Vacation rentals in Upson

Bakery Bunkhouse - Sweet Amenities & Nature !

Yooper Delights Baking Co. is now a family style home with beds for 5. A large fully stocked kitchen (including bakery treats) Scandinavian cottage with a sleeping loft (queen+ single size bed) plus a queen sleeper sofa on main level, large antique dining table, Swedish gas fireplace welcome you ! The patio doors open to private patio, large back yard, picnic flower garden & wildlife viewing ! We are located 2 miles from town, in a semi rural, peaceful township, close to trails & Lake Superior!

Value · Location · TV

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!

Location · Value · Comfort

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.

Location · Value · Kitchen

Green Haven | Cozy Home Near Heart of Downtown Iwd

Welcome to our freshly renovated, boho themed home near the heart of downtown Ironwood, MI. This stylish place to stay is perfect for group trips. We offer everything you need for a comfortable + enjoyable visit. Take a quick 10-15 minute stroll to check out local shops + eats. With your own private home, you can come + go as you please. We also own the house next door, so if you have a big group you can book both (13 guests total)! Here is that listing: airbnb.com/h/parkplaceiwd

Family · Location · Walkability

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.

Value · Family · Hiking

Alpenhaus Lower ~ Whitecap Ski Village!

Welcome to Your Serene Northwoods Getaway at Alpenhaus Chalet! This charming lower unit chalet is the perfect destination for a cozy weekend retreat, providing plenty of space for your group to relax. Tucked away in the Whitecap Mountains Ski Village near Upson, WI, you’ll be situated in the heart of northern Wisconsin's ski region, just a quick half-hour drive from Lake Superior and Michigan's Upper Peninsula. Make lasting memories at Alpenhaus Chalet on your next adventure!

Location · Biking · Comfort

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.

Location · Family · Hospitality

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.

Location · Family · Check-in

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!

Value · Location · Hospitality

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.

Family · Location · Hospitality

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.

Family · Location · Grill

Hiawatha’s Hideaway-cozy 2BR getaway, near trails

Welcome to Hiawatha’s Hideaway, a cozy 2BR, 1BA home in Ironwood, MI. Perfect for couples, families, groups up to 6, and remote workers seeking a peaceful nature retreat. Steps from the Hiawatha statue and near downtown, with easy access to hiking, ATV trails, alpine skiing, and snowmobiling. Stay productive with fast Wi-Fi and a dedicated workspace. Spacious yard with ample parking for trailers and toys.

Value · Family · Nearby