Chalet holiday rentals in Ashland County

4.75 out of 5 average rating, 4 reviews

The Snuggery @ Whitecap Ski Resort

Get ready for amazing views and cozy nights by the wood burning fireplace at the newly updated Snuggery! Located in the Whitecap Ski Village, this 3+ bedroom, 2 baths home is the perfect year round base camp for all of your outdoor adventures! Complete with an ensuite electric sauna, large wood burning fireplace, fully stocked kitchen, coffee bar and 2 large exterior decks, the Snuggery has everything you need to make your time away extra special! Aside from the amazing Whitecap Resort and Wine

4.95 out of 5 average rating, 66 reviews

Chalet in Ironwood

Stunning Log Cabin Getaway at The Hannu Haus

The stunning Hannu Haus is a Scandinavian built log home, built log by log with timber harvested from the property right in Ironwood, MI. Custom kitchen with hand laid concrete countertops & built in trivets. Open shelving for your groceries at ease. No need to leave the lodge if you don't want to, the kitchen is fully equipped with all the extras you didn't even know you needed. Jura super automatic espresso machine to have your fancy drinks without having to leave the comforts of the lodge.

4.94 out of 5 average rating, 124 reviews

Cabin Fevers 2 @ Big Powderhorn & Pet Friendly!

Cabin Fevers is your cozy UP getaway with lots of beautiful and awesome things to see nearby every day. We are located at the foot of Powderhorn Mountain. Snowriver Mountain Resort (previously Indianhead) is also nearby. We are close to Wolverine X-Country & Snowshoe Trails. ABR, Miner’s Memorial Heritage Park & Montreal trails are also a short drive away. We are close to Copper Peak, Black River Harbor, Little Girls Point, & many waterfalls. Porcupine Mountain State Park is an hour away.

4.96 out of 5 average rating, 113 reviews

Big Chalet with Hot Tub on Big Powderhorn Mountain

This is it! Our place is a great place for your big family or group to ski, snowmobile or just relax. We offer plenty of room with 5 private bedrooms. We have an area of open space including a living room and kitchen that is MASSIVE. It has 2 fireplaces. A gas fireplace in the living room and if you prefer wood there is a wood one in the kitchen. Time to clean up, we have 3 full bathrooms stocked with shampoo, conditioner, soap. Then a sauna and hot tub to relax. Also a rec room Wi Fi

4.83 out of 5 average rating, 12 reviews

Oui Ski Inn: Powdery Peak

Escape to the Upper Peninsula and enjoy this cozy 2-bedroom, 2-bath duplex in Bessemer, MI., with shared amenities to help you unwind after a day of adventures. Perfectly located just a short walk from Big Powderhorn Mountain, this retreat offers easy winter access to skiing, snowboarding, and more. Explore nearby trails, waterfalls like Bond Falls, and enjoy fishing, kayaking, and biking. In autumn, savor vibrant foliage and local berry-picking—making this a perfect year-round getaway.

4.95 out of 5 average rating, 157 reviews

Chalet in Ironwood

Swiss Chalet by waterfalls and Lake Superior

You will love our Swiss-inspired Chalet in the Alpine Village at the Big Powderhorn Mountain Resort. The 1500 sq feet Chalet is surrounded by 0.6 acres of woods for your privacy and enjoyment of this gorgeous area. You are 5 minutes away from the ski slopes at Big Powderhorn, 15 minutes from Indianhead and Blackjack resorts, Copper Peak, numerous gorgeous waterfalls on Black River and 19 min away from the Black Harbor Pavillion and Lake Superior. This is your all season destination!

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Chalet in Ironwood Township

4.96 out of 5 average rating, 113 reviews

Modern Chalet -AC, hot tub, sauna + pets welcome

No hidden cleaning fees! A recently updated chalet in the village at Big Powderhorn Mountain. Timbuktu is located at the end of a private cul-de-sac and within a short 10-minute walk to Big Powderhorn Lodge and ski lifts. Uniquely, Timbuktu is also a small farm and is powered by an on-site solar system which is supplemented by other renewables. Timbuktu is a duplex with the owners living next door. Who are happy to assist with questions and advice. Pets welcome at $20/pet/night.

Chalet in Ironwood Township

4.87 out of 5 average rating, 15 reviews

Rocky Pines U.P ~ Ski Area, Sauna, & Pets Allowed

Have fun with the whole family at this cozy remodeled A-frame Chalet near Big Powderhorn Ski Resort in Powderhorn Village. Close to all the action for Biking, Hiking, Waterfalls, Fishing, Off-Road adventures, X-country Skiing, Snowboarding, Snowshoeing, Skiing, and Snowmobiling. Chalet has 4 bedrooms - Perfect for families with children ~ 2 Queens ~ 4 Twins ~ 2 Full Bathrooms: (1 each floor) ~ Classic cedar lined Sauna on upper floor ~ Free WiFi, Cable, Telephone

Top guest favourite

Chalet in Bayfield

4.98 out of 5 average rating, 158 reviews

The Acorn of Little Sand Bay Dog Friendly

Modern, rustic, Aframe cabin in the woods with beautiful, simple décor, fully equipped kitchen, new appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, heated tile floor, walk-in shower, shampoo/conditioner/bodywash provided. King-size bed in the loft area. Smart TV, wifi. Books, games, bluetooth speaker The woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

