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103 Houses

(5) Excellent 

18

UPPER KASTENBOLE Chalet, Whitecap Mountain Resort

Wisconsin / Upson

Upson chalet

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 mi
  • Ski
“Nice comfy chalet in beautiful snow country!” We stayed in upper Kastenbole last February with three other couples. We found the rental rate very reasonable. Jeff and Lynn provide a wonderful chalet that is located within walking distance of the White
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Price per night from

$201

Price per night from

$201

Great rentals within 20 miles that match your search

Distance approx 18.15 km from Upson

17

Big Chalet on Big Powderhorn Mountain

Upper Peninsula / Bessemer

Bessemer chalet

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly

Price per night from

$200

Price per night from

$200

Distance approx 17.95 km from Upson

8

Mittenwald - Hot Tub 2 BR A-Frame Big Powderhorn

Upper Peninsula / Bessemer

Bessemer ski chalet

2 9 min stay varies

  • 2 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 17 mi
  • Ski
  • Child Friendly

Price per night from

$168

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$168

Distance approx 17.66 km from Upson

(18) Very Good 

28

Steamboat Fantasy

Upper Peninsula / Bessemer

Bessemer house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
“Great time!” Wonderful, clean condo with many extras and lots of room for large families. Kitchen well stocked with utensils and pots and pans providing the ability to make meals for large groups. Very close to Powderhorn Ski hill.
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Price per night from

$188

Price per night from

$188

Distance approx 18.19 km from Upson

(1) Very Good 

10

Snow Otter

Upper Peninsula / Bessemer

Bessemer chalet

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$294

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$294

Distance approx 18.02 km from Upson

(33) Excellent 

38

Bear Necessities

Upper Peninsula / Bessemer

Bessemer house

6 15 2 nights min

  • 6 bedrooms
  • sleeps 15
  • 2 nights min
  • Ask about children
“We love the Bear!” We love staying at Bear Necessities! The only downside was that the hot tub was rather dirty - old and sort of slimy water. But, the rest of the place was clean and spacious. We had a great stay.
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Price per night from

$336

Price per night from

$336

Distance approx 18.72 km from Upson

(1) Excellent 

24

Lakefront Mercer Cabin w/2 Lofts, Fire Pit & Porch

Wisconsin / Mercer

Mercer log cabin

1 8 min stay varies

  • 1 bedroom
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$146

Responds fast!
avg. 10 minutes

Price per night from

$146

Distance approx 16.73 km from Upson

(2) Very Good 

22

Five Star Cabin on Wolverine Trails - Sauna

Upper Peninsula / Ironwood

Ironwood house

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 17 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$202

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$202

Distance approx 18.22 km from Upson

(4) Excellent 

21

Piper Haus Unit 1

Upper Peninsula / Bessemer

Bessemer chalet

7 18 2 nights min

  • 7 bedrooms
  • sleeps 18
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$246

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$246

Distance approx 17.95 km from Upson

(27) Very Good 

23

Crossbow

Upper Peninsula / Ironwood

Ironwood house

4 13 2 nights min

  • 4 bedrooms
  • sleeps 13
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
“very nice, plenty of room” We really enjoy Crossbow. This waa our 2nd year renting the house and had more people than last year with plenty of room for everyone. The stove in the kitchen was updated in the past year and was a great improvement. The ho
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Price per night from

$227

Price per night from

$227

Distance approx 18.02 km from Upson

(14) Very Good 

22

Alps Villa 5

Upper Peninsula / Bessemer

Bessemer house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“review of lodge and service” the front doors needed lubricating they really squeak! tv's need better service but we were satisfied as that was not thereason we were there.Overall it was a really neat place to be
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Price per night from

$129

Price per night from

$129

Distance approx 18.02 km from Upson

(21) Very Good 

20

Alpine Villa 1

Upper Peninsula / Bessemer

Bessemer house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Wonderful stay at Alpen Powderhorn Resort Bessimer, MI” A very nice week was spent at Alpen at Powderhorn Resort in Bessimer MI. Everything at Alpen was wonderful, very nice place, quiet, clean, and very friendly staff. Hope to stay again!!!!
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Price per night from

