Baileys Harbor Vacation Rentals

Our Favorite Vacation Rentals in Baileys Harbor

  • Water Front Home in Baileys Harbor on the quiet side of beautiful Door County
     6br Home/Apartment
    HolidayLettings
    From
    $896
  • Bailey's Harbor Cabin Near Kangaroo Lake
    NiceCottage
    HolidayLettings
    From
    $222
  • Egg Harbor Home w/Deck on 2 Acres - 12 Min to Lake
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $427
  • Leaf House Door County
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $283
  • Blue Harbor Lodge (DC2) Door County, WI.
    Good4br Home/Apartment
    HolidayLettings
    From
    $471
  • NEW! Landmark Resort Condo w/ Spectacular Views!
     2br Home/Apartment
    HolidayLettings
    From
    $291
  • A True Farmhouse Experience
    Excellent2br Home/Apartment
    Airbnb
    From
    $133
  • ♦♦Relaxing, Historic and Hip Havngård House♦♦
    Excellent3br Home/Apartment
    Airbnb
    From
    $294

Check prices for these upcoming dates

Baileys Harbor Vacation Rentals with a Pool

  • Sleeper Bunk House
    GoodHome/Apartment
    Airbnb
    From
    $116
  • Apartment C7
     3br Home/Apartment
    Airbnb
    From
    $141
  • Peaceful getaway in Door county. Save $$ in Sept.
    Excellent3br Home/Apartment
    Airbnb
    From
    $424
  • Newly Updated Lake View Escape
    ExcellentHome/Apartment
    Airbnb
    From
    $146

Baileys Harbor Vacation Rentals with Wi-Fi

  • Modern Hygge Farmhouse - Baileys Harbor/Fish Creek
     4br Home/Apartment
    Airbnb
    From
    $503
  • Eclectic Modern Farmhouse in Baileys Harbor
    Excellent5br Farmhouse
    Airbnb
    From
    $677
  • Foxlea Guest House in Fish Creek
    Excellent4br Home/Apartment
    Airbnb
    From
    $538
  • Waterfront Views in Moonlight Bay
    Excellent3br Home/Apartment
    Airbnb
    From
    $494

Baileys Harbor Pet-Friendly Vacation Rentals

  • Carraig Dale Cottage - A Peaceful Oasis
     3br Home/Apartment
    Airbnb
    From
    $565
  • Perfect for weekend getaways and family reunions
     Home/Apartment
    Airbnb
    From
    $689
  • Sister Bay Eclectic Cottage
    Excellent3br Home/Apartment
    Airbnb
    From
    $408
  • Downtown Sunset View Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $172

Bailey's Harbor Wisconsin Travel Guide Travel Guide

Tucked away on the eastern shore of the Door County Peninsula in Wisconsin, Baileys Harbor is a hidden gem when it comes to vacations. With over 6,000 acres of public lands prime for trailblazing and connecting with nature, it's no wonder Baileys Harbor is known as the prettiest town in Wisconsin.

Things to Do in Bailey's Harbor Wisconsin Travel Guide

Top attractions include Cana Island Lighthouse, Door County's most photographed lighthouse, and the Ridges Sanctuary, a 1,600 acre national landmark and nature preserve great for bird watching. For drinks, visit Door County Brewing Co., a landmark, family-owned brewery that features craft brews named after local characters, locations and events.

Best Time to Visit Bailey's Harbor Wisconsin Travel Guide

The best times to visit Baileys Harbor are in May and June, when annual festivities commence. In May, the town hosts its annual Blessing of the Fleet, an event that pays tribute to past and present fishing and maritime industries in the town, and the annual Ridges Sancutary Festival of Nature, which features bird watching and other festivitie. Meanwhile, in June, the town hosts the Door County Maritime Museum's Lighthouse Festival, which includes a tour of three of the town's lighthouses, and the Door County Beer Festival and Peninsula Century Spring Class, a beer festival and classic bicycle ride.

Price and Availability in Baileys Harbor

Most expensive
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The cheapest day to stay at a vacation rental in Baileys Harbor tends to be Monday, while the most expensive day tends to be Sunday. Vacation homes in Baileys Harbor tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Baileys Harbor is in August, while the cheapest month is in November. The most popular time to book a vacation rental in Baileys Harbor is in the high season in July. Baileys Harbor has its low season in February, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Baileys Harbor

Rainy days
85 º38
1
71 º28
2
46 º15
2
42 º14
1
48 º-7
1
49 º-6
1
47 º10
1
62 º12
2
87 º33
3
88 º42
4
83 º51
3
86 º47
2
Sep
Oct
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Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Baileys Harbor. The hottest month in Baileys Harbor is July, when temperatures peak at 88 ˚F. The coolest month is December, when temperatures drop to -7 ˚F. The wettest month in Baileys Harbor is July with 3.74 inches of rain, while the driest month is October with 0.74 inches of rain.

What Expert Travelers Think

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    Kaelin
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    Daniella Flores
    Daniella FloresILIKETODABBLE
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad

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