Vacation rentals in Upson

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Top-rated vacation rentals in Upson

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

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Guest favorite

Home in Ramsay

4.96 out of 5 average rating, 148 reviews

Happy Hippie Shack! Good U.P. Vibes Hike/Bike/Ride

Hippies Retreat!! Self check in with a door code and let the Good Vibes and Adventures begin! Our place is designed for guests with an open mind, free spirit and great Hippie sense of humor. You will have a Groovy pad to land after exploring the U.P. and are 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.

Guest favorite

Home in Hurley

4.98 out of 5 average rating, 129 reviews

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!

Guest favorite

Guesthouse in Sayner

4.98 out of 5 average rating, 177 reviews

Sauna Snowshoe&Pinely Peace-Lands End at Edge Loft

QUIET PRIVATE zenny retreat with large screened-in deck overlooks NHAL wilderness. Ponder a pine skyline & a plethora of stars! Howling wolves, a floodlight so you can watch it snow at night. Gas grill, firetable. Rustic SAUNA. WIFI, elect FP, kitch, 2 PAIR SNOWSHOES & a trail out the door. LostCanoe Lake, WhiteSand Lake BoatLaunch&Beach, Escanaba & Lumberjack St Trails in 5min. HeartofVilas paved Trl, Fallison Lake St Trl 20min. RusticRd #60 on the way. Semi-secluded yet 8mi to BJ restaurants!

Guest favorite

Home in Ironwood

4.99 out of 5 average rating, 165 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.

Guest favorite

Cabin in Ironwood

4.95 out of 5 average rating, 473 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.

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 349 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.

Guest favorite

Chalet in Bessemer

4.93 out of 5 average rating, 114 reviews

Rustic Chalet near hiking-biking-waterfalls-trails

Come enjoy this cozy and clean duplex chalet with jet tub! New pillows, sheets, and bath towels. This chalet is located steps from the base of Big Powderhorn Mtn resort, so no need to drive. You can snowmobile/ATV right from the chalet to trail #2, which is a few minutes away. The chalet is close to many beautiful waterfalls. The fully stocked kitchen with crock pot so food can cook while you are out having fun. Ninja coffee maker & grounds provided. 50" & 32" smart TV, WIFI, and A/C!!

Guest favorite

Tiny home in Saxon

4.98 out of 5 average rating, 194 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.

Superhost

Condo in Ashland

4.91 out of 5 average rating, 102 reviews

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

Guest favorite

Home in Ironwood

4.99 out of 5 average rating, 211 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 favorite

Home in Ironwood

4.94 out of 5 average rating, 218 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.

Guest favorite

Home in Montreal

4.9 out of 5 average rating, 153 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!