Bailey Island Holiday Homes from €160: Search Top House Rentals

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Our top choices for Bailey Island holiday homes

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

1. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

includes taxes & fees

10 Nov - 11 Nov

A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

2. Mid Coast Getaway w/ water views

West Point

Rebecca

includes taxes & fees

12 Nov - 13 Nov

A wooden deck with outdoor seating and string lights.

3. Full sized home

Harpswell

Erika T.

includes taxes & fees

7 Dec - 8 Dec

A bathroom with a window, a sink, a toilet, and a mirror with lights.

4. 2 bedroom w/ expansive water views

West Point

Gregory M.

includes taxes & fees

17 Nov - 18 Nov

A covered porch with a view of a lake and trees.

5. Mere Point Sunrise Views at Eastern Shore!

Brunswick

Michelle S.

includes taxes & fees

16 Nov - 17 Nov

A deck with white railings overlooking a body of water, boats, and a forested shoreline.

6. Captains Watch: A Coastal Escape

West Point

Holly G.

includes taxes & fees

15 Nov - 16 Nov

A lush garden with a hammock, a variety of flowers, and a lake in the background.

7. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

includes taxes & fees

30 Nov - 1 Dec

A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

8. Fantastic Waterfront Views

West Point

Vanessa W.

includes taxes & fees

10 Nov - 11 Nov

A living room with a sofa, armchair, wooden coffee table, and a potted plant.

9. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

includes taxes & fees

11 Nov - 12 Nov

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

10. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

11. Casco Bay Oceanfront Retreat by Everrow

Freeport

"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....

Lisa E.

includes taxes & fees

18 Nov - 19 Nov

A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

12. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Brunswick

Michaela M.

includes taxes & fees

2 Dec - 3 Dec

A backyard with a red Adirondack chair, a barbecue grill, and a wooden treehouse.

13. 1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!

Bath

Esther

includes taxes & fees

24 Nov - 25 Nov

A modern kitchen with a large island, dark cabinetry, and a view of a lake.

14. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

Harpswell

Edwin M.

includes taxes & fees

10 Nov - 11 Nov

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

15. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

A silver convertible car parked in front of a red house with a garden.

16. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

Bath

michael

includes taxes & fees

26 Nov - 27 Nov

A cozy room with wooden flooring, wicker furniture, and a white brick wall.

17. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick

Gary R.

includes taxes & fees

10 Nov - 11 Nov

A two-story white house with a front porch, green shutters, and a covered patio area with chairs.

18. Charming Historic home steps away from downtown

Bath

Holly Y.

includes taxes & fees

17 Nov - 18 Nov

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

19. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

West End

Susan d.

includes taxes & fees

11 Nov - 12 Nov

A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

20. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Georgetown

Palmer M.

includes taxes & fees

10 Nov - 11 Nov

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Learn more about Bailey Island

Hike the Giant's Stairs trail along the rocky coastline for dramatic views of Casco Bay. Seafood lovers shouldn't miss lobster rolls at Cook's Lobster & Ale House on the island's southern tip.

See all hotels in Bailey Island