Vacation rentals in Upson

The Snuggery @ Whitecap ~ Ensuite Sauna *Now with

Get ready for amazing views and cozy nights by the wood burning fireplace at the newly updated Snuggery! Located in the Whitecap Ski Village, this 3+ bedroom, 2 baths home is the perfect year round base camp for all of your outdoor adventures! Complete with an ensuite electric sauna, air conditioning, large wood burning fireplace, fully stocked kitchen, coffee bar and 2 large exterior decks, the Snuggery has everything you need to make your time away extra special! Aside from the amazing Whitec

Becky's Bee Hive: Clean, Cozy and Affordable!

The Bee Hive is a centrally located, family friendly, newly remodeled 1930's home that is conveniently located in a residential neighborhood on a corner lot with walking access to local businesses. Additional parking available on the side of the garage for multiple trailers and vehicles. The house is only a couple blocks from trails for biking, walking, ATVs and snowmobiling, within 2 to 15 minutes from ski trails and ski hills, and only 20 minutes from Lake Superior beaches and waterfalls.

Cozy Home onTrail|Sauna|PetsI Lakes Trails Falls

Welcome to Little House on The Trail!—perfectly located near the Porcupine Mountains, Lake Superior, waterfalls and hiking trails. This spotless, thoughtfully designed home blends vintage charm with modern comfort, featuring a fully stocked kitchen & coffee bar. Unwind in the cedar sauna or gather around the firepit. Pets ok, spacious, and packed with amenities, it’s the perfect Northwoods getaway year-round. ⭐ Guests consistently say this is the best Airbnb they’ve stayed in—come see why!

Bolo's Landing (last home