Title: The Best Ashland, WI Chalets from $385 | Expedia.com [Ashland Travel Guide](https://expedia.com/Ashland.dx6170)[Hotels in Ashland](https://expedia.com/Ashland-Hotels.d6170.Travel-Guide-Hotels)[Vacation Rentals in Ashland](https://expedia.com/Ashland-Vacation-Rentals.d6170.Travel-Guide-VacationRentals)[Flights to Ashland](https://expedia.com/Cheap-Flights-To-Ashland.d6170.Travel-Guide-Flights)[Car Rentals in Ashland](https://expedia.com/Car-Rentals-In-Ashland.d6170.Car-Rental-Guide)[Ashland Vacation Packages](https://expedia.com/Ashland.d6170.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6170&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ashland chalets ![Exterior](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/6cbacc50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/85059b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/0d8b867d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/40000000/39180000/39174200/39174175/088b9f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Northwoods Chalet @ Brickyard Creek, Bayfield [](https://www.expedia.com/Bayfield-Hotels-Northwoods-Chalet-Brickyard-Creek.h39174175.Hotel-Information) Bayfield 10/10 Exceptional (77 reviews) "Beautiful place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan S. $351 nightly $396 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Bayfield-Hotels-Northwoods-Chalet-Brickyard-Creek.h39174175.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/5f4f1c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/7727397e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/46d0584d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39180000/39171900/39171859/f00e9bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodland Chalet @ Brickyard Creek, Bayfield [](https://www.expedia.com/Bayfield-Hotels-Woodland-Chalet-Brickyard-Creek.h39171859.Hotel-Information) Bayfield 9.8/10 Exceptional (59 reviews) "Beautiful private peaceful cabin. We thoroughly enjoyed our visit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacie G. $341 nightly $385 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Bayfield-Hotels-Woodland-Chalet-Brickyard-Creek.h39171859.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/15d9d869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/bd3af196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/bb6d11bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108780000/108775300/108775240/247b5450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2 [](https://www.expedia.com/Upson-Hotels-Spacious-9-Bedroom-Chalet-With-WiFi-And-AC-In-Delightful-Upson-Floor-2.h108775240.Hotel-Information) Upson 10/10 Exceptional (1 review) "A large group of us rented the Davos Chalet for a long weekend. There was more than enough room for us all. The common area was great for us to eat meals and hang out. The kids loved the game room in the basement. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy H. $1,639 nightly $1,729 total Feb 7 - Feb 8 Total with taxes and fees [](https://www.expedia.com/Upson-Hotels-Spacious-9-Bedroom-Chalet-With-WiFi-And-AC-In-Delightful-Upson-Floor-2.h108775240.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.com/Hotel-Search?startDate=2026-02-20&endDate=2026-02-21®ionId=6170&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO) Cottages [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE) Apartments [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Ashland%2C+Wisconsin%2C+United+States+of+America®ionId=6170&latLong=46.592442%2C-90.883794&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FAshland-Chalets.d6170-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FAshland-Chalets.d6170-aaChalets.Travel-Guide-Accommodation) ## Top Ashland Hotel Reviews ![Cedars Motel](https://images.trvl-media.com/lodging/18000000/17280000/17270400/17270312/b658fa50_y.jpg) ### Cedars Motel 10/10 Excellent "The staff and the cleanliness of the room was impeccable!!