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 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-09-26&endDate=2025-09-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Madeline Island Ski Hotels ## Our top choices for 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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/3b6c9970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Washburn Inn - On the Lake Washburn 8.6/10 Excellent (1032) "Cozy and hosts were very friendly " CA $138 CA $154 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) ![Exterior](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478483/ef5f8b81.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 (366) "Excellent location." CA $249 CA $284 total includes taxes & fees Sep 28 - Sep 29 [](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) ![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) ![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) ![2 indoor pools](https://images.trvl-media.com/lodging/1000000/610000/601700/601615/94b5fe3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AmericInn by Wyndham Ashland Ashland 7.8/10 Good (1005) "Excellent for families! " CA $193 CA $216 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ashland-Hotels-AmericInn-By-Wyndham-Ashland.h601615.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/8ffb5d06.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) ### Super 8 by Wyndham Ashland Ashland 8.0/10 Very good (1017) "Good stay for overnight in a busy resort area." CA $149 CA $167 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ashland-Hotels-Super-8-By-Wyndham-Ashland.h459528.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) ![Property amenity](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/52adc64e.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 (558) "Clean, quiet, and friendly. Great view on the lake" CA $173 CA $194 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Ashland-Hotels-Blue-Wave-Inn.h26680614.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) ![Fireplace](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/f08d5560.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) ### Best Western The Hotel Chequamegon Ashland 8.6/10 Excellent (1009) "The view was amazing and the building had great character " CA $249 CA $279 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ashland-Hotels-Best-Western-The-Hotel-Chequamegon.h5232876.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/72000000/71610000/71607600/71607554/b21cd706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/72000000/71610000/71607600/71607554/1f7fdb4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71610000/71607600/71607554/b8ab4c9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71610000/71607600/71607554/89acf76c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayfield Fruit Loop Retreat - Main Cottage Bayfield 10/10 Exceptional (51) "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. " CA $419 CA $537 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Bayfield-Hotels-Bayfield-Fruit-Loop-Retreat-Main-Cottage.h71607554.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51870000/51868300/51868228/696abff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51870000/51868300/51868228/f3ad3563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/52000000/51870000/51868300/51868228/ec156335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/52000000/51870000/51868300/51868228/6e52b8b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Shore Home with private dock and large deck--1 mile from Bayfield Bayfield 10/10 Exceptional (108) "The home and location were perfect for our friends weekend! Views of Lake Superior are seen from every room. We enjoyed the comfortable beds and appreciated the host’s attention to detail. Monica was very easy to communicate with and would love to return for another stay!" CA $417 CA $845 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bayfield-Hotels-Spacious-Home-On-Lake-Superior-1-Mile-From-Bayfield.h51868228.Hotel-Information) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/72000000/71610000/71609100/71609091/42a94261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/72000000/71610000/71609100/71609091/3d2b80d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71610000/71609100/71609091/d4594d6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71610000/71609100/71609091/dcc15aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods Bayfield 10/10 Exceptional (39) "We had a wonderful stay! The cabin was stocked with anything you would need, vey clean, and excellent accommodations! Would love to stay again next time we visit!" [](https://www.expedia.ca/Bayfield-Hotels-Bayfield-Fruit-Loop-Retreat-Rock-Garden-Cottage-In-The-Woods.h71609091.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=2025-10-09&endDate=2025-10-10®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 "Easy check in, friendly staff even with the construction." [](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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