Baileys Harbor Holiday Homes from £200: Search Holiday Homes in Baileys Harbor

An aerial view of a coastal island with a mix of residential areas, green spaces, and rocky coastlines.

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Our top choices for Baileys Harbor holiday homes

A loft-style living space with a high ceiling, a wooden staircase, a patterned sofa, a grey couch, and a small table with a lamp.

1. Dog Friendly home in Baileys Harbor near Cana Island Lighthouse

Baileys Harbor

includes taxes & fees

27 Oct - 28 Oct

A two-story building with a wooden staircase leading to a balcony.

2. Spectacular Sunsets at 3 BR Classic Farm House

Egg Harbor

Nick S.

A two-story house with a wrap-around porch, a turret, and a front door with an American flag.

3. Private 3BR Gem on 2.5 Wooded Acres- Close to All

Sister Bay

Andrew L.

includes taxes & fees

21 Oct - 22 Oct

A dining area with a round glass table and two chairs, a potted plant, and a view of a street through a window with blinds.

4. Cozy Door County home with detached yoga room- short walk from Potawatomi Park

Sturgeon Bay

Suzanne H.

includes taxes & fees

13 Oct - 14 Oct

A modern living room with a stone fireplace, large windows, and a cozy seating area.

5. Cedar & Glass | Modern Architectural Retreat

Fish Creek

katherine k.

includes taxes & fees

21 Oct - 22 Oct

A modern living room with a stone fireplace, a large flat-screen TV mounted on a wall, a comfortable leather sofa, and a wooden coffee table.

6. Shore Suite | Downtown Fish Creek ~ Dog-friendly

Fish Creek

The M.

includes taxes & fees

19 Oct - 20 Oct

An aerial view of a house surrounded by dense forest, with a clear path leading to the entrance.

7. Wooded Sister Bay Retreat, Walk to town, Firepit

Sister Bay

Brad V.

includes taxes & fees

19 Oct - 20 Oct

A backyard with two blue Adirondack chairs, a fire pit, and a house in the background.

8. Walk to Downtown! Wooded 4BR Sister Bay Home

Sister Bay

Nicole H.

includes taxes & fees

4 Oct - 5 Oct

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Top Baileys Harbor Hotel Reviews

Cherry Hills Golf & Lodge

10/10 Excellent

"Microwave breakfast"

Coachlite Inn

10/10 Excellent

"Our room was quite large and well appointed, and the bed was very comfortable. Location was good - less than 5 min to the main dining/shopping area. We didn't use the offered breakfast except for coffee/juice, but there was a decent offering of bread,pastries, cereal, hard boiled eggs, and yogurt. No hot items are offered. The only complaint is that the wi-fi was terrible - it worked better on our phones but would not hold a connection on our tablets. Overall a very good stay - I would definitely stay there again."