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Compare 172 Vacation Homes in Upson with updated reviews, rates, and availability.

Cozy Home in Ironwood, MI
Living area
Cozy Home in Ironwood, MI
10.0 out of 10, Exceptional, (35)
"We stayed here to have a hub to check out some waterfalls. The place was great, zero complaints. "
The price is SAR 301
SAR 785 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Home in Ironwood, MI
Spacious 4 BR/2BA Home with Bar and Fenced Yard.
House Front
Spacious 4 BR/2BA Home with Bar and Fenced Yard.
9.8 out of 10, Exceptional, (24)
"Great house. Quiet neighborhood. Nice that it is just a few blocks from downtown. "
Spacious 4 BR/2BA Home with Bar and Fenced Yard.
House in Bessemer - 3 BR/1.5 Bathrooms
Street view
House in Bessemer - 3 BR/1.5 Bathrooms
9.8 out of 10, Exceptional, (96)
"2 geezer couples up for a relaxing weekend of fall color, hikes, and hanging out. House was comfy cozy, nicely laid out, had everything we needed at an attractive price. In and out easily, good access. Very good communication with Joe. House has one double bed so one couple ended up on twin beds, not a problem for us, we knew going in. Bottom line, enjoyed our stay, house was great. "
House in Bessemer - 3 BR/1.5 Bathrooms
Cheerful 4 bedroom house with a hot tub
Exterior
Cheerful 4 bedroom house with a hot tub
10.0 out of 10, Exceptional, (10)
"We rented this property for the weekend of my son's wedding in Bessemer, MI. I was looking for a place that would house all my family so we could all be together. This place met that need perfectly. The beds were comfy and the house was clean. I would definitely recommend this to family and friends. And the host always answered my questions in a timely manner. Thank you for a great stay!"
The price is SAR 1,875
SAR 2,254 total
includes taxes & fees
16 Nov - 17 Nov
Cheerful 4 bedroom house with a hot tub
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
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
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, (26)
"Very impressive overall give it a 10 plan on staying there again"
Tiny’s Retirement Home near the trails
Trail Riders Haven- Only 1 Block from TONS of Adventurous Trails! Huge Garage!
Exterior detail
Trail Riders Haven- Only 1 Block from TONS of Adventurous Trails! Huge Garage!
10.0 out of 10, Exceptional, (7)
"We had every thing we needed at this VRBO. The communication with the owner was excellent and the house was generally well stocked. It was close to all the activities that we wanted to do. I would definitely recommend this to friends and family and I would stay here again!"
The price is SAR 369
SAR 1,079 total
includes taxes & fees
16 Nov - 17 Nov
Trail Riders Haven- Only 1 Block from TONS of Adventurous Trails! Huge Garage!
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.
On the Trail-Cedar Sauna & Close to Ski & Trails
On the Trail-Cedar Sauna & Close to Ski & Trails
10.0 out of 10, Exceptional, (124)
"My family of four and I were looking for a place to stay for our UTV trip and this was the perfect spot! The location is excellent for easy trail access, yet it’s still a very quiet neighborhood. It’s also close to restaurants or places you’d need to go in town. The home was so clean and very tastefully decorated and remodeled. We just loved it! The vintage stereo/record player and the sauna were awesome perks. They have everything we needed for our stay. Melissa was very communicative and...
On the Trail-Cedar Sauna & Close to Ski & Trails
Piper Haus Chalet Unit 1
Outdoor dining
Piper Haus Chalet Unit 1
10.0 out of 10, Exceptional, (21)
"We booked this property in very short notice and afraid about the accuracy. But when we reached there, we were happy that we picked an excellent one. Host was reachable all the times and property had been located vert close to lot of scenic places and especially Copper peak site. We love to visit this place and stay in this property again during fall. "
Piper Haus Chalet Unit 1
Mountain View Home
Open Concept
Mountain View Home
10.0 out of 10, Exceptional, (6)
"The property is great, it has all the amenities of home. I’ve been coming up to the area for 5+ years and had always stayed at some of the local motels but this year I decided to do a VRBO"
Mountain View Home
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
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
Trailside Retreat #1 ~ Hot Tub & Trail #2 Access!
A day on the trail and a night in the hot tub!
Trailside Retreat #1 ~ Hot Tub & Trail #2 Access!
9.8 out of 10, Exceptional, (77)
"We had never stayed at a VRBO. This by far exceeded our expectations. This cozy house in a quiet neighborhood couldn’t have been a better experience. This house is so clean and comfortable. It has absolutely everything we needed. We could definitely stay here for a long time and be very content. The service was great also. We had an issue with the dishwasher and our maintenance man responded right away and was there the next morning. He was very friendly and helpful. I could go on and on how...
Trailside Retreat #1 ~ Hot Tub & Trail #2 Access!
Grandpa Jim's Cabin - Close to The Gile Flowage/On ATV Route
Property grounds
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 (Hurley, WI/Ironwood, MI area)
Exterior
Cozy House (Hurley, WI/Ironwood, MI area)
9.4 out of 10, Exceptional, (31)
"Quiet neighborhood, close to UTV trails, had everything we eere looking for."
Cozy House (Hurley, WI/Ironwood, MI area)
A Comfortable & Spacious Retreat in the Powderhorn Village
Property grounds
A Comfortable & Spacious Retreat in the Powderhorn Village
9.8 out of 10, Exceptional, (44)
"We had a great weekend with a group of friends. There were 9 of us, but could have comfortably fit more people. The kitchens were fully stocked and had all we needed for the weekend. We would highly recommend this house and hope to come back again next year! "
A Comfortable & Spacious Retreat in the Powderhorn Village
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, (17)
"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!
Black River Retreat (Dog Friendly!)
Black River Retreat (Dog Friendly!)
9.2 out of 10, Wonderful, (238)
"We enjoyed our stay. Hope to be back next year."
Black River Retreat (Dog Friendly!)
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.