Baileys Harbor Vacation Rentals

Our Favorite Vacation Rentals in Baileys Harbor

  • Cana Island Lighthouse Water Front Family Retreat
     Country House
    Booking.com
    From
    $575
  • Door County Cabin in the Woods, Baileys Harbor
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $288
  • Bailey's Harbor Cabin Near Kangaroo Lake
    NiceCottage
    HolidayLettings
    From
    $223
  • Egg Harbor Log Cabin, Door County
    Good2br Home/Apartment
    HolidayLettings
    From
    $288
  • Egg Harbor Home w/Deck on 2 Acres - 12 Min to Lake
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $409
  • Fish Creek Condo/Town Home at Brook Point, Door County
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $288
  • Sister Bay Cottage
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $289
  • Blue Harbor Lodge (DC2) Door County, WI.
    Good4br Home/Apartment
    HolidayLettings
    From
    $345

Check prices for these upcoming dates

Baileys Harbor Vacation Rentals with a Pool

  • Newly Updated Lake View Escape
    ExcellentHome/Apartment
    Airbnb
    From
    $146
  • Homestead Park House
    Excellent5br Home/Apartment
    Airbnb
    From
    $561
  • Peninsula Parkview Sunset Meadow Whirlpool Cottage
    GoodHome/Apartment
    Airbnb
    From
    $208
  • Condo A6 at Evergreen Hill - Park Lover's location
    Good2br Home/Apartment
    Airbnb
    From
    $123

Baileys Harbor Vacation Rentals with Wi-Fi

  • Baileys Harbor Yellow Home with a View
    Excellent3br Home/Apartment
    Airbnb
    From
    $192
  • Door County Dreaming
    Excellent3br Home/Apartment
    Airbnb
    From
    $150
  • South Lane Cottage #1
    Excellent2br Home/Apartment
    Airbnb
    From
    $136
  • Historic Baileys Harbor Home on the Water
    Good6br Home/Apartment
    Airbnb
    From
    $777

Baileys Harbor Pet-Friendly Vacation Rentals

  • NEW! ‘The Landmark’ Resort Condo - 1 Mi to Beach!
     2br Home/Apartment
    HolidayLettings
    From
    $200
  • Updated Home w/Deck, 2 Mi to Sister Bay Beach
     4br Cottage
    HolidayLettings
    From
    $350
  • Water Front Home in Baileys Harbor on the quiet side of beautiful Door County
    Okay6br Home/Apartment
    HolidayLettings
    From
    $537
  • North unit Baileys Harbor Secluded Cozy Cabin
     Cottage
    HolidayLettings
    From
    $214

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
40° -20°
2
38° -12°
2
51° -11°
1
62° 23°
3
81° 32°
2
83° 36°
2
88° 52°
2
83° 52°
2
77° 46°
4
73° 29°
4
50° 11°
2
43° -1°
2
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Baileys Harbor. The hottest month in Baileys Harbor is June, when temperatures peak at 88 ˚F. The coolest month is December, when temperatures drop to -20 ˚F. The wettest month in Baileys Harbor is April with 4.43 inches of rain, while the driest month is October with 1.2 inches of rain.

What Expert Travelers Think

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    Max Hobbs
    Max HobbsLTL Mandarin School
  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE

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