Holiday rentals in Upson

4.92 out of 5 average rating, 104 reviews

Apartment in Ironwood

Downtown "Green Room" at Villages on Aurora

Welcome to our downtown getaway! Village on Aurora is located in the heart of downtown Ironwood putting you steps away from Ironwoods City Square and the Historical Ironwood Theater. Lake Superior is only a short drive North of Downtown leaving you minutes away from waterfalls, and beaches. Our area has a multitude of different types of trails (hiking, biking, cross country, snowmobile, ATV) many just steps from your front door. Electric car chargers are also available in the downtown area makin

4.93 out of 5 average rating, 104 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!

4.98 out of 5 average rating, 140 reviews

Home in Hurley

Cheerful, Charming Retreat

Enjoy a stylish experience at this centrally-located place; it’s a hidden treasure. Enjoy walking to restaurants, and adventure surrounding Hurley’s historic Silver Street while being able to retreat to a place of your own. Conveniently located close to the Iron Horse Trail. Waterfalls, skiing, kayaking, mountain biking are all adventures close by. Start your morning with a cup of coffee in the beautiful three-season porch, and end your day with your favorite drink under the glowing chandelier!

4.98 out of 5 average rating, 178 reviews

On the Trail-Cedar Sauna & Close to Ski & Trails

Our happy, extremely private little house sits on 2 lots & backs to the Iron Belle Trail! Minutes to Trails, Lakes & more. Updated floor to ceiling bringing a Light & Bright AZ-modern farmhouse vibe. Slate appliances inc a dishwater! farm sink, butcher-block countertops, coffee/Nespresso bar converted from orig owners 1894 stove, restored wood floors, 3 season porch w/ 1970's console & vinyls for your evening dance. Large deck & fire pit awaits your bottle of wine or cup of coffee.

4.95 out of 5 average rating, 108 reviews

Bungalow in Ironwood

HOT FIND *Powderhorn Porch* 4B/1BA dwntwn Bungalow

Welcome to the Powderhorn Porch! When you get off the trails or slopes there isn't a better place to come home to than this cozy 4BR/1BA bungalow located in downtown Ironwood just blocks from the trails. Long driveway to hold your vehicles and trailers. Centrally located to all that the Gogebic Range has to offer including 4 ski resorts, snowmobile trails, waterfalls, hiking, Porkies, Lake Superior, Copper Peak, and cute shops & restaurants. This home is perfect for your next trip to the UP!

4.96 out of 5 average rating, 515 reviews

Cabin in Ironwood

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.

4.97 out of 5 average rating, 252 reviews

The House Next Door, In-Town Two Story House

The House Next Door has a Northwoods feel while being in town and close to your likely destination. Just four blocks from downtown Ironwood, and in the heart of all the outdoor adventure the Gogebic Range has to offer. You'll love the warm cozy feel, and the ability to mingle in the open concept lr/dr/kitchen downstairs, or retreat upstairs for a quiet, peaceful setting. Individuals, couples, families, and up to eight friends would enjoy my place, provided you can live with one bathroom.

4.97 out of 5 average rating, 217 reviews

Tiny home in Saxon

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.

4.99 out of 5 average rating, 244 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!

4.93 out of 5 average rating, 238 reviews

The Cookie Cottage

Beautiful home built in 1930. Now newly remodeled with 4 bedrooms and 2 full bathrooms. Located 7 easy blocks from downtown Ironwood. One king bed, and 3 queen beds. Quiet neighborhood. Great launching point for any local activity. Nordic ski trails less then 4 miles away; downhill skiing, snowshoeing, road and mountain biking, kayaking and hiking are all very close by. Self check in but always available for help. Sorry no pets, and no events/parties allowed.

4.91 out of 5 average rating, 160 reviews

Home in Montreal

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!

4.91 out of 5 average rating, 215 reviews

Chalet in Bessemer

Hot Tub • Fireplace • Dog Friendly•Big Powderhorn

Located in the Village area of Big Powderhorn Ski Resort, this cozy A-frame offers comfort and convenience. Features include a covered HOT TUB to soothe your muscles at the end of a day of hiking, skiing or sledding. Close to Copper Peak, Lake Superior, waterfalls, bike trails and more. Inside you will find a wood FIREPLACE, 2 loft bedrooms with 4 beds, 1 full bath, fully equipped kitchen, Cable TV and WIFI. No cleaning fee!!!

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Other great holiday rentals in Upson

4.98 out of 5 average rating, 93 reviews

Travelers Haven: next to downtown and trails

LucasRating, 5 stars3 months ago

Anna's place was lovely. Ironwood always has a range from very cheap to quite expensive, so finding a middle ground accommodation that was clean, peaceful, and up to date was very much so enjoyed!

5 out of 5 average rating, 12 reviews

Cabin in Ironwood

*HOT TUB* 6 Mile Hideaway

EmmaRating, 5 stars2 weeks ago

Hannah’s place was gorgeous, comfortable, functional and clean. The location was amazing for nature lovers although we were just as happy relaxing at the house! I definitely plan to return in the future because we had such a great experience.

4.96 out of 5 average rating, 27 reviews

Cabin in Park Falls

Bolo's Landing (last home on peninsula)

KeyvanRating, 5 stars7 months ago

What a beautiful cabin on a secluded lake! I timed it perfectly to catch the magnificent foliage in full colour. Brian was incredibly helpful and proactive throughout my stay. Kayaking on the lake was a highlight, especially with a bald eagle soaring overhead for quite a while. The cabin itself was cosy and quick to warm up, making it the perfect retreat. Dawn’s muffins were excellent—highly recommended! Though my stay was brief, it was truly memorable. Thank you!

Chalet in Upson

4.85 out of 5 average rating, 47 reviews

AlpenhausWI Whitecap, Upson WI Waterfalls Hike Ski

CharlieRating, 5 stars4 months ago

Absolutely love this place! Colleen is an awesome host!

4.98 out of 5 average rating, 58 reviews

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

CaitlynRating, 5 stars2 weeks ago

We had an incredible weekend up north at The Beehive! 💛 We had a wonderful time with our family, enjoyed delicious food, and had a lot of fun. The place was remarkably clean, and the staff showed great care and preparation. The only downside was that Becky wanted to stop by during our reserved time, which would’ve disrupted our time at the beehive. Thankfully, she waited until checkout! Overall, I would love to return to The Beehive. It was a great place to spend the weekend with my family.

4.93 out of 5 average rating, 15 reviews

Flat in Ironwood

Blue Moon - Relax in Upgraded Comfort

DeannaRating, 5 stars3 months ago

The home was decorated nicely, plenty of kitchen pots, pans, and utensils to make a couple of nice meals. Very clean. Beds were comfortable! Plenty of towels and wash clothes. The bottled water in the fridge was very nice. Appreciated the flexibility of a little later check out. Would definitely stay again.