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Compare 174 Vacation Homes in Upson with updated reviews, rates, and availability.

House in Bessemer - 3 BR/1.5 Bathrooms
A snow lover's paradise!

House in Bessemer - 3 BR/1.5 Bathrooms

9.8 out of 10, Exceptional, (99)
"Great to have room and privacy while staying in Big Snow Country"
House in Bessemer - 3 BR/1.5 Bathrooms
Vintage home located in Ironwood Michigan
Exterior

Vintage home located in Ironwood Michigan

8.8 out of 10, Excellent, (24)
"Home away from home."
Vintage home located in Ironwood Michigan
On the Trail-Cedar Sauna & Close to Ski & Trails

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

10.0 out of 10, Exceptional, (127)
"Wonderful, cozy and very clean. Perfect location to downtown and ski trails."
On the Trail-Cedar Sauna & Close to Ski & Trails
Winter has returned to Big Snow Country!!
Exterior

Winter has returned to Big Snow Country!!

10.0 out of 10, Exceptional, (9)
"Well appointed quaint farm house very warm and cheery place to be."
Winter has returned to Big Snow Country!!
Main Level Cozy Home, Conveniently located near downtown by Lakes & Trails.

Main Level Cozy Home, Conveniently located near downtown by Lakes & Trails.

9.8 out of 10, Exceptional, (6)
"property was clean and as described walking distance to bars and grills gas station.grocery store and dg within a mile.we had truck trailer and two sxs it was a little tight but 2 of 3 neighbors were very friendly and helpful 1 house away from off road trails all in all it was perfect for what we wanted"
Main Level Cozy Home, Conveniently located near downtown by Lakes & Trails.
Cozy Corner Home Dogs Welcome
Front of house with snow!

Cozy Corner Home Dogs Welcome

10.0 out of 10, Exceptional, (9)
"Had a bit of trouble with VRBO and Jen was amazing to work with! She also understands the importance of families traveling with pets and welcomes them with an accommodating home for them. Perfect set up when traveling with pups! The house is clean, well stocked, comfy beds and pillows, wifi, streaming options. Only a few blocks from trail 2 for snowmobiling. We will definitely return for a stay!"
The price is SAR 670
SAR 1,518 total
includes taxes & fees
21 Jan - 22 Jan
Cozy Corner Home Dogs Welcome
THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL
Multi-Tier Deck just 100 feet from Lake Michele/Lablonde Flowage.

THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL

9.6 out of 10, Exceptional, (22)
"This was a great place to stay. Rooms were nice!"
THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL
Trails Edge Escape- On the Ironwood/Hurley Border
Exterior

Trails Edge Escape- On the Ironwood/Hurley Border

10.0 out of 10, Exceptional, (6)
"great experience"
Trails Edge Escape- On the Ironwood/Hurley Border
Tiny’s Retirement Home near the trails
Private kitchen

Tiny’s Retirement Home near the trails

9.8 out of 10, Exceptional, (28)
"The cabin worked great for our hunting party."
Tiny’s Retirement Home near the trails
Mountain view Chalet with fireplace and sauna
Snow Otter Haus Upper Unit

Mountain view Chalet with fireplace and sauna

9.8 out of 10, Exceptional, (7)
"Very clean and host thoughtful of your needs. Provided popcorn that was perfect to watch TV."
The price is SAR 528
SAR 1,240 total
includes taxes & fees
12 Jan - 13 Jan
Mountain view Chalet with fireplace and sauna
2 Min to Big Powderhorn Lodge & Lifts! ~ Drift-Away Lodge 3
Living area

2 Min to Big Powderhorn Lodge & Lifts! ~ Drift-Away Lodge 3

10.0 out of 10, Exceptional, (4)
"My family and I enjoyed our stay. The condo was clean and well equipped. Comfortable beds. Conveniently located to Ironwood, Bessemer, and hiking trails."
The price is SAR 1,044
SAR 1,943 total
includes taxes & fees
11 Jan - 12 Jan
2 Min to Big Powderhorn Lodge & Lifts! ~ Drift-Away Lodge 3
Swiss Hut Unit 2 New Listing
Living area

Swiss Hut Unit 2 New Listing

10.0 out of 10, Exceptional, (1)
Swiss Hut Unit 2 New Listing
Dog-friendly lakefront home with a private beach, dock, firepit, & kayaks

Dog-friendly lakefront home with a private beach, dock, firepit, & kayaks

9.4 out of 10, Exceptional, (11)
"W the welcoming calls of loons from crystal clear Grand Portage Lake. What a wonderful stay! The cottage was beautifully appointed. The ample outside spaces provided postcard views. Located close to grocery, downtown restaurants and the Heart of Vilas bike trail head, we could not have enjoyed our stay more and look forward to our visiting again soon."
Dog-friendly lakefront home with a private beach, dock, firepit, & kayaks
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Property grounds

North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.

