Holiday rentals in Upson

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Top-rated holiday rentals in Upson

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The living room showcases comfortable seating with a brown couch and a recliner, complemented by a light wooden coffee table. A decorative mirror, floor lamps, and wall art add character to the space. Natural light enters through large windows, enhancing the room's airy feel.
Home in Ironwood
4.99 out of 5 average rating, 228 reviews

Free Breakfst | Close 2 Ski Trails | 10% Off Ni Ra

❄️ PRIME LOCATION ❄️ Steps away from Mt. Zion Ski Hill, minutes from ABR, Wolverine ski trails, & dining. Five blocks north of US2, set amid peaceful surroundings, our cozy, immaculate, well-appointed home, provides a blend of comfort & convenience, ensuring your stay feels like home. ❖ What our guests say ❖ “Sue provides extra touches we’ve never experienced at another stay." “This was the best Airbnb I’ve ever stayed in & I’ve traveled the world.” 10% off nightly rate w/nonrefundable stay

Top guest favourite
A charming single-family home is surrounded by lush greenery and features a combination of wood and brick exteriors. A covered porch with decorative woodwork adds character, while large windows invite light into the space. The picturesque front yard is well-maintained and complements the overall curb appeal.
Home in Ironwood
4.94 out of 5 average rating, 120 reviews

Comfy Homebase for your Upper Peninsula Getaway

Centrally located 2 bed, 1.5 bath single family home all to yourself. Terrific floorplan with eat-in kitchen, large living + dining room with fireplace, 2 bedrooms and newly remodeled full bath. Powder Room on lower level. Just a few blocks to charming downtown Ironwood, Iron Belle Trail + close to Miners Park with trails for walking, mountain biking, snowshoeing, x-skiing. Quick access to all that’s amazing about the U.P.! If you love outdoor fun, this is the place to stay, relax + rejuvenate!

Guest favourite
A welcoming living room features two comfortable sofas and an armchair arranged around a central coffee table. Soft lighting from lamps and a hanging fixture illuminates the space, while natural light filters through windows adorned with light-colored drapes. A textured area rug anchors the seating area.
Home in Ironwood
4.96 out of 5 average rating, 166 reviews

Park Place - Updated Home Close to Downtown

Enjoy our freshly renovated, boho themed home near the heart of downtown Ironwood, MI featuring 2 bedrooms (1 King, 2 Queen & 1 Twin bed) & 1 bath with a beautiful soaker tub. Great starting point for any local activity. Walking, biking, ATV & snowmobile trails only a few minutes away in any direction. Self check in, but always available for help. As loving pet owners, we do allow up to 2 well-behaved dogs. Group event? Book the house next door too (up to 13 guests): airbnb.com/h/greenhaveniwd

Guest favourite
The home is situated on a spacious lot surrounded by trees, featuring large windows that allow natural light to fill the interior. Outdoor decks provide seating areas, ideal for enjoying the serene landscape. An additional building can be seen in the background.
Home in Hurley
4.97 out of 5 average rating, 153 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 favourite
A charming cabin with gray siding is nestled among snow-covered trees, illuminated by a warm light from the front door. A shoveling shovel is positioned by the entrance, and the surrounding area is blanketed in fresh snow, creating a serene winter atmosphere.
Cabin in Ironwood
4.96 out of 5 average rating, 559 reviews

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for hiking, biking, fishing, boating and everything in between. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

Top guest favourite
A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.
Guest house in Ashland
4.99 out of 5 average rating, 395 reviews

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

Top guest favourite
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, 268 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.

Top guest favourite
A charming A-frame chalet is surrounded by vibrant autumn foliage. The exterior features a blue metal roof and large windows that allow natural light to fill the interior. A wooden deck extends from the front, providing outdoor seating options, while a small shed is visible to the right.
Chalet in Bessemer
4.95 out of 5 average rating, 279 reviews

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

My place is located at Big Powderhorn Ski Resort and close to Lake Superior, family-friendly activities, great views, restaurants and dining. You’ll love my place because of the location, the ambiance, the outdoor space, and the neighborhood. My place is good for couples, solo adventurers, and families (with kids). Dog friendly! Outdoor Hot Tub! Wood burning Fireplace with wood supplied! Great cell service! TV, Cable, Roku, WIFI....great entertainment! Washer/Dryer

Top guest favourite
Home in Ironwood
4.99 out of 5 average rating, 290 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!

Guest favourite
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
4.91 out of 5 average rating, 172 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!

Superhost
A rustic red yurt is surrounded by a forest of trees. A large wooden deck offers a welcoming entrance and is equipped with a sturdy railing. Natural ground covers and underbrush can be seen nearby, creating a serene and natural setting.
Yurt in Bayfield
4.95 out of 5 average rating, 378 reviews

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

Top guest favourite
A spacious living room features a cozy sofa, a decorative table, and a work desk. Skylights provide abundant natural light, enhancing the soft color palette. Elegant art pieces and antique mirrors add character to the room, complemented by warm lighting fixtures and a welcoming atmosphere.
Loft in Ironwood
4.98 out of 5 average rating, 104 reviews

* New, Luxury* The Powerhouse Loft

The Powerhouse Loft Get ready to be wowed! Gorgeous, elegant, luxury loft in the heart of downtown Ironwood! Located on main street, in the Historic Lake Superior Power Company Building, this one of a kind space is a block from the Iron Belle Trail, minutes from multiple ski hills and cross country ski trails, steps away from downtown shops, restaurants and the Historic Ironwood Theatre!

Popular amenities for Upson holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Iron County
  5. Upson