Family-friendly holiday rentals in Ashland County

I've stayed at Calley's places many times. You can beat the ski-in/ski-out location. She has made some nice upgrades to the units over the years and always does a great job with the communication. Her property manager is a great guy and is very responsive if issues arise. You can't go wrong staying here.

Great place to stay at. Nothing beats being able to just walk out of you back door and be on the ski hill. Has everything anyone would need plus more.

Comfortable, clean second floor condo a short drive from Bayfield with wooded view from kitchen window. Working jacuzzi and adequate cooking supplies. Jon was quick to respond to questions.

A great location. In walking distance to a ski lift. The place was clean and it was awesome being able to have a fire in the fire place. Peter checked in with us in person to see if we needed anything. Also, he was very responsive to a couple questions I had prior to arriving. We will be back.

This is a perfect place if you are skiing at the Snowriver Mountain hills. The place is a little dated and the walls are a little thin, but we didn't want to spend our days in the condo so it didn't bother us. Peter is very polite and responsive.

This is a very nice and spacious place in a convenient building whether you are skiing at Black River (which is ski in - ski out) or Jackson Creek Summit which is only 10 minutes away and has easy parking. Calley is super responsive and easy to work with.

We came to the Upper Peninsula for fall colors. The location (at the base of a ski hill) was right on the route for one of the best color drives in the area and close to the Copper Peak ski jump that offers rides to the top to see the surrounding countryside. The charging station for our Tesla was super close at the main lodge. Eric's place was super clean, quiet and comfortable. We liked having the pinball machine for some extra fun.

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

enjoyed the accommodations and tha golf course.

Sweet little cabin on a lake with woods all around. Well maintained, clean, and a full kitchen. It was a perfect place to unwind and be at peace with our family.

Jon's place was great for me and my wife with our 2 small dogs. we were the first renters of the season and there wasn't any coffee, so Jon immediately gave me a $15 refund. great directions for hiking trails, nice quiet place and great location for visiting the Apostle islands. we would definitely stay there again.

Our little family of 4 loved staying in the cottage nestled in the woods. My husband and I slept in the sunroom surrounded by the forest with the windows open listening to the wind in the trees or the rain on the leaves. SO peaceful and close to town. There is no yard or fire pit but the island was our playground.

Located on the Wolverine ski trails was awesome. Winter wonderland in a fantastic setting and was truly magical during snow storms. Our two dogs were equally impressed

We absolutely loved staying at Jason Black River Retreat! It had everything we needed, was very clean, the property and trails well maintained. We will be back!

Tim and Roxanne were the nicest hosts we’ve ever dealt with and their place is truly spectacular. It was a privilege to stay there. It is beautiful, peaceful and such an idyllic setting! They also keep their place in tip top shape and have everything you could ever need available for you. Hammocks, boats, bikes… whatever you need. We’ve stayed at a ton of rentals up north as well as internationally, and none come close to staying with Tim and Roxanne at their place. Plus, the lake is pristine and private to the twenty some property owners that have a home on it. Great fishing, clear water and even some sandy spots. Oh, and Al Capone’s brother owned a house on this lake, so there’s a lot of cool history too. So glad we found this place…. Thanks Tim and Roxanne!

Very cozy house in a beautiful setting. Location is great halfway between Bayfield and Cornucopia

Location was incredible and the host was very responsive. Would totally stay there again!

This place was as described and had plenty of amenities and essentials. It had a stocked kitchen for cooking on-site and it was a comfortable place for our group. Located in a friendly area and close to everything that Iron County, WI has to offer. I would recommend for a northern getaway.

This place is rustic and quite comfortable. We especially enjoyed the additional storage space to keep all of our ski gear organized. There is an additional sink in the one bedroom, which was handy. We didn’t use the fireplace or sauna, but cooked in a couple nights and had everything we needed to do so.

Very peaceful, cozy and clean. Exceptional location

The house was very cute and clean, well-stocked, especially kitchen and bath amenities. Instructions, directions, and check in/check out very straight forward which is appreciated. Location was great as it was a couple miles from a grocery store and the golf course. Sauna was a huge bonus. It was nice to have such a cozy home to stay while we spent a couple days in Ironwood.

We really enjoyed our stay. The condo was just as she described it and it was a homey stay for us while we enjoyed a weekend of skiing. We really liked having a fire in the evenings and there was space for us to dry our clothes from the day. The only bummer was having people stay above us. The floors were very creeky, but ear plugs helped with that while sleeping. Overall, we were happy with our choice to stay here and would definitely do it again.

Guys ski trip to ABR and Big Powderhorn. We had plenty of space for our group and enjoyed the gathering space playing games at the large dining room table. Extremely quiet at night, we were pleasantly surprised how close it was to everything including skiing and restaurants. I highly recommend.

Becky was very responsive, and helpful to us all! We stayed here with 17 people and everyone had what they needed! And the gameroom is key! People can stay up and talk and play games while others are able to sleep quietly. It's great