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

Family · Location · Access

Lakefront Cottage

Escape to the peaceful Northwoods of Wisconsin. This 2‑bedroom cabin on Crystal Lake—perfect for a romantic weekend, solo retreat, or family vacation. You will have beautiful lake views, private water access, and kayaks & paddleboards. Take in the scenery from the indoor porch, private dock, or on the clear water. Start your morning with coffee and the call of loons. End your day watching unforgettable sunsets beneath rustling birches. Slow down, reconnect, and enjoy the beauty of lake life.

Location · Hospitality · Comfort

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!

Family · Location · Layout

Becky's Bee Hive: Clean, Cozy and Affordable!

The Bee Hive is a centrally located, family friendly, newly remodeled 1930's home that is conveniently located in a residential neighborhood on a corner lot with walking access to local businesses. Additional parking available on the side of the garage for multiple trailers and vehicles. The house is only a couple blocks from trails for biking, walking, ATVs and snowmobiling, within 2 to 15 minutes from ski trails and ski hills, and only 20 minutes from Lake Superior beaches and waterfalls.

Location · Family · Kitchen

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.

Family · Value · Amenities

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.

Family · Value · Walkability

!!Private Beach Access!! ~Cozy Lake Superior Cabin

This cozy Lake Superior cabin sleeps up to 7 guests. Enjoy your own private beach (a rock collector's paradise!) or head over to Little Girls Point, Superior Falls, & Saxon Harbor all located within ~6 miles! 20 min from downtown Ironwood/Hurley. Take the paddle board for a spin and enjoy a bonfire with beautiful sunset views like you've never seen before. This stay is perfect for a relaxing couple's getaway or a lively family vacation. Keyless entry makes for quick & easy access!

Location · Family · Getting around

3 BR l Lakefront Cabin l

Welcome to your very own slice of paradise at The Lighthouse! We know how important it is to find a space that feels both comfortable and inviting, and that’s exactly what we’ve crafted here just for you. As seasoned travelers ourselves, we’ve poured our hearts into every detail to ensure your stay is nothing short of amazing. So, what are you waiting for? Dive into the tranquility of this magical place and book your stay at The Lighthouse now – we can’t wait to host you!

Family · Location · Nearby

Bakery Bunkhouse - Sweet Amenities & Nature !

Yooper Delights Baking Co. is now a family style home with beds for 7 ppl, a large, fully stocked kitchen, Scandinavian cottage design with 2 sleeping lofts plus a queen sleeper on main level, oak dining table for 8, Swedish gas fireplace, patio doors to back yard with firepit, gas grill & relaxing patio for outdoor dining & watching our visiting deer! We are located 2 miles from town, on outskirts, semi rural & peaceful , close to trails & Lake Superior!

Location · Value · Quiet

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.

Family · Location · Nearby

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.

Family · Value · Walkability

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!

Family · Value · Grill