$128

Price per night from

$128

Distance approx 12.52 km from Upson

34

Room 11

Upper Peninsula / Ironwood

Ironwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$76

Price per night from

$76

Distance approx 17.69 km from Upson

(25) Very Good 

26

Skyward

Upper Peninsula / Bessemer

Bessemer house

6 16 2 nights min

  • 6 bedrooms
  • sleeps 16
  • 2 nights min
  • Child Friendly
  • Pet Friendly
“Wonderful Powderhorn Vacation” We've stayed at Skyward three years now, and it is such a great location. The layout of the house is perfect for a few families to hunker down together and not feel on top of each other. Great place to stay!
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Price per night from

$404

Price per night from

$404

Distance approx 17.55 km from Upson

(28) Very Good 

19

Top Notch

Upper Peninsula / Ironwood

Ironwood house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
“20th anniversary with the family” My wife and I spent our honeymoon 20 yrs. ago at Big Powderhorn, in a quiet little a frame called the Tamarack 1 and this started a family ski trip that we repeated about 10 times over the past 20 years. We have spent
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Price per night from

$315

Price per night from

$315

Distance approx 17.76 km from Upson

(6) Very Good 

25

Christie Downs

Upper Peninsula / Ironwood

Ironwood house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Ask about children
  • Ask about pets
“Beautiful skiing and nice accomodations!” We rented Christie Downs for 3 nights. The house looked like the living area had some upgrades. The floor, couches and TV area was very nice. We were unable to get the gas fireplace to work. Bedrooms were dece
…see more

Price per night from

$283

Price per night from

$283

Distance approx 17.69 km from Upson

(15) Excellent 

24

Sno Summit

Upper Peninsula / Bessemer

Bessemer house

8 16 2 nights min

  • 8 bedrooms
  • sleeps 16
  • 2 nights min
  • Ask about children
  • Ask about pets
“Great place for great memories” How can you say that you had an "awesome" ski vacation when you are getting ready to ski at 9 a.m. and it is -27 outside? And we aren't talking wind chill here. How? Stay at Sno Summit and you will know why. We are
…see more

Price per night from

$336

Price per night from

$336

Distance approx 18.02 km from Upson

(11) Very Good 

21

Alps Villa 6

Upper Peninsula / Bessemer

Bessemer house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Great Time!” We were pleasantly suprised at our accomodations during our most recent ski weekend. The rental unit was clean and very inviting. The location was perfectly situated on the slopes. A great time was enjoyed by all. The only negative th
…see more

Price per night from

$129

Price per night from

$129

Distance approx 18.02 km from Upson

(11) Very Good 

29

Alpine Villa 2

Upper Peninsula / Bessemer

Bessemer house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Good location” Secluded from town. Has everything you for an extended stay. Nice and helpful staff. I have stayed at several of the other places at Powderhorn over the past 4 years and this one is the best.
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Price per night from

$128

Price per night from

$128

Distance approx 18.02 km from Upson

(4) Average 

24

Alps Villa 4

Upper Peninsula / Bessemer

Bessemer house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“great place” Place is great, we come up every year and stay at alpen Inn. I realized though, that with the large amount of people we come up with (20-25) we can find a better deal in other lodges. Alpen fits under 10 so we rent 3 units and there are
…see more

Price per night from

$128

Price per night from

$128

Distance approx 18.52 km from Upson

24

Pet-Friendly Downtown Bessemer House Near Skiing!

Upper Peninsula / Bessemer

Bessemer house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$151

Responds fast!
avg. 24 minutes

Price per night from

$151

Distance approx 18.27 km from Upson

(11) Very Good 

29

Tealwood

Upper Peninsula / Bessemer

Bessemer house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Great Stay!” We enjoyed our stay at Tealwood over the July 4th weekend. We had plenty of room and the chalet was stocked very well with everything you would need for a family gathering. The grill worked great and it was nice having an air conditioni
…see more

