
Ski-in/Ski-out holiday 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.

Cute & Cozy 1B/1B Condo w/ Jetted Tub!
My clean, cozy, quiet, and Completely remodeled condo is located at Indianhead/Snowriver Resort. It's a brief walk to the Sky Bar/Jack's Cafe 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, ski vacation, or peace and quiet on the mountaintop. I provide exceptional communication and top notch responsiveness. You won't be disappointed with your stay!
4.96 out of 5 average rating, 115 reviews
TrailView2HotTub/ColdPlunge/Theater/Massage/MtView
This luxury condo has it all. You can't beat the location & all amenities at this price. Next to Powderhorn's parking lot & Ottawa National Forest. 1700 sq ft condo in wooded area. Breathtaking views. All private. Indoor 24/7 8-person hot tub, cold punge, sauna, zero-gravity massage chair, central air, 5 HEPA air purifiers, infinite hot water, 4k 65" tv, high-end Atmos theater, memory foam beds, RO water filter, 1GB WIFI 7, fireplace, smart grill, & stocked kitchen. 3 bedrooms and 2 full baths.
4.86 out of 5 average rating, 131 reviews
UTV/ATV Lodge w/Games + Firepit: Schnickelfritz #4
Schnickelfritz #4 is a fun, one-of-a-kind lodge retreat steps away from Big Powderhorn Mountain, putting year-round adventure right at your doorstep! With easy access to the main chalet, ski-lifts, and nearby trail systems, enjoy skiing in winter and convenient access to hiking, biking trails, and ATV riding in the warmer months. After a day of action, kick back in the shared basement lounge with a Sauna, Pinball, Foosball, Pool Table, and more! Free washer and dryer included. Pets $50 per stay
4.97 out of 5 average rating, 32 reviews
Liftside Loft - SI/SO Condo @ Jackson Creek!
Relax by the fireplace or the ensuite sauna in this large family-friendly, SI/SO condo, located on the new Jackson Creek Ski Hill! This 4 bedroom + loft condo has plenty of space to spread out and enjoy your time away. Special features like the cedar-lined sauna, gas fireplace, and private deck with propane grill make this rental a perfect year round getaway! Guests are also within walking distance to the ski lodge restaurants for great food and drinks, ski rentals, and purchasing lift tickets.
4.89 out of 5 average rating, 36 reviews
Powderhorn Condo Snowdrift #5
Keep it simple at this peaceful condo conveniently located near Powderhorn ski hill and snowmobile/UTV trails. New air conditioner, ceiling fan and living room Smart TV. Bedroom also has a Smart TV. There is a bonus room, with patio doors, which has a 72” futon. This could be opened for added sleeping. The room also works great for an away from home office. The patio is available but is a work in progress. Unfortunately, we are not able to offer power for vehicles and hybrids at this time.
4.88 out of 5 average rating, 16 reviews
Ski In & Ski Out
Hike, bike, ski, snowshoe, sightsee…we can go on! This stunning ski-in/ski-out condo offers unparalleled access to Jackson Creek Summit part of the Snowriver Mountain Resort. Situated on the top of the hill, this peaceful residence ensures you can hit the slopes as soon as you step out the back patio door. The perfect retreat for access to many area destinations including Porcupine Mtns, waterfalls, ski hills (Jackson Creek, Black River Basin, Big Powderhorn, Whitecap) and much more!
4.95 out of 5 average rating, 62 reviews
Oui Ski Inn: Snowy Summit
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.
5.0 out of 5 average rating, 3 reviews
HoLmestead at ABR XC Ski In/Out Dog-Friendly
XC Ski In/Out (& Snowshoe) directly from your door to ABR Trails. Newly offered 2BR/1BA (4 beds/sleeps 6) Dog-friendly Farmhouse. Located right on ABR XC Ski Trails (via Deer Trail/Jack Flats- suitable for all skier levels, skate or classic). Very convenient location for multiple skier abilities, family & dog-friendly, ALL ABR Trailside!! This is THE closest (non-ABR owned) lodging available to the trailhead. Plenty of off-street parking for large trailers.
4.86 out of 5 average rating, 37 reviews
2BR Condo | Outdoor Firepit | Near UP Waterfalls
Black River Road is one of the best drives in the Upper Peninsula in any season — and in summer, it's something else. Five named waterfalls, towering hemlocks, and a dramatic finish at Black River Harbor on Lake Superior. Alpen Villa's-Après 2 is your starting point. Back at the condo, you've got 1,000 square feet of genuine comfort for eight: two bedrooms, two full baths, a fully equipped kitchen, and a wood-burning fireplace with firewood included.
5.0 out of 5 average rating, 14 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!
4.92 out of 5 average rating, 194 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.
4.95 out of 5 average rating, 132 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.
4.96 out of 5 average rating, 84 reviewsPopular amenities for Ashland County ski-in/ski-out rentals
Ski-in/ski-out house rentals

Chateau Relaxo~Jackson Creek Ski
5.0 out of 5 average rating, 13 reviews
Mountain Top Chalet ~ A/C & Close to Rec Trails!
5.0 out of 5 average rating, 41 reviews
Million Dollar View! Whitecap Mtns Ski Resort Home
5.0 out of 5 average rating, 3 reviews
Lakefront 5 Bedroom 3 bath Northwood Chateau 2 & 4
5.0 out of 5 average rating, 5 reviews
Diggins Trailside Cottage
4.89 out of 5 average rating, 9 reviews
Comfy Bear Ski in/Out Condo
5.0 out of 5 average rating, 13 reviews
House on the Highlands
New place to stay
Cozy 2BR Chalet w/ Sauna & Fireplace
4.86 out of 5 average rating, 36 reviewsFamily-friendly, ski-in/ski-out home rentals

Piper Haus Unit 1 Chalet 18 guests
4.93 out of 5 average rating, 42 reviews
Ski Chalet of Whitecap Mountain
5.0 out of 5 average rating, 6 reviews
Lodge Stay w/ Games + Firepit: Schnickelfritz #1
5.0 out of 5 average rating, 9 reviews
Harry's Hangar Apartment ** Glidden, WI.
4.92 out of 5 average rating, 79 reviews
Ski Inn
5.0 out of 5 average rating, 9 reviews
Mineshaft Chalets 2 at Whitecap Mountain Resort
4.9 out of 5 average rating, 39 reviews
Ski in/out Condo @ Snowriver Jackson Creek For 6
4.83 out of 5 average rating, 12 reviews
The Great Escape!
4.69 out of 5 average rating, 35 reviewsSki-in/ski-out cabin rentals

The Loft - Ski in/ski out/ Snowmobile Access
4.67 out of 5 average rating, 3 reviews
Slopeside 1B/1B Retreat-Fireplace & Massage Chair
5.0 out of 5 average rating, 3 reviews
4BR/3BA Chalet-WiFi-AC, ATV, Hike, Ski-InOut, Hunt
4.92 out of 5 average rating, 13 reviews
Adventure Basecamp A-Frame - House 2
4.83 out of 5 average rating, 30 reviews
Valkommen Haus, Ski In Ski Out at Whitecap Mt.
New place to stay
Penokee A-Frame near Whitecap Slopes! House 1
4.65 out of 5 average rating, 31 reviews
Cabin 5 | Cozy Trailside Glamping, All Seasons
4.67 out of 5 average rating, 3 reviews
Glamping in Cabin 1 Cozy Ski/Snowmobile Access
4.5 out of 5 average rating, 4 reviewsDestinations to explore
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