😀" [](https://expedia.com/Ironwood-Hotels-Cedars-Motel.h17270312.Hotel-Information) ![Bayfield- Charming Condo, Jumping Off Point to Apostles](https://images.trvl-media.com/lodging/19000000/18960000/18956400/18956309/7279b27e_y.jpg) ### Bayfield- Charming Condo, Jumping Off Point to Apostles 10/10 Excellent "The Condo was exactly what we needed. A nice clean place to land and rest our heads and feet after exploring the area. Everything was seemless with booking and the stay." [](https://expedia.com/Bayfield-Hotels-Bayfield-No-Cleaning-Fees.h18956309.Hotel-Information) ![Super 8 by Wyndham Ashland](https://images.trvl-media.com/lodging/1000000/460000/459600/459528/23163c47_y.jpg) ### Super 8 by Wyndham Ashland 10/10 Excellent "The room was clean, fresh smelling and flawless. Staff was friendly and welcoming. One of the best Super 8's we have ever stayed at. " [](https://expedia.com/Ashland-Hotels-Super-8-By-Wyndham-Ashland.h459528.Hotel-Information) ![AmericInn by Wyndham Ashland](https://images.trvl-media.com/lodging/1000000/610000/601700/601615/8344a88e_y.jpg) ### AmericInn by Wyndham Ashland 10/10 Excellent "Clean room. Spacious. Easy check in." [](https://expedia.com/Ashland-Hotels-AmericInn-By-Wyndham-Ashland.h601615.Hotel-Information) ![The Washburn Inn - On the Lake](https://images.trvl-media.com/lodging/1000000/460000/459700/459665/b643ecc7_y.jpg) ### The Washburn Inn - On the Lake 10/10 Excellent "Great staff, great room! Loved being right on the bay!" [](https://expedia.com/Washburn-Hotels-The-Washburn-Inn-On-The-Lake.h459665.Hotel-Information) ![Legendary Waters Resort & Casino](https://images.trvl-media.com/lodging/62000000/61480000/61478500/61478483/00893773_y.jpg) ### Legendary Waters Resort & Casino 10/10 Excellent "Staff was helpful!" [](https://expedia.com/Bayfield-Hotels-Legendary-Waters-Resort-Casino.h61478483.Hotel-Information) ![Whitecap Mountains Resort](https://images.trvl-media.com/lodging/104000000/103490000/103488600/103488532/76fce137_y.jpg) ### Whitecap Mountains Resort 10/10 Excellent "We had a great stay at Whitecap. The 3 Queen Suite was perfect for our group, plus our dog Murphy. It was very clean and ready upon our arrival. They did their best to keep lifts open and skiing available despite the very very cold temps. The staff was friendly and Denali was a highlighted staff member throughout the weekend that we saw! Kudos to her hard work. We hope to do another weekend stay in the future here. " [](https://expedia.com/Upson-Hotels-Whitecap-Mountains-Resort.h103488532.Hotel-Information) ![Blue Wave Inn](https://images.trvl-media.com/lodging/27000000/26690000/26680700/26680614/198db952_y.jpg) ### Blue Wave Inn 10/10 Excellent "Clean, generous amenities, spacious, very comfortable" [](https://expedia.com/Ashland-Hotels-Blue-Wave-Inn.h26680614.Hotel-Information) ![Quality Inn Ashland - Lake Superior](https://images.trvl-media.com/lodging/1000000/30000/21800/21748/979c6191_y.jpg) ### Quality Inn Ashland - Lake Superior 10/10 Excellent "This hotel feels like staying in a cabin on the lake. The room was beautifully themed but also very clean. The view out the window of the lake was spectacular. The breakfast was actually quite tasty. Loads of options and even a fun pancake machine. The staff were extremely friendly and made you feel at home. They had great dinner suggestions too." [](https://expedia.com/Ashland-Hotels-Quality-Inn-Ashland-Lake-Superior.h21748.Hotel-Information) ## Find out more about Ashland ## Ashland Chalets information | Number of reviews | 136 | | ----------------- | ---------- | | Accommodation | 15 Chalets | | Lowest Price | $385 | | Highest Price | $1,729 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Ashland Historical Museum ](https://www.expedia.com/Ashland-Historical-Museum-Hotels.0-l6323159-0.Travel-Guide-Filter-Hotels) - [Hotels near Chequamegon Bay Golf Course ](https://www.expedia.com/Chequamegon-Bay-Golf-Course-Hotels.0-l6323167-0.Travel-Guide-Filter-Hotels) - [Hotels near John F. 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