Photo by Frank Livermore

Search Vacation Homes in Upson

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

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

House in Bessemer - 3 BR/1.5 Bathrooms

9.8 out of 10, Exceptional, (102)
"A very welcoming, interesting, charming and cozy home. Comfortable for our group. Excellent directions and communication with the host. The home was warm, water pressure in the showers was excellent, no shortage of hot water for the five of us showering. Well equipped kitchen for all of our needs. Beds were comfortable. Everything was very clean. Wood burning fireplace was a welcome relaxing spot on this very cold weekend.I learned of the pet charge after booking. It is not unreasonable, less...
House in Bessemer - 3 BR/1.5 Bathrooms

Trail Riders Haven- Only 1 Block from TONS of Adventurous Trails! Huge Garage!

10.0 out of 10, Exceptional, (8)
"This was our second stay at this property and we will definitely be back. It is a favorite of ours in the area. They supply so many things, the rooms are so welcoming, and the heated garage is a plus. "
The price is AED 337
AED 1,028 total
includes taxes & fees
28 Jan - 29 Jan
Trail Riders Haven- Only 1 Block from TONS of Adventurous Trails! Huge Garage!

Cozy Corner Home Dogs Welcome

9.8 out of 10, Exceptional, (11)
"Had a nice stay for 3 days of skiing. Appreciated cleanliness of house and location close to ski resorts. Loved the thoughtful dog-friendly touches too. "
The price is AED 656
AED 1,570 total
includes taxes & fees
29 Jan - 30 Jan
Cozy Corner Home Dogs Welcome

Piper Haus Chalet Unit 1

10.0 out of 10, Exceptional, (22)
"Everything was great, the hot tub was a hit with the kids. There was plenty of room for our large group, having so many bathrooms was a plus. The host communication was spot on, I will definitely return next trip. Thank you for the hospitality. "
Piper Haus Chalet Unit 1

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

Lake house

9.4 out of 10, Exceptional, (6)
"Check in at 3 pm, I messaged manager three four times , finally I called by now it’s after 4, she sent door code promptly, and did apologize.It’s all good"
Lake house

Timeless Elegance-Modern Vintage Luxury

10.0 out of 10, Exceptional, (14)
"5 star rating….super clean, great location, nice beds, great layout, beautifully decorated. Will for sure stay again!! Thank you"
Timeless Elegance-Modern Vintage Luxury

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

9.8 out of 10, Exceptional, (29)
"Spacious 3 bedroom 2 baths lots of open space. Loved staying here to ski with our family. Board games, extra towels, bandaids, blankets galore. Much appreciated with sub zero wind chill skiing. Very well equipped kitchen with thoughtful extras! Thank you for sharing your home with us. Look forward to next trip!"
Tiny’s Retirement Home near the trails

Modern Family Style Getaway -Wakefield UP House for up to 8!

9.8 out of 10, Exceptional, (55)
"Very clean, close to great skiing"
Modern Family Style Getaway -Wakefield UP House for up to 8!

Charming 3-bedroom home in Ironwood with custom tiled showers. Dog-Friendly.

10.0 out of 10, Exceptional, (1)
"Tracy’s house is so comfortable, beautiful and enjoyable. They had anything you’d need in the kitchen and toiletries for the bathrooms. There was a winter storm. They came and plowed and shoveled during our stay. There were extra pillows and soft throw blankets everywhere. The beds were comfortable. The kitchen is beautiful. The bathrooms are very nice. It was a lovely home away from home. We will stay again. 10/10."
Charming 3-bedroom home in Ironwood with custom tiled showers. Dog-Friendly.

Swiss Hut Unit 2 New Listing

9.4 out of 10, Exceptional, (3)
"We come up two weekends per year to ski and this was a new place for us to stay this year. Will definitely try to stay here again."
Swiss Hut Unit 2 New Listing

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.

Vintage home located in Ironwood Michigan

8.6 out of 10, Excellent, (25)
"Home away from home."
The price is AED 367
AED 466 total
includes taxes & fees
27 Jan - 28 Jan
Vintage home located in Ironwood Michigan

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

Charming dog-friendly cabin with full kitchen, kayak, firepit & lake view

9.4 out of 10, Exceptional, (15)
"Nicely equipped kitchen, plenty of towels. Great Lake views Very difficult to negotiate lower path to lake and launch the kayaks. Very steep and rough. House is on a steep hill. Steps near the top are fine. Great fire pit with view in front of house."
Charming dog-friendly cabin with full kitchen, kayak, firepit & lake view

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!

Trailside Retreat #1 ~ Hot Tub & Trail #2 Access!

9.8 out of 10, Exceptional, (78)
"The place was immaculate, and set up with just about anything you might need during your stay. Definitely hope to be back soon."
Trailside Retreat #1 ~ Hot Tub & Trail #2 Access!

Grandpa Jim's Cabin - Close to The Gile Flowage/On ATV Route

10.0 out of 10, Exceptional, (14)
"Perfect little get away to unplug in the northwoods. Within driving distance of anything you could need or want to do"
Grandpa Jim's Cabin - Close to The Gile Flowage/On ATV Route

Cozy House w/Garage - Minutes to Trails & Waterfalls

10.0 out of 10, Exceptional, (26)
"The Cozy House was clean and perfect for our blended family. The younger children loved the beach and adventure rooms and our teen liked having the futon space. Check in was easy and the hosts were great communicators. We loved our waterfall and beach adventures - especially Little Girl’s Point! Thanks for helping us make great family memories!"
Cozy House w/Garage - Minutes to Trails & Waterfalls
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.
Don't see what you're looking for?
See all available properties in Upson
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Upson

House 2 - Gorgeous A Frame

10.0 out of 10, Exceptional, (18)
"This was a great little getaway. The space was great for our two families. Thank you"
House 2 - Gorgeous A Frame

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

9.4 out of 10, Exceptional, (6)
"Lots of room for everyone to be comfortable. Love the access to the ski hill. Super easy to check in. Beautiful view, we just love northern Wisconsin"
Upson Ski-In/Ski-Out, End-Unit Cabin w/ Fireplace!

House in Bessemer - 3 BR/1.5 Bathrooms

9.8 out of 10, Exceptional, (102)
"A very welcoming, interesting, charming and cozy home. Comfortable for our group. Excellent directions and communication with the host. The home was warm, water pressure in the showers was excellent, no shortage of hot water for the five of us showering. Well equipped kitchen for all of our needs. Beds were comfortable. Everything was very clean. Wood burning fireplace was a welcome relaxing spot on this very cold weekend.I learned of the pet charge after booking. It is not unreasonable, less...
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.