Vacation rentals in Upson

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Top-rated vacation rentals in Upson

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Guest favorite

Home in Ramsay

4.97 out of 5 average rating, 119 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.

Sep 15 – 22

G$27,537 GYD per night

Guest favorite

Guesthouse in Sayner

4.97 out of 5 average rating, 152 reviews

Zen out & Sauna at LandsEndattheEdge Loft!

QUIET private zenny retreat! Covered deck in treetops overlooks NHAL state forest wilderness. Ponder a skyline of pines & a plethora of stars! Howling wolves & birdwatching; a vist by Woody, our resident pileated woodpecker sure to stop by. BBQ on gas grill, sit by firetable, or suhwing! Rustic sauna WIFI elect FP kitch 2kayaks. 5min to LostCanoe Lake, WhiteSand Lake BoatLaunch&Beach, Lumberjack/Escanaba StateTrls, 15min to HeartofVilas paved 52+mi Trl. Semi-secluded yet 8mi to BJ restaurants!

Sep 18 – 25

G$25,866 GYD per night

Guest favorite

Cabin in Ironwood

4.95 out of 5 average rating, 418 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.

Jun 6 – 13

G$21,104 GYD per night

Guest favorite

Guesthouse in Ashland

4.99 out of 5 average rating, 308 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.

Nov 23 – 30

G$39,388 GYD per night

Guest favorite

Home in Ironwood

4.99 out of 5 average rating, 215 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.

Jun 3 – 10

G$19,680 GYD per night

Guest favorite

Tiny home in Saxon

5.0 out of 5 average rating, 132 reviews

Parker Creek Tiny House

Come stay on our hobby farm with us! We have a great location only a few miles from ATV trails. There are a lot of great hiking trails and falls to visit in the area. We custom designed and built this home in 2020. We have a queen bed with an adjustable head and futon. It has in floor heating and a mini split to stay toasty warm in winter and cool in the summer. It has a washer and dryer, dishwasher, refrigerator and freezer, propane stove and oven, and microwave.

Mar 14 – 21

G$23,674 GYD per night

Guest favorite

Home in Ironwood

4.99 out of 5 average rating, 185 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!

Feb 11 – 18

G$27,502 GYD per night

Guest favorite

Bungalow in Ironwood

4.86 out of 5 average rating, 213 reviews

Quaint and Colorful Bungalow

My place is close to the main East-West Highway, but in a quiet neighborhood. It is near cross country ski trails, snowmobile trails, hiking trails, yet there are restaurants and dining within walking distance. You’ll love my place because of the neighborhood and the colorful coziness. It is easy to access from the road, or from the backyard. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Jun 16 – 23

G$22,550 GYD per night

Guest favorite

Guest suite in Rhinelander

4.99 out of 5 average rating, 100 reviews

Quiet Family Suite on River near Lakes and Trails

Family-size guest suite offers all the comforts of home within 15 min. of Minocqua, Rhinelander, and premier outdoor experiences. Inside find bright spaces, full log beams, and a hobbiton feel; open concept living area with fully stocked kitchen, table, bunk beds, large couch, TV and Wi-Fi; bedroom with queen bed and stowed air mattress; full bath; play room. Suite is fully enclosed with separate entrance from the attached private log house.

Sep 28 – Oct 5

G$23,385 GYD per night

Superhost

Yurt in Bayfield

4.96 out of 5 average rating, 287 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.

Sep 18 – 25

G$18,219 GYD per night

Superhost

Home in Montreal

4.9 out of 5 average rating, 143 reviews

Hilltop Acres

Hilltop Acres located in Historic Montreal, 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!

Jun 9 – 16

G$26,338 GYD per night

Guest favorite

Home in Ironwood

4.97 out of 5 average rating, 101 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.

Nov 17 – 24

G$32,132 GYD per night