4.95 out of 5 average rating, 249 reviews

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

My place is located at Big Powderhorn Ski Resort and close to Lake Superior, family-friendly activities, great views, restaurants and dining. You’ll love my place because of the location, the ambiance, the outdoor space, and the neighborhood. My place is good for couples, solo adventurers, and families (with kids). Dog friendly! Outdoor Hot Tub! Wood burning Fireplace with wood supplied! Great cell service! TV, Cable, Roku, WIFI....great entertainment! Washer/Dryer

4.91 out of 5 average rating, 215 reviews

Hot Tub • Fireplace • Dog Friendly•Big Powderhorn

Located in the Village area of Big Powderhorn Ski Resort, this cozy A-frame offers comfort and convenience. Features include a covered HOT TUB to soothe your muscles at the end of a day of hiking, skiing or sledding. Close to Copper Peak, Lake Superior, waterfalls, bike trails and more. Inside you will find a wood FIREPLACE, 2 loft bedrooms with 4 beds, 1 full bath, fully equipped kitchen, Cable TV and WIFI. No cleaning fee!!!

4.94 out of 5 average rating, 34 reviews

Crossbow Chalet is in the heart of the Northwoods

Crossbow Chalet is the place to be this winter. Walking distance to Big Powderhorn Mountain and offering a free ski locker at the lodge, 10 minute ride to Big Snow Country, Blackjack Resort and Indianhead Mountain. Guests are saying the skiing is great. Chalet will be waiting after a day of skiing with a large outside deck with a hot tub and a cozy fireplace. Give us a try. We know you will enjoy your stay!

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Popular amenities for chalet rentals in Ashland County

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Family-friendly chalet rentals

4.8 out of 5 average rating, 92 reviews

Chalet in Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield

JohnRating, 5 stars11 months ago

Very peaceful, cozy and clean. Exceptional location

4.81 out of 5 average rating, 135 reviews

Indianhead duplex chalet with a hot tub 2375

BethanyRating, 5 stars2 months ago

Wedel Haus was a great little triplex unit that is super close to Snow River's Jackson Summit. There are other cabins around, but it is a very quiet neighborhood. The cozy indoor gas fireplace and outdoor hot tub on the deck were perfect for our ski weekend. The hot tub and deck area are shared so there is a fair amount of communal outdoor space. Having friends rent the other units is a nice option. There is plenty of parking and it is easy to find.

4.92 out of 5 average rating, 24 reviews

Clean and Quiet Family Chalet at Jackson Creek

LarissaRating, 5 stars4 months ago

This is our 3rd year here. Great location

4.67 out of 5 average rating, 36 reviews

Indianhead Chalet Lower Unit

ChristyRating, 5 stars2 months ago

Tim’s place was very relaxing for the early weekend getaway! Would def stay with host again!

4.85 out of 5 average rating, 118 reviews

Indianhead Red Lodge by Ski Resort

JenniferRating, 5 stars3 months ago

We had an amazing stay. The ski hill is right up the road. It was within minutes of the nearest towns. And lots of space for everyone to spread out. We will definitely book this again!

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Lakefront chalet rentals

KokkieRating, 5 stars4 months ago

Ski Chalet of Whitecap Mountain

Keri’s condo is a perfect place as a family to enjoy all amenities that Whitecap Mountain has to offer. The view over the ski slope and the fire place are awesome. The condo is spacious and is ideal for a family get together and is very well furnished. It has everything you might need.

4.33 out of 5 average rating, 3 reviews

Sarajevo House at Ski Resort

LibbiRating, 5 stars5 months ago

We enjoyed our stay! The location is great! It's a quick walk over to the main lodge and main ski lift. It's also got a great view of the lake. The host was very helpful and responsive and answered all questions right away. The chalet was very clean too. There have been updates to the space, like new floors and a large TV. The furniture and appliances are dated but functional. There was plenty of space for our family of four. If we come back up to Whitecap, we'd definitely stay here again!

4.94 out of 5 average rating, 16 reviews

Mineshaft Chalets 1 at Whitecap Mountain Resort

JustinRating, 5 stars22 months ago

Beautiful location! Lake access was great for kayaking and fishing for trout, rock bass, bluegills and sunfish. Also only 30 minutes from Lake Superior where we were able to see the Northern Lights and search for Yooper Lights. Lots of lawn space for the kids to play baseball, football and soccer. Having two kitchens was AMAZING when cooking for a large group. And multiple bathrooms were also very helpful... never had to wait! Kelvin was very responsive to answering any questions. The only downside was limited parking right at the Chalet... but lots of nearby parking is available, so no biggie. Overall an amazing stay!!!

4.89 out of 5 average rating, 35 reviews

Mineshaft Chalets 2 at Whitecap Mountain Resort

CindyRating, 5 stars10 months ago

We had plenty of room for our entire family. The lake and surrounding area is beautiful with great proximity to Lake Superior and lots of trails. We would stay here again.

SarahRating, 5 stars5 months ago

Chalet at Ski Paradise

Could be ski in and out with lots of snow on the ground. Right on the Lake. Easy 3 min walk to the Whitecap resort for dinner or hot tub.