell
- Hermit Island Vacations
- Higgins Beach
- Hunnewell Beach
- Josephine Newman Audubon Sanctuary
- Ll Bean Flagship Store
- Long Island Vacations
- Maine Mall
- Mclellan-Sweat Mansion
- Visit Orrs Island
- Popham Beach State Park
- Portland Head Light
- Portland Museum of Art
- Portland Vacations
- Scarborough Beach State Park
- Scarborough Vacations
- South Portland Vacations
- State Theatre
- Westbrook Vacations
- Windham Vacations
- Bidvest Rental Cars in Casco Bay Islands
- Budget Rental Cars in Harpswell
- Car rental Chebeague Island
- Hertz Rental Cars in Harpswell Center
- Island Car Rentals Rental Cars in Casco Bay Islands
- Kk Leisure Rental Cars in Casco Bay Islands
- National Car Rental Rental Cars in Great Island
- Thai Cars Rental Cars in Casco Bay Islands
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







