Vacation rentals in Upson

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Top-rated vacation rentals in Upson

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Guest favorite
Chalet in Upson
4.94 out of 5 average rating, 16 reviews

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

Guest favorite
Home in Hurley
4.96 out of 5 average rating, 161 reviews

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!

Top guest favorite
A sitting area features a futon draped with a cozy blanket, complemented by colorful accent pillows. A spacious bed with a patterned coverlet is positioned nearby, while a countertop with bar stools creates an inviting space for dining or gathering.
Tiny home in Saxon
4.97 out of 5 average rating, 308 reviews

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.

Guest favorite
A dining area features a round wooden table surrounded by four chairs, enhancing the inviting space. A cozy seating area is visible in the background, with a comfortable chair and a television mounted on the wall. Natural light filters through the window, illuminating the space.
Home in Ironwood
4.92 out of 5 average rating, 66 reviews

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

Guest favorite
A tranquil campfire area is set near Lake Superior, featuring a fire pit surrounded by wooden benches and chairs. The scene is framed by trees, with the lake and a sunset in the background, creating a serene outdoor gathering space.
Cabin in Ironwood
4.99 out of 5 average rating, 80 reviews

!!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!

Top guest favorite
A modern cabin is set among tall trees, featuring a spacious wooden deck with stairs leading up to it. Large windows offer views into the interior, while warm lighting creates a welcoming atmosphere as dusk approaches.
Cabin in Park Falls
4.91 out of 5 average rating, 112 reviews

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.

Top guest favorite
Home in Ironwood
4.99 out of 5 average rating, 338 reviews

"Bakery Bungalow" -Sweet Accommodations & Nature !

Completely remodeled from head to toe! Located within half mile of trail system, 2 miles from historic downtown shops, on the outskirt of town (Ironwood Township=great drinking water) minutes from Big Powderhorn Mountain & Copper Peak, walking distance to Gogebic College & Mount Zion, 17 miles from Lake Superior, large private wooded yard with fire pit in summer, private parking, 1 stall garage if needed in winter. A light Bakery breakfast included with your stay!

Top guest favorite
A bright living area is highlighted by large windows offering a view of the serene lake. Two comfortable armchairs sit beside the windows, while dark curtains frame the light-filled space. A dark leather sofa is positioned opposite, enhancing the cozy atmosphere.
Cabin in Mercer
5 out of 5 average rating, 23 reviews

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.

Guest favorite
A spacious farmhouse exterior is presented, featuring a welcoming front porch adorned with wooden railings. Lush greenery and blooming white hydrangeas enhance the landscape, alongside a well-maintained lawn. The structure includes a combination of siding and a metal roof, surrounded by trees.
Home in Highbridge
4.92 out of 5 average rating, 39 reviews

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.

Top guest favorite
A charming two-story house is set on a spacious lawn, surrounded by trees. The front features a welcoming porch with steps leading up, and an American flag is displayed. A small garage is attached to the side, with natural light filtering through the surrounding greenery.
Home in Montreal
4.92 out of 5 average rating, 188 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!

Top guest favorite
A charming farmhouse features a white exterior with a gabled roof and multiple windows. Snow blankets the ground, highlighting the entry steps. A wreath decorates the front door, framed by snow-covered shrubs, while a clear blue sky completes the winter scene.
Home in Ironwood
4.95 out of 5 average rating, 129 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.

Top guest favorite
A wooden cottage is set amongst lush greenery, featuring a spacious wrap-around porch and a covered entrance. The structure is elevated with a flight of stairs leading to the porch, and a gravel driveway provides accessible parking beside it.
Cottage in Upson
4.96 out of 5 average rating, 81 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.

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