Skip to content

Holiday rentals in Madeline Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Madeline Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cozy Downtown Flat with Historic Waterfront Views
Entire townhouse · 4 guests · 2 beds · 1 bathroom
Cozy Downtown Flat with Historic Waterfront ViewsWhile nestled into this cozy flat enjoy a morning cup of coffee as you watch boats depart from the historic waterfront. Leave the car behind and wander historic streets discovering quaint shops and good eats. Venture a little further and find the start to the 300 acre Big Ravine Preserve trails. End the day at Washington Avenue Beach watching the sun set over the islands. This flat welcomes you in and provides easy access to all the charms Bayfield offers.
Bayfield Fruit Loop Retreat - Main Cottage
Entire cottage · 3 guests · 2 beds · 1 bathroom
Bayfield Fruit Loop Retreat - Main CottageWelcome to the Bayfield Fruitloop Retreat, featuring a beautiful "Main Cottage" nestled in 7 acres of woods in Bayfield, WI. The property allows you to savor a peaceful and quiet northwoods experience but still minutes from several attractions and downtown Bayfield. The property is conveniently located just 5 minutes' drive or 2.5 miles from the center of downtown Bayfield. Located right on country Hwy J, a starting point for a self-guided tour around the city of Bayfield where an exploration of local food culture begins of several family apple orchards, fruit farms, and wineries, called the Bayfield fruit loop, and the origin of our property name. County Hwy J right out of our driveway also allows access for ATV & snowmobiles to get to many of the local routes and surrounding trails. Enjoy exploring Lake Superiors South Shore with various hiking trails, mountain biking, public beaches and state parks. Take the Bayfield Ferry to Madeline Island by foot of car. See the Apostle Islands sea caves through kayaking or guided site seeing cruises (seasonal) there is so much to explore.
Sputnik Apartment, Beautiful Bayfield !
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bathroom
Sputnik Apartment, Beautiful Bayfield !Welcome to the Sputnik ! Beautifully appointed apartment just two blocks from downtown and the Ferry dock . Private entrance , private porch , private fire pit and grill station . Full kitchen , bath , living area and bedroom . Work station , closet and window view breakfast nook .

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Madeline Island holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Madeline Island

  1. Entire cottage
  2. Bayfield
Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods
$208 SGD per night
SUPERHOST
  1. Entire cottage
  2. Bayfield
Updated Cozy Cottage Above Brickyard Creek
$264 SGD per night
SUPERHOST
  1. Entire residential home
  2. La Pointe
Wonderful Family Log Cabin
$357 SGD per night
SUPERHOST
  1. Private room
  2. La Pointe
#1 Lakeside... The other suite
$122 SGD per night
SUPERHOST
  1. Entire rental unit
  2. Bayfield
Island View Retreat
$232 SGD per night
SUPERHOST
  1. Tiny house
  2. Bayfield
Modern Nest w/Meals, Sauna, Yoga Wild Rice Retreat
$424 SGD per night
SUPERHOST
  1. Treehouse
  2. Bayfield
Boulderridge Treehouse
$409 SGD per night
SUPERHOST
  1. Entire apartment
  2. La Pointe
Sheila's Downtown Condo
$150 SGD per night
SUPERHOST
  1. Private room
  2. Bayfield
Lodge by the Lake, Pine Cove
$103 SGD per night
SUPERHOST
  1. Entire cabin
  2. Bayfield
Nordic Modern | White Pine Chalet @ BrickyardCreek
$349 SGD per night
SUPERHOST
  1. Private room
  2. Bayfield
Lodge by the Lake, Eagle's Nest
$116 SGD per night
SUPERHOST
  1. Hotel room
  2. Bayfield
Queen-Lake View-Private Bathroom-Queen/Lake View(Upper)
$160 SGD per night