Bailey Island Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Bailey Island

3-bdrm house in beautiful Boothbay! A perfect location for relaxing getaways!

Boothbay ME

With a stay at this chalet in Boothbay, you'll be within a 10-minute drive of Coastal Maine Botanical Gardens and Knickerbocker Lake.

Kitchen

Washer

Charming 110-year former Inn 10' from the Ocean!

South Portland ME

With a stay at this vacation home in South Portland (Willard Beach), you'll be within a 15-minute drive of Cross Insurance Arena and Thompson's Point.

Kitchen

Washer

Nature with in-town living that feels a world away. May-June-July special!!!

Portland ME

With a stay at this vacation home, you'll be centrally located in Portland, within a 5-minute drive of Maine Mall and Thompson's Point.

Kitchen

Washer

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME

Located in Harpswell, this vacation home is a 1-minute drive from Casco Bay and 7 minutes from Androscoggin River.

Camp Forever cottage

Harpswell ME

$333 nightly

$363 total

Sep 11 - Sep 12

Total with taxes and fees

Located in Harpswell, this vacation home is by the ocean, within a 15-minute drive of Casco Bay and Bailey Island Bridge.

Kitchen

Free WiFi

Full sized home

Harpswell ME

$339 nightly

$369 total

Sep 22 - Sep 23

Total with taxes and fees

With a stay at this vacation home in Harpswell, you'll be by the sea, just steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.

Backyard Paradise

Portland ME

With a stay at this vacation home, you'll be centrally located in Portland, within a 5-minute drive of Maine Mall and Thompson's Point.

Pool

Kitchen

NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.

Peaks Island ME

With a stay at this vacation home in Peaks Island, you'll be on the waterfront, just steps from Casco Bay and a 4-minute drive from Umbrella Cover Museum.

Shady Potts Point Cottage Cooled by Ocean Breezes

Harpswell ME

With a stay at this vacation home in Harpswell, you'll be by the sea, just steps from Casco Bay and a 3-minute drive from Ash Cove Pottery.

Kitchen

Pet friendly

Clean, Cozy, and Professional Waterfront Home- minutes to Portland

Falmouth ME

When you stay at this vacation home in Falmouth, you'll be on the waterfront, within a 15-minute drive of Cross Insurance Arena and Thompson's Point.

Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets

Phippsburg ME

Located in Phippsburg, this vacation home is on the waterfront, within a 15-minute drive of Casco Bay and Kennebec River.

Doubling Point Cottage - Water Views, Dog Friendly

Bath ME

With a stay at this vacation home in Bath, you'll be steps from Casco Bay and a 2-minute drive from Maine Maritime Museum.

Don't see what you're looking for?

See all available properties in Bailey Island

View all properties

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.