Bailey Island Cottages
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
Cottages in Bailey Island
Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!
Orr's Island ME
With a stay at this cottage in Orrs Island, you'll be by the sea, just steps from Casco Bay and a 4-minute drive from Bailey Island Bridge.
Kitchen
Outdoor Space
Enjoyable 1-bedroom rustic cottage in Southport.
Southport ME
With a stay at this cottage in Southport, you'll be on the waterfront, within a 15-minute drive of Coastal Maine Botanical Gardens and Hendricks Hill Museum.
Kitchen
Pet friendly
Come and enjoy our Boothbay Cottage
Boothbay Harbor ME
With a stay at this cottage in Boothbay Harbor, you'll be on the beach, within a 15-minute drive of Coastal Maine Botanical Gardens and Linekin Bay.
Hot Tub
Kitchen
Cozy Year-round House right outside Portland Maine on Highland Lake.
Windham ME
Located in Windham, this cottage is on the waterfront, within a 10-minute drive of MAGAN Trailhead and Mercy Primary Care.
Kitchen
Washer
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
Harpswell ME
Located in Harpswell, this cottage is by the sea, a 1-minute drive from Casco Bay and 6 minutes from Mitchell Field.
Kitchen
Pet friendly
Brand New CozyCottage 1bdrm with "ADD ON" 2bdrm Cottage nextdoor! BoothbayHarbor
Boothbay Harbor ME
With a stay at this cottage in Boothbay Harbor, you'll be within a 10-minute drive of Coastal Maine Botanical Gardens and Opera House at Boothbay Harbor.
Kitchen
Air conditioning
Popham Beach Direct Oceanfront Cottage Steps to the sand
Phippsburg ME
When you stay at this cottage in Phippsburg, you'll be on the beach, just steps from Casco Bay and Popham Beach State Park.
Kitchen
Pet friendly
WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND
WINDHAM ME
Located in Windham, this cottage is on the waterfront, within a 15-minute drive of Mercy Primary Care and MAGAN Trailhead.
Kitchen
Pet friendly
Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME
Georgetown ME
Located in Georgetown, this cottage is by the ocean, within a 5-minute drive of Reid State Park and Georgetown Historical Society.
Kitchen
Washer
Waterfront Cottage
Brunswick ME
Located in Brunswick, this cottage is by the ocean, a 1-minute drive from Casco Bay and 5 minutes from Thomas Point Beach.
Kitchen
Washer
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.
Bailey Island Cottages essential information
Accommodation | 183 Cottages |
|---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Classic Orr’s Island, Maine Cottage, sleeps 4, 1 Bath, Stunning ocean views!, Enjoyable 1-bedroom rustic cottage in Southport., Come and enjoy our Boothbay Cottage, Cozy Year-round House right outside Portland Maine on Highland Lake., Thorburn - Experience a classic ME vacation at this beautiful summer cottage, Brand New CozyCottage 1bdrm with "ADD ON" 2bdrm Cottage nextdoor! BoothbayHarbor, Popham Beach Direct Oceanfront Cottage Steps to the sand, WATERFRONT ON HIGHLAND LAKE. LESS THAN 30 MINUTES TO PORTLAND, Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME, Waterfront Cottage, Stunning Ocean Views, newly renovated cottage-close to preserves, trails, and Harpswell Beaches, Quaint Retro Ash Cove Cottage |