Title: Book the Best Madeline Island Ski Hotels in 2026 from CA $156 | 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)

![Big Bay State Park, Madeline Island](https://images.trvl-media.com/place/635019186360348672/03efc056-b655-418f-ba97-fb2072770447.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Kate Johnson

# Find Ski Hotels in Madeline Island, WI from CA $156

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## Check availability on Madeline Island Ski Hotels

Tonight

[Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635083902716&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Madeline Island ski hotels

![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)

![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)

### Legendary Waters Resort & Casino

[](https://www.expedia.ca/Bayfield-Hotels-Legendary-Waters-Resort-Casino.h61478483.Hotel-Information)

Bayfield

8.0/10

Very good

(406)

"Front desk daytime lady was excellent."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paul

[](https://www.expedia.ca/Bayfield-Hotels-Legendary-Waters-Resort-Casino.h61478483.Hotel-Information)

![Boating](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/b643ecc7.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)

![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

[](https://www.expedia.ca/Washburn-Hotels-The-Washburn-Inn-On-The-Lake.h459665.Hotel-Information)

Washburn

8.6/10

Excellent

(1000)

"Very nice accomodations and very friendly staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jayne

CA $150

CA $168 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Washburn-Hotels-The-Washburn-Inn-On-The-Lake.h459665.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)

![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)

![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

[](https://www.expedia.ca/Ashland-Hotels-AmericInn-By-Wyndham-Ashland.h601615.Hotel-Information)

Ashland

7.8/10

Good

(1000)

"Very welcoming, breakfast was good, pool area was clean and well kept. We’ll be staying again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sheila

CA $139

CA $156 total

includes taxes & fees

Dec 23 - Dec 24

[](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)

![Restaurant](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/5acfd4b9.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)

![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

[](https://www.expedia.ca/Ashland-Hotels-Blue-Wave-Inn.h26680614.Hotel-Information)

Ashland

9.8/10

Exceptional

(582)

"Very nice rooms with a beautiful view "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gerald

[](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)

![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)

![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

[](https://www.expedia.ca/Ashland-Hotels-Best-Western-The-Hotel-Chequamegon.h5232876.Hotel-Information)

Ashland

8.6/10

Excellent

(1002)

"Clean rooms. Good variety of breakfast options."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gina

CA $144

CA $162 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Ashland-Hotels-Best-Western-The-Hotel-Chequamegon.h5232876.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)

![Indoor pool, open 6:00 AM to midnight, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/28502afa.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

[](https://www.expedia.ca/Ashland-Hotels-Super-8-By-Wyndham-Ashland.h459528.Hotel-Information)

Ashland

8.0/10

Very good

(1001)

"We would definetly stay here again. Very friendly staff."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

michael

CA $150

CA $168 total

includes taxes & fees

Dec 23 - Dec 24

[](https://www.expedia.ca/Ashland-Hotels-Super-8-By-Wyndham-Ashland.h459528.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)

![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)

![Front of property](https://images.trvl-media.com/lodging/97000000/96480000/96477800/96477730/25a37d05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### St. James Social

[](https://www.expedia.ca/Bayfield-Hotels-200-Rittenhouse-Ave.h96477730.Hotel-Information)

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

[](https://www.expedia.ca/Bayfield-Hotels-200-Rittenhouse-Ave.h96477730.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/f00e9bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/fd9d80bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/329b92a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/941e4c3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Woodland Chalet @ Brickyard Creek, Bayfield

[](https://www.expedia.ca/Bayfield-Hotels-Woodland-Chalet-Brickyard-Creek.h39171859.Hotel-Information)

Bayfield

9.8/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Wendy L.

CA $273

CA $530 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Bayfield-Hotels-Woodland-Chalet-Brickyard-Creek.h39171859.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/54000000/53630000/53620200/53620159/c77c119c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Bayfield-Hotels-Apostle-Iss-Gatewaynext-Scenic-Marinasfireplacejacuzzicorner-W-4-Windows.h53620159.Hotel-Information)

Bayfield

9.8/10

Exceptional

(229)

"Location was perfect!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

amy g.

CA $95

CA $207 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Bayfield-Hotels-Apostle-Iss-Gatewaynext-Scenic-Marinasfireplacejacuzzicorner-W-4-Windows.h53620159.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)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71610000/71607600/71607554/89acf76c.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)

### Bayfield Fruit Loop Retreat - Main Cottage

[](https://www.expedia.ca/Bayfield-Hotels-Bayfield-Fruit-Loop-Retreat-Main-Cottage.h71607554.Hotel-Information)

Bayfield

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matthew

CA $377

CA $470 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Bayfield-Hotels-Bayfield-Fruit-Loop-Retreat-Main-Cottage.h71607554.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=2025-12-27&endDate=2025-12-28&regionId=553248635083902716&adults=2&location_highlights_explore=ski&sort=RECOMMENDED&openPlayBack=true)

## Top Madeline Island Hotel Reviews

![Best Western The Hotel Chequamegon](https://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)

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