Holiday houses in Upson

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!

4.97 out of 5 average rating, 153 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

4.98 out of 5 average rating, 141 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!

4.87 out of 5 average rating, 149 reviews

Tent in Ironwood

Off grid glamping at a Rockhound Hideaway

A perfect glamping retreat awaits you at Rockhound Hideaway's Agate Grove Bell Tent. Situated on a private two acre lot with two other rentals and my private residence in the Ottawa National Forest, steps from the Black River, North Country Trail and a one mile walk to the Lake Superior Shore, this is an ideal getaway for those seeking the adventure of camping with the comforts of home. Fall asleep to the sound nature and wake up to deer passing by as you enjoy your morning coffee.

4.96 out of 5 average rating, 263 reviews

Home in Ramsay

TINY Home - BIG Adventures - Hike/Bike/Ride

Couples retreat! Self check in to our Tiny Home with a door code and let the Big adventures begin! Only minutes from Indianhead, Blackjack, Big Powderhorn & Mt. Zion ski hills. A bit further away, but worth the drive, are Whitecap Mountain and Porcupine Mountains. Also, close to ABR x-c skiing, the Iron Belle Trail, and Lake Superior. Winter Hikes are beautiful in the U.P. Bring your fur babies along for a winter hike to the Porkies, Lake of the Clouds or Black River Scenic Byway.

4.97 out of 5 average rating, 219 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, 245 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!

4.95 out of 5 average rating, 63 reviews

Cottage in Upson

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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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!

4.89 out of 5 average rating, 35 reviews

Chalet in Upson

Mineshaft Chalets 2 at Whitecap Mountain Resort

CindyRating, 5 stars10 months ago

We had plenty of room for our entire family. The lake and surrounding area is beautiful with great proximity to Lake Superior and lots of trails. We would stay here again.

5 out of 5 average rating, 12 reviews

Cabin in Ironwood

*HOT TUB* 6 Mile Hideaway

EmmaRating, 5 stars3 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.

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!

Superhost

Cabin in Mercer

5 out of 5 average rating, 4 reviews

*Brand*NEW*Trailside Retreat w/ Sauna+Game Room

SarahRating, 5 stars1 day ago

From the moment we pulled in we knew we were going to enjoy this beautiful oasis. We absolutely loved the layout and the peace and quiet. The fire pit was great, remember to bring wood. We are already looking forward to returning soon. Thank you!

4.86 out of 5 average rating, 58 reviews

Apartment in Hurley

Hurley, 1 block from Famous Silver Street

DarylRating, 5 stars3 months ago

Great location right off the snowmobile trail and close to downtown. Nice big parking lot for a snowmobile trailer. House was clean and comfortable. Everything was as described.

4.94 out of 5 average rating, 32 reviews

Home in Hurley

A Stunning 2 bed/1bath, Hurley,Mercer UTV, Lakes

AaronRating, 5 stars8 months ago

Perfect cozy cabin tucked away in a wooded lot. Kitchen and bathroom were both large and nicely updated with new appliances and fixtures. We stayed there for our annual fall atv ride and the huge driveway and trail access across the street did not disappoint! Only minutes from downtown Hurley, it was a great location for a weekend getaway.