Title: Book the Best Madeline Island Ski Hotels in 2025 | Expedia.ca [Madeline Island Travel Guide](https://expedia.ca/Madeline-Island.dx553248635083902716)[Hotels in Madeline Island](https://expedia.ca/Madeline-Island-Hotels.d553248635083902716.Travel-Guide-Hotels)[Vacation Rentals in Madeline Island](https://expedia.ca/Madeline-Island-Vacation-Rentals.d553248635083902716.Travel-Guide-VacationRentals)[Flights to Madeline Island](https://expedia.ca/Cheap-Flights-To-Madeline-Island.d553248635083902716.Travel-Guide-Flights)[Madeline Island Car Rentals](https://expedia.ca/Car-Rentals-In-Madeline-Island.d553248635083902716.Car-Rental-Guide)[Madeline Island Vacation Packages](https://expedia.ca/Madeline-Island.d553248635083902716.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ceaa419f891d0caf458dbed3d4811504.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Kate Johnson # Find Ski Hotels in Madeline Island, WI ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Madeline Island Ski Hotels Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Madeline Island Ski Hotels ![Boating](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/b643ecc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/3b6c9970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/d1efddee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/ada3163b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Washburn Inn - On the Lake Washburn 8.6/10 Excellent (1032) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee CA $153 CA $171 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Washburn-Hotels-The-Washburn-Inn-On-The-Lake.h459665.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478483/00893773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478483/2fe50a26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478483/7a836732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 King Bed with Sofa bed, Fireplace](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478483/a4a4bf7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legendary Waters Resort & Casino Bayfield 8.0/10 Very good (389) "Always a fun stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SUSANNE CA $138 CA $157 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bayfield-Hotels-Legendary-Waters-Resort-Casino.h61478483.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/610000/601700/601615/8344a88e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/610000/601700/601615/39527225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, fishing](https://images.trvl-media.com/lodging/1000000/610000/601700/601615/3fe3d27d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/610000/601700/601615/a32c6fce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Ashland Ashland 7.8/10 Good (1009) "Very nice hotel. Clean and very helpful courteous staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew A CA $160 CA $179 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Ashland-Hotels-AmericInn-By-Wyndham-Ashland.h601615.Hotel-Information) ![Cottage, Private Bathroom, Lake View | Lounge](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279507/011d7219.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Private Bathroom, Lake View (King Room / Kitchenette)](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279507/80807d8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, Private Bathroom, Lake View | Property entrance](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279507/c8700d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Private Bathroom, Lake View (Guest House) | Private kitchen](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279507/c32e087b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seagull Bay Motel Bayfield 8.8/10 Excellent (261) "We loved our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel CA $154 CA $176 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Bayfield-Hotels-Seagull-Bay-Motel.h13279507.Hotel-Information) ![Water view](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/198db952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/c9a290d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/5acfd4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/a5607e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Wave Inn Ashland 9.8/10 Exceptional (569) "Wonderful accommodations" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $125 CA $140 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Ashland-Hotels-Blue-Wave-Inn.h26680614.Hotel-Information) ![Studio Suite, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/23163c47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/d2d182ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/3afc7a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/8ffb5d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Ashland Ashland 8.0/10 Very good (1019) "We would definetly stay here again. Very friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $162 CA $181 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Ashland-Hotels-Super-8-By-Wyndham-Ashland.h459528.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/2ca0a607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/587e24cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/e33ed132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/826b133f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western The Hotel Chequamegon Ashland 8.6/10 Excellent (1012) "Grand" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn CA $195 CA $218 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ashland-Hotels-Best-Western-The-Hotel-Chequamegon.h5232876.Hotel-Information) ![Basic Cottage, Non Smoking | View from room](https://images.trvl-media.com/lodging/16000000/15040000/15037700/15037664/35b3e2c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/16000000/15040000/15037700/15037664/c97a6619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms, Non Smoking | View from property](https://images.trvl-media.com/lodging/16000000/15040000/15037700/15037664/d5177e25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach](https://images.trvl-media.com/lodging/16000000/15040000/15037700/15037664/16d54f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mission Springs Resort Ashland 9.4/10 Exceptional (66) "The accomodations were lovely and quaint! Everything was clean and comfy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $222 CA $234 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Ashland-Hotels-Mission-Springs-Resort.h15037664.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/97000000/96480000/96477800/96477730/ea7aeadd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King ADA](https://images.trvl-media.com/lodging/97000000/96480000/96477800/96477730/9effa1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner and brunch served, local cuisine](https://images.trvl-media.com/lodging/97000000/96480000/96477800/96477730/cca4adf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/97000000/96480000/96477800/96477730/5b942486.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St. James Social Bayfield 9.4/10 Exceptional (29) "Rooms were very clean. Convenient location to walk to restaurants, shopping, etc" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $321 CA $366 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Bayfield-Hotels-200-Rittenhouse-Ave.h96477730.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/54000000/53630000/53620200/53620159/27c92375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/54000000/53630000/53620200/53620159/f40eb867.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/54000000/53630000/53620200/53620159/30481749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/54000000/53630000/53620200/53620159/b73e9c38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows Bayfield 9.8/10 Exceptional (227) "Very clean and well kept. Even better than the pictures! Excellent location for us, as we were visiting relatives staying at the marina. Would definitely stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pat B. CA $97 CA $210 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Bayfield-Hotels-Apostle-Iss-Gatewaynext-Scenic-Marinasfireplacejacuzzicorner-W-4-Windows.h53620159.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06®ionId=553248635083902716&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Madeline Island Hotel Reviews ![Best Western The Hotel Chequamegon](//images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/2ca0a607_y.jpg) ### 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!! " [](https://expedia.ca/Ashland-Hotels-Best-Western-The-Hotel-Chequamegon.h5232876.Hotel-Information) ![Beautiful home on Madeline Island summer specials](//images.trvl-media.com/lodging/20000000/19110000/19107400/19107343/f9e160d4_y.jpg) ### Beautiful home on Madeline Island summer specials 10/10 Excellent "Beautiful home, lots of space! The in-home ice maker was a nice touch! 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[Bayfield Vacation Rentals](https://www.expedia.ca/Bayfield-Vacation-Rentals.d77465.Travel-Guide-VacationRentals) - [Red Cliff Vacation Rentals](https://www.expedia.ca/Red-Cliff-Vacation-Rentals.d3000408319.Travel-Guide-VacationRentals) - [Book Ski Hotels in Madeline Island on Expedia.com](https://www.expedia.com/Madeline-Island-Hotels-Ski-Hotel.0-0-d553248635083902716-tSkiHotel.Travel-Guide-Filter-Hotels)