Vacation rentals in Upson

The Snuggery @ Whitecap ~ Ensuite Sauna *Now with

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, air conditioning, 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 Whitec

Red Ridge: updated 1BR Getaway by Trails-Ironwood

Nestled in a peaceful neighborhood, Red Ridge Retreat is a cozy, renovated 1 bed/1 bath home. Located just a 5-minute drive from downtown Ironwood and ABR X-country ski trails, this retreat offers easy access to ski resorts, hiking trails, waterfalls, and Lake Superior coastline within a 30-minute drive! With ample parking for vehicles and outdoor gear, enjoy year-round outdoor recreation right at your doorstep. Book your stay now for a serene getaway full of relaxation and adventure in nature!

Cedar Hill Retreat, King Bed, 108 Acres of Privacy

Winding up the driveway you are greeted by a home located on 108 acres of privacy, yet only 8 miles from town! This place is a clean (enhanced cleaning routine), fresh, and relaxing with breathtaking views! With enough space for a whole group or private couple getaway, this home offers the perfect opportunity to make memories lasting a lifetime. Gather around the wood stove after a long winter day full of activities available close by, or relax on the back deck watching the sun set in summer!

"Bakery Bungalow" -Sweet Accommodations & Nature !

Our Bakery Bungalow (owned by a baker) is a peaceful retreat in a semi rural, prime location near snow trail system, 2 miles from historic downtown shops, hiking / biking trails, on the outskirt of town (Ironwood Township) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior beaches, large private wooded yard with fire pit, private parking, 1 stall garage if needed in winter. P.S. Bakery Treats provided !!!

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

National Forest Lakeside Retreat

Escape to this beautiful cabin nestled in the woods on a serene lake. With its cozy layout and large windows, you'll feel right at home surrounded by nature's beauty. Enjoy breathtaking views of the dark sky at night and wake up to the peaceful sounds of the National Forest. Explore endless adventures with hiking, ATV, and snowmobile trails just steps away. Unwind on the deck and take in the tranquility of this hidden gem. Book your getaway now and experience the ultimate retreat.

Pabst Street Retreat - Cozy 5 bedroom 7 bed home

The house is located right in Ironwood. We are 3 miles from ABR Trails, 4 miles from Wolverine Ski Trails, 1 block from the snowmobile and bike trails, 1 mile from Miners Heritage Park, 18 miles from Black River Harbor, 10-15 miles from many downhill ski slopes and half a mile from downtown Ironwood. A foosball table is in the basement for some extra family fun. There also are games, books and puzzles in the living room. Final price includes the 15.5% Airbnb fees.

Hill Street Retreat • Boho Stay w/ Infrared Sauna

Welcome to The Hill Street Retreat! This cozy 2-bedroom, 1-bath boho home is designed for comfort and relaxation. Enjoy a fully equipped kitchen, coffee bar, dining room, laundry, Roku TV, games, and two dedicated workspaces. Unwind in the private basement wellness room featuring an infrared sauna, yoga space, and light workout equipment. Conveniently located near downtown Ironwood and just minutes from skiing, hiking, waterfalls, and Lake Superior adventures.

Charming Lakefront Cabin

Your perfect Northwoods escape! This cozy 2BR cabin mixes rustic charm with modern comfort with an unbeatable lake view. Set within the Sconnie Seasons property and just minutes from ATV/snowmobile trails, the cabin shares scenic lakeside grounds with other private cabin rentals and Lucky’s - a historic on-site bar. Plenty of parking for vehicles/trailers plus a boat launch and dock access. Kayaks, life jackets, and firewood included for all guests.

Copper Falls Cabin

Copper Falls Cabin sits on 80 acres directly adjacent to Copper Falls State Park near Mellen, WI. The renovated rural farmhouse features 4 bedrooms and 1.5 baths. Copper Falls State Park is right out your door, and places like Bayfield and the Apostle Islands National lakeshore are within an hour’s drive. This is your perfect basecamp to explore the South Shore of Lake Superior in both Wisconsin and the western Upper Peninsula of Michigan.

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!

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.