Ski-in/Ski-out vacation rentals in Ashland County

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Top-rated ski-in/ski-out rentals in Ashland County

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Guest favorite

Rental unit in Glidden

4.93 out of 5 average rating, 56 reviews

Harry's Hangar Apartment ** Glidden, WI.

This cozy apt is the lower level of a ranch house, off hwy 13 in Glidden. 4 rooms - a big bedrm w/ king & single beds, kitchenette with a table, refrig, dishwasher, microwave, dishes, coffee supplies and elect. skillet. The big bathrm has a large shower, & the "Garage Bar" (Aviation theme) is "Harry's Hangar." Walk downtown to the Bear Crossing Conven. Store, bakery, bars etc. Great location for snowmobiling, one block from snowmobile trail & 4 wheeling. Near Copper Falls, Apostle Islands

Guest favorite

Chalet in Upson

4.86 out of 5 average rating, 44 reviews

AlpenhausWI Whitecap, Upson WI Waterfalls Hike Ski

Located at Whitecap Mountains Resort, a recreational wonderland! Near Hurley/Ironwood, MI. Easy access to ski hill , lake for fishing, 22 waterfalls within 30 miles. A quiet retreat with lots of windows! New mattresses, linens, updated baths, functional kitchen. Fireplace, outdoor decks, large comfortable space. Duplex with private entry. PLEASE NOTE: Whiteccap Mountains Resort is currently undergoing remodeling and the hotel, pool, hot tub and golf course are not open at this time.

Superhost

Townhouse in Wakefield

4.88 out of 5 average rating, 51 reviews

SnowRiver Resort Condo ski in/out-(Indianhead Mtn)

LOCATION,LOCATION!!! Relax with the whole family at this peaceful place to stay. It is located right in the heart of Snowriver resort former Indianhead Mountain Ski Resort/Bigsnow . One of our favorite places to go both during the WINTER SKI SEASON and off season . A perfect rental for a large family, a couple families, or adult time away without the kids. The property sits right on the top of the mountain, SKI IN/SKI OUT or during off season, go for mountain biking, ATVing, or go hiking .

Superhost

Home in Ironwood

4.82 out of 5 average rating, 11 reviews

Whispering Woods Chalet - Over 60+ acres!

*New upgrades and new pictures coming soon! Pull into the attached and heated 1-car garage, fire up the wood stove and unwind! Enjoy your morning coffee on the deck watching the wildlife wake up. Spend your days exploring the property trails & look for water fowl nesting in the private pond. Jump on your ATVs or snowmobiles & enjoy 100s of acres of county land surrounding the property. Downhill skiing at 3 different resorts is less than 15 minutes away & snowshoe from the front door.

Guest favorite

Home in Bessemer

5 out of 5 average rating, 14 reviews

Mountain Top Chalet ~ Your Adventure Base Camp!

Located right off Big Powderhorn's Lift 1, Mountain Top Chalet has everything you're looking for in a vacation rental! Tucked into the woods and fully remodeled with your comfort in mind, this private, beautiful home has everything you could want and more! There are 3 levels to this home, 2 living spaces each with a wood burning fireplace, 4 comfy bedrooms and a large loft area dedicated to hosting kids. This home is perfect for large group getaways at any time of the year!

Guest favorite

Cabin in Bessemer

4.98 out of 5 average rating, 66 reviews

Cozy chalet near hiking-biking-waterfalls-trails!!

Come enjoy this cozy and clean duplex chalet! New pillows, sheets, and bath towels. This chalet is located steps from the base of Big Powderhorn Mtn resort, so no need to drive. You can snowmobile/ATV right from the chalet to trail #2, which is a few minutes away. The chalet is close to many beautiful waterfalls. The fully stocked kitchen with crock pot so food can cook while you are out having fun. Ninja coffee maker & grounds provided. 50" & 32" smart TV, and WIFi!!

Guest favorite

Cabin in Ironwood

4.95 out of 5 average rating, 76 reviews

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

Beautiful, peaceful and serene cabin on Wolverine Cross Country Ski Trails in Ironwood, MI. Highlights include a fireplace and electric sauna. Unwind and enjoy all our area has to offer, anytime of year! -- FEATURES -- - 2 BR, 1.5 bath, sleeps 7 - Ski in/out on Wolverine Trails - Sauna - Fireplace with wood supplied - Central Air - Dog Friendly - Gas Genesis grill & Solo Stove - Washer/Dryer - Professionally managed by Tracy - 25+ yrs experience - No Cleaning Fee

Guest favorite

Condo in Wakefield

4.97 out of 5 average rating, 177 reviews

Cozy, Clean, & Quiet 2B/2B Condo w/ Hot Tub!

My clean, cozy, and quiet condo is located at Snow River/Indianhead Resort. It's a brief walk to the Sky Bar on site for food, drink, and the best views from the top of the ski hill in the Upper Peninsula. My condo is the perfect place for your romantic getaway, family trip, after hiking/camping refresh, or peace and quiet on the mountaintop. I provide exceptional communication and top notch responsiveness. You won't be disappointed with your stay!

Guest favorite

Rental unit in Ironwood

4.91 out of 5 average rating, 157 reviews

Welch Creek Inn

This beautiful and spacious apartment is within walking distance to Mt Zion, which can be seen while relaxing in the front porch. This centrally located space is perfect for exploring all the Gogebic range has to offer. Riding trails are right around the corner. This space can accommodate up to 9 people. First bedroom has queen bed, second bedroom has bunk beds, living room has hideabed couch, and front heated porch has a couch and trundle bed.

Guest favorite

Home in Montreal

4.9 out of 5 average rating, 153 reviews

Hilltop Acres - Hike-Bike-Ski-Sled-ATV-Hunt-Fish

Hilltop Acres located in Historic Montreal, WI, just 3 miles from Hurley, WI, is in a quiet location on Trimble Hill. The backyard is adjacent to acres of woods containing the Historic Montreal Ski Trails in winter. For snowmobile & ATV enthusiasts, trails are accessible from the house. Plenty of parking for trailers. Hunting, fishing, alpine skiing & golf nearby as well as the Gile Flowage, many water falls, rivers & lakes to explore!

Guest favorite

Home in Ironwood

4.95 out of 5 average rating, 98 reviews

The Saari House on the ABR Ski Trails

The Saari House is a fully updated farmhouse located on the ABR ski trails. Ski on the freshly groomed trails right out the front door. (Trail passes required.) It's a perfect location for families skiing in and out on a winter getaway or as home base for local waterfall hiking or biking. Guests will have full kitchen, bathroom with tub/shower, washer/dryer, TV with collection of DVDs, various video games and board games.

Guest favorite

Cottage in Upson

4.95 out of 5 average rating, 60 reviews

Stunning 3 bed, 2 bath private lake front cottage.

Take it easy at this unique and tranquil getaway. All season property in wooded setting. Ski-in/ski-out access to Whitecap Mountain, snowmobile trails and ice fishing. Cottage is nestled on the hills of whitecap Mountain overlooking Weber Lake where you can kayak, swim or fish. Winter access requires 4 wheel drive. Public use of the indoor pool for a nominal daily fee in the Whitecap hotel is available nearby.