Baileys Harbor Vacation Rentals

Check prices for these upcoming dates

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
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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
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
40° -20°
2
38° -12°
2
51° -11°
1
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Rainy days

This climate histogram shows you the weather patterns in Baileys Harbor. The warmest months in Baileys Harbor are June and July, when temperatures reach 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

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from

    ArtMatters.Info
    ArtMatters.InfoArtMatters.Info

Destinations near Baileys Harbor

  • Wisconsin Dells1,634 Properties
  • Oshkosh1,075 Properties
  • Lake Delton1,062 Properties
  • St Germain827 Properties
  • Eagle River774 Properties
  • Green Bay606 Properties
  • Sturgeon Bay600 Properties
  • Appleton576 Properties
  • Hayward532 Properties
  • Minocqua492 Properties
  • Milwaukee463 Properties
  • Lake Geneva439 Properties
  • Eau Claire423 Properties
  • Egg Harbor409 Properties
  • Sheboygan371 Properties
  • Madison361 Properties
  • Wauwatosa316 Properties
  • Sister Bay315 Properties
  • Brookfield287 Properties
  • Bayfield242 Properties
  • Wausau233 Properties
  • Fish Creek218 Properties
  • Cable201 Properties
  • La Crosse195 Properties
  • Plymouth178 Properties
  • Racine164 Properties
  • Rhinelander161 Properties
  • Baraboo154 Properties
  • Fond du Lac124 Properties
  • Ephraim116 Properties
  • Green Lake51 Properties
  • Black River Falls40 Properties