Ski-in/out vacation rentals in Ashland County

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Popular amenities for Ashland County ski-in/out rentals

Family-friendly, ski-in/out home rentals

Guest favourite
Condo in Bessemer
4.85 out of 5 average rating, 20 reviews

Unit #5 Lumberjack- Trailside Black River Basin

ErinRating, 5 stars1 month ago
This is the BEST place to stay for a group! Nothing beats a ski in / ski out! The place is perfect, includes lots of important kitchen items for cooking, tons of storage for clothes and gear, great parking, and a hot tub and sauna on site! We love it!! Worth every penny!
Superhost
Condo in Bessemer
4.5 out of 5 average rating, 10 reviews

Unit #1 Lumberjack- Trailside Black River Basin

ScottRating, 5 stars12 months ago
Calley is a really great host. This place is clean and comfortable with two full bedrooms and bathrooms. It’s super convenient to Black River. True ski in / ski out. Easy drive to Jackson Creek and other local areas. These are some of the best accommodations in the area with a great host. Highly recommend! We will be back.
Condo in Bessemer Township
4.71 out of 5 average rating, 17 reviews

Ski In/Out BunkHouse at Black River Basin, Unit #4

AudreyRating, 5 stars2 days ago
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.
Condo in Ironwood Township
4.73 out of 5 average rating, 11 reviews

Rustic Luxury in the North Woods I

MelindaRating, 5 stars30 months ago
Really wonderful place. So beautifully curated. Just fun, and welcoming. Eric was great at communicating everything. It worked perfectly for our trip through the UP, close to the beautiful Porcupine Mtns and all things Western U.P.
Condo in Ironwood
4.87 out of 5 average rating, 31 reviews

The NorthWoods Retreat 2

TammyRating, 5 stars17 months ago
The house was exactly as described in a beautiful setting, right on the ski hill. Beautiful property. All amenities included as described except for soap and shampoo for the shower I recommend bringing your own. The host was extremely responsive and great to work with. We will definitely recommend and planning on making this an annual trip. There are a series of hikes and 5 waterfalls just down the road about 15 minutes. We had a great stay
Superhost
Condo in Bessemer
4.71 out of 5 average rating, 17 reviews

Unit #4 Lumberjack- Trailside Black River Basin

HaileyRating, 5 stars13 months ago
This would be the perfect ski getaway. Right off the ski hill with beautiful views and walkable distance from a waterfall. Cute ski decorations throughout the house. Kitchen had new appliances and everything we needed. Smart TVs in the living room and one of the bedrooms. Big dining table for everyone to fit around. It was warm and cozy. We would love to come back again when there is snow for skiing!
Condo in Bessemer
5 out of 5 average rating, 11 reviews

Ski In/Out BunkHouse at Black River Basin, Unit #3

PattiRating, 5 stars1 month ago
We had a great stay at Alexis and Luke’s place! The space was as described being perfectly located on the ski hill and the host was incredibly responsive to our needs. The comfortable bed and well-equipped kitchen made us feel right at home. Highly recommend this listing for a relaxing getaway!
Condo in Ironwood
4.88 out of 5 average rating, 41 reviews

Rustic luxury in the NorthWoods III

MichaelRating, 5 stars5 months ago
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.

Ski-in/out cabin rentals

Cabin in Upson
4.81 out of 5 average rating, 27 reviews

Gorgeous A Frame in Upson, WI - House 2

XeeRating, 5 stars18 months ago
The gorgeous A Frame cabins were so perfect for our end of summer family trip! We rented out both homes (house 1 + 2), we were so glad that there are 2 full bathrooms in each house, comfortable beds and sofas, the kitchen is fully stocked and functional. Such clean and cute cabins, we especially loved the large patio and fire pit. We took a day trip to Bayfield and over to Big Bay State Park where my now Fiancé proposed. It was so beautiful being back at the cabin at night with the patio lights and gorgeous cabins, this will forever be a memorable trip and we’ll definitely be back. Thank you for a wonderful stay!
Cabin in Upson
4.73 out of 5 average rating, 11 reviews

Rendezvous Cabin in the Whitecap Ski Village!

ClaudeRating, 5 stars4 days ago
House was in a beautiful setting, nestled in the trees. Short hike to the ski hill. Host answered any questions quickly.
Guest favourite
Cabin in Ironwood
4.95 out of 5 average rating, 79 reviews

Central Air • Sauna • Fireplace • “The Bear Cabin”

SeanRating, 5 stars4 weeks ago
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
Cabin in Upson
4.72 out of 5 average rating, 18 reviews

Upson Ski-In/Ski-Out, End-Unit Cabin w/ Fireplace!

MariaRating, 5 stars12 months ago
We had a great time! Nice location …walking distance to the hotel pub where you can get a great fish fry/ food. Family friendly. You can also use the hotel pool for a small fee. Great for kids!
Cabin in Upson
4.63 out of 5 average rating, 30 reviews

Gorgeous A Frame in Upson, WI - House 1

KarleeRating, 5 stars19 months ago
Like many of the other reviews the place is definitely not huge, but we managed just fine with 5 adults and 4 kids. The bunk beds in the lower level were perfect for the kids. Not a ton of fridge and freezer space. Close to the lake, but you will need to use a car if you want to bring the kayaks. Close drive to a lot of things to see. We went to Copper Falls, Lake Superior, and Ironwood. The only complaint was the dryer didn’t seem to work the best and took several cycles to fully dry clothes. That is my only complaint though! Definitely recommended.

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