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Madeline Island Hotel Guide - Ski Hotels in Madeline Island, Wisconsin

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Check availability on Madeline Island Ski Hotels

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

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 €104
includes taxes & fees
22 Dec - 23 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 €97
includes taxes & fees
28 Dec - 29 Dec
AmericInn by Wyndham Ashland
Terrace/patio
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, (1003)
"Matt at the front desk made us feel welcome after a long trip!"
Canada
Richard
The price is €102
includes taxes & fees
26 Dec - 27 Dec
Best Western The Hotel Chequamegon
Superior Double Room, Private Bathroom, Lake View (Guest House) | Floor plan
Seagull Bay Motel

Seagull Bay Motel

Seagull Bay Motel
2.0 star property
Bayfield
8.8 out of 10, Excellent, (267)
"Room was very clean and well appointed "
United States
Wendy
The price is €129
includes taxes & fees
22 Dec - 23 Dec
Seagull Bay Motel
Standard Room, 1 Queen Bed
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 €91
includes taxes & fees
26 Dec - 27 Dec
Super 8 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, (584)
"Very nice rooms with a beautiful view "
United States
Gerald
Blue Wave Inn
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
Interior
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 €335
includes taxes & fees
1 Jan - 2 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 €132
includes taxes & fees
22 Dec - 23 Dec
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
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
"Clean rooms. Good variety of breakfast options."
Gina 1-night trip
Posted 10 days ago
Best Western The Hotel Chequamegon

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