9.6 out of 10, Exceptional, (11)
"This was a nice location with a great view "
North Fork Flambeau River near Park Falls, 3BR, 1BA country home, on ATV route.
Lakefront dog-friendly gem with private dock, wood stove, large deck & free WiFi

Lakefront dog-friendly gem with private dock, wood stove, large deck & free WiFi

8.4 out of 10, Very Good, (34)
"Beautiful home and views. Took full advantage of the kayaks and lake. Loved the launch on the pier. Will definitely put on list of places to come back to"
Lakefront dog-friendly gem with private dock, wood stove, large deck & free WiFi
Lake Rd Abode-Game Rm-Central AC-Close to Trails/Lakes

Lake Rd Abode-Game Rm-Central AC-Close to Trails/Lakes

10.0 out of 10, Exceptional, (91)
"Our second stay at this beautiful house! Michelle is wonderful to deal with and the house she has created makes you look forward to coming home from the days adventure! So many amenities, great location and just a beautiful part of Michigan. We will be back❤️"
Lake Rd Abode-Game Rm-Central AC-Close to Trails/Lakes
Enjoy the Great Outdoors and Lake Superior
Ski House 10 Summer

Enjoy the Great Outdoors and Lake Superior

9.8 out of 10, Exceptional, (36)
"House was as described and exactly what we were looking for. Lots of beds, clean and in the right area. Main areas are a little cozy but worked for us and are as listed. Communication with the host was good. Thanks for a nice stay. "
Enjoy the Great Outdoors and Lake Superior
History-filled lakefront home with dock, fire pit, fireplace, & kayaks - dogs OK

History-filled lakefront home with dock, fire pit, fireplace, & kayaks - dogs OK

9.6 out of 10, Exceptional, (17)
"Very nice and accommodating place to stay."
History-filled lakefront home with dock, fire pit, fireplace, & kayaks - dogs OK
Becky's Bee Hive, Clean, Cozy, Affordable and Family Friendly!
seasonal livingroom space

Becky's Bee Hive, Clean, Cozy, Affordable and Family Friendly!

10.0 out of 10, Exceptional, (19)
"Beautiful home with everything needed for a long ski weekend. Cute decor with the Bee Hive theme. Thoughtful welcome gift and loved the condiments, coffee, creamer that was provided. Super clean! "
Becky's Bee Hive, Clean, Cozy, Affordable and Family Friendly!
Ironwood Trailside Adventures
Room

Ironwood Trailside Adventures

10.0 out of 10, Exceptional, (14)
"We loved how comfortable and well stocked the house was. Great location for what we wanted to do - hike to waterfalls and scenic vistas, see Northern Lights along Lake Superior, tour Stormy Kromer factory, and eat out."
Ironwood Trailside Adventures
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Upson

House 2 - Gorgeous A Frame
Exterior

House 2 - Gorgeous A Frame

10.0 out of 10, Exceptional, (18)
"Our overall stay was very comfortable and fun. This A frame cabin is cute on the inside. We loved that there was an area outside to be able to sit and have a bonfire. Would highly recommend this as a place to stay, "
House 2 - Gorgeous A Frame
Upson Ski-In/Ski-Out, End-Unit Cabin w/ Fireplace!
Upson Vacation Rental | 4BR | 3BA | 1,622 Sq Ft | Stairs Required

Upson Ski-In/Ski-Out, End-Unit Cabin w/ Fireplace!

9.2 out of 10, Wonderful, (5)
"We were happy with the amenities of the home and especially the end unit location. So easy to snowboard right out the back door to the lift! This spot also provides more parking spots than the other units on the side of the building. The townhome was entirely more than enough room for 4 adults and our dogs. Love having 3 full bathrooms! The best part was that we were able to extend our stay easily by texting the owner and got a quick response! We were able to enjoy an entire extra day on the...
Upson Ski-In/Ski-Out, End-Unit Cabin w/ Fireplace!
House in Bessemer - 3 BR/1.5 Bathrooms
A snow lover's paradise!

House in Bessemer - 3 BR/1.5 Bathrooms

9.8 out of 10, Exceptional, (99)
"Great to have room and privacy while staying in Big Snow Country"
House in Bessemer - 3 BR/1.5 Bathrooms
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.