Title: Book the Best Chequamegon Bay Ski Hotels in 2025 | Expedia.ca [Chequamegon Bay Travel Guide](https://expedia.ca/Chequamegon-Bay.dx6141305)[Hotels in Chequamegon Bay](https://expedia.ca/Chequamegon-Bay-Hotels.d6141305.Travel-Guide-Hotels)[Vacation Rentals in Chequamegon Bay](https://expedia.ca/Chequamegon-Bay-Vacation-Rentals.d6141305.Travel-Guide-VacationRentals)[Flights to Chequamegon Bay](https://expedia.ca/Cheap-Flights-To-Chequamegon-Bay.d6141305.Travel-Guide-Flights)[Chequamegon Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Chequamegon-Bay.d6141305.Car-Rental-Guide)[Chequamegon Bay Vacation Packages](https://expedia.ca/Chequamegon-Bay.d6141305.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/d328119a5dddf118f76475d99a2cc4f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Ski Hotels in Chequamegon Bay, 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 Chequamegon Bay Ski Hotels Tonight [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=6141305&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=6141305&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=6141305&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=6141305&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chequamegon Bay 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) ![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) ![Beach views ](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/7b847f7f.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) ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/d2d182ec.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) ![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) ![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) ![Property amenity](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/52adc64e.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) ![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) ![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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/2ca0a607.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) ![Reception](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232876/e33ed132.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) ### 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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71610000/71607600/71607554/f39e25c1.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) ### 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. " [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/52000000/51870000/51868300/51868228/39b0f607.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) ![Exterior](https://images.trvl-media.com/lodging/72000000/71610000/71609100/71609091/d4594d6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71610000/71609100/71609091/5fd6a583.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!" CA $391 CA $501 total includes taxes & fees Oct 14 - Oct 15 [](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=6141305&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true) ## Top Chequamegon Bay 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." 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[Visit Bayfield](https://www.expedia.ca/Bayfield.dx77465) - [Visit La Pointe](https://www.expedia.ca/La-Pointe.dx3000461829) - [Madeline Island Ferry Line](https://www.expedia.ca/Madeline-Island-Ferry-Line-Bayfield.d6180516.Vacation-Attraction) - [Car rentals near Madeline Island Ferry Line](https://www.expedia.ca/Car-Rentals-In-Madeline-Island-Ferry-Line.d6180516.Car-Rental-Guide) - [Enterprise Rental Cars in Ashland](https://www.expedia.ca/Enterprise-Car-Rentals-In-Ashland.d6170-c15.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Bayfield](https://www.expedia.ca/Hertz-Car-Rentals-In-Bayfield.d77465-c40.Car-Rental-Guide-Suppliers) - [Bayfield Vacation Rentals](https://www.expedia.ca/Bayfield-Vacation-Rentals.d77465.Travel-Guide-VacationRentals) - [Bayfield County Vacation Rentals](https://www.expedia.ca/Destinations-In-Bayfield-County.d553248635976430564.Vacation-Rental-Destinations) - [Book Ski Hotels in Chequamegon Bay on Expedia.com](https://www.expedia.com/Chequamegon-Bay-Hotels-Ski-Hotel.0-0-d6141305-tSkiHotel.Travel-Guide-Filter-Hotels)