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Ski Hotels & Resorts in Madeline Island from AU$170

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Check availability on Madeline Island Ski Hotels

Our top choices for Madeline Island ski hotels

2 bars/lounges
Legendary Waters Resort & Casino

Legendary Waters Resort & Casino

Legendary Waters Resort & Casino
2.5 star property
Bayfield
8.0 out of 10, Very good, (406)
"Front desk daytime lady was excellent."
United States
Paul
Legendary Waters Resort & Casino
Boating
The Washburn Inn - On the Lake

The Washburn Inn - On the Lake

The Washburn Inn - On the Lake
2.5 star property
Washburn
8.6 out of 10, Excellent, (1000)
"Very nice accomodations and very friendly staff."
United States
Jayne
The price is AU$183
includes taxes & fees
24 Dec - 25 Dec
The Washburn Inn - On the Lake
Terrace/patio
AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland
2.5 star property
Ashland
7.8 out of 10, Good, (1000)
"Very welcoming, breakfast was good, pool area was clean and well kept. We’ll be staying again. "
United States
Sheila
The price is AU$170
includes taxes & fees
23 Dec - 24 Dec
AmericInn by Wyndham Ashland
Water view
Blue Wave Inn

Blue Wave Inn

Blue Wave Inn
3.0 star property
Ashland
9.8 out of 10, Exceptional, (582)
"Very nice rooms with a beautiful view "
United States
Gerald
Blue Wave Inn
Exterior
Best Western The Hotel Chequamegon

Best Western The Hotel Chequamegon

Best Western The Hotel Chequamegon
3.0 star property
Ashland
8.6 out of 10, Excellent, (1002)
"Clean rooms. Good variety of breakfast options."
United States
Gina
The price is AU$180
includes taxes & fees
24 Dec - 25 Dec
Best Western The Hotel Chequamegon
Studio Suite, 2 Queen Beds, Non Smoking
Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland
2.0 star property
Ashland
8.0 out of 10, Very good, (1001)
"We would definetly stay here again. Very friendly staff."
United States
michael
The price is AU$183
includes taxes & fees
23 Dec - 24 Dec
Super 8 by Wyndham Ashland
Property amenity
St. James Social

St. James Social

St. James Social
4.0 star property
Bayfield
9.4 out of 10, Exceptional, (29)
"Rooms were very clean. Convenient location to walk to restaurants, shopping, etc"
United States
Kelly
St. James Social
Outdoor dining
Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (58)
"Exceeded expectations! The best of both worlds. Rustic, but with all of the amenities you could want. Perfectly private and secluded yet very close to Bayfield. Clean, fresh, and breezy. We loved the fully equipped kitchen, and the screened-in deck. There was no need to eat out. Online check in was easy, and we were able to get help via text when we needed extra towels and when we had a question about the TV. "
United States
Wendy L.
The price is AU$580
includes taxes & fees
12 Jan - 13 Jan 2026
Woodland Chalet @ Brickyard Creek, Bayfield
Property grounds
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Bayfield
9.8 out of 10, Exceptional, (229)
"Location was perfect!"
United States
amy g.
The price is AU$228
includes taxes & fees
15 Dec - 16 Dec
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Beach
Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (52)
"The cabin is extremely clean and well organized with anything you can think of. It's located really close to town, but just outside, so you have peace and quiet. The hosts are very responsive and it made for a perfect trip. "
United States
Matthew
The price is AU$514
includes taxes & fees
30 Dec - 31 Dec
Bayfield Fruit Loop Retreat - Main Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madeline Island Hotel Reviews

Best Western The Hotel Chequamegon

Best Western The Hotel Chequamegon

10/10 Excellent
"We stay here once a year for the Apple Festival. Wouldn’t stay anywhere else. The location is wonderful, staff is always friendly and helpful. The rooms are so cozy and comfortable. It’s always quiet no matter how many people are around. Actually, everyone is alway so nice and chatty. The Landing is a great restaurant, little pricey, but great. We always get a city view. The breakfast is wonderful, so many choices. You can’t go wrong!! "
Beth 3-night trip
Posted 3 months ago
Best Western The Hotel Chequamegon

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