Price per night from

$189

Price per night from

$189

Distance approx 17.71 km from Upson

(2) Very Good 

20

Spacious 4 BR 2 bath Fireplace at Big Powderhorn

Upper Peninsula / Bessemer

Bessemer ski chalet

4 13 min stay varies

  • 4 bedrooms
  • sleeps 13
  • min stay varies
  • Nearest beach 17 mi
  • Ski
  • Child Friendly

Price per night from

$226

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$226

Distance approx 12.52 km from Upson

27

Room 5

Upper Peninsula / Ironwood

Ironwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$76

Price per night from

$76

Distance approx 12.52 km from Upson

26

Room 9

Upper Peninsula / Ironwood

Ironwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$76

Price per night from

$76

Distance approx 17.55 km from Upson

(6) Very Good 

25

Northern Lights

Upper Peninsula / Ironwood

Ironwood house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
“Snow Storm !” Best year ever with 18" of snow that weekend! Second year we've stayed at Northern Lights, large enough for our group. The shuttle bus drivers make your day. Best Bloody Mary's at the alpen Inn but the Brie appetizer is even better! Lov
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Price per night from

$290

Price per night from

$290

Distance approx 17.95 km from Upson

(8) Very Good 

24

Trailview 1

Upper Peninsula / Ironwood

Ironwood house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Ask about children
  • Ask about pets
“Awesome winter getaway!” We were so pleased with the Trailview 1 chalet. We had six adults and there was plenty of room for all of us. The living room was spacious and welcoming, and the fireplace was awesome (almost too hot sometimes!!) The kitche
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Price per night from

$173

Price per night from

$173

Distance approx 17.97 km from Upson

(1) Excellent 

9

Located at Big Powderhorn - 2 BR A-Frame - Hot Tub

Upper Peninsula / Bessemer

Bessemer house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 17 mi
  • Ski
  • Child Friendly

Price per night from

$201

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$201

Distance approx 17.65 km from Upson

18

Jacuzzi, Fireplace 2 BR 2 Bath at Big Powderhorn

Upper Peninsula / Bessemer

Bessemer house

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 17 mi
  • Ski
  • Child Friendly

Price per night from

$167

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$167

Distance approx 12.52 km from Upson

19

Room 21

Upper Peninsula / Ironwood

Ironwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$76

Price per night from

$76

Distance approx 17.76 km from Upson

(3)  

24

Blunderbuss

Upper Peninsula / Ironwood

Ironwood house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$172

Price per night from

$172

Distance approx 17.95 km from Upson

(9) Very Good 

24

Trailview 2

Upper Peninsula / Ironwood

Ironwood house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Ask about children
  • Pet Friendly
“Great summer getaway” The house was a great location for our UP adventures. Very roomy and the 2 full bathrooms was a plus with 6 adults. The only downfall was the rips in some of the screen windows, so most of them needed to stay closed.
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Price per night from

$172

Price per night from

$172

Distance approx 12.52 km from Upson

20

Room 20

Upper Peninsula / Ironwood

Ironwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$76

Price per night from

$76

Distance approx 17.72 km from Upson

(9) Very Good 

21

Sugar Pine

Upper Peninsula / Ironwood

Ironwood house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
“We love Sugar Pine!” We recently stayed at Sugar Pine, and truly enjoyed this cabin. We've been at other cabins on Powderhorn, and this one has become our new favorite. Bathrooms are roomy, love that it has 3 bathrooms. The main dining/kitchen/livi
…see more

Price per night from

$173

Price per night from

$173

Distance approx 12.52 km from Upson

33

Room 3

Upper Peninsula / Ironwood

Ironwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$76

Price per night from

$76

Distance approx 12.52 km from Upson

28

Room 7

Upper Peninsula / Ironwood

Ironwood room

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$76

Price per night from

$76

Distance approx 12.52 km from Upson

26

Room 2

Upper Peninsula / Ironwood

Ironwood room

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$74

Price per night from

$74

Distance approx 9.1 km from Upson

(18) Excellent 

30

Log Cabin Vacation Lodging near Hurley & Mercer WI

Wisconsin / Hurley

Hurley log cabin

4 13 min stay varies

  • 4 bedrooms
  • sleeps 13
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$201

Responds fast!
avg. 40 minutes

Price per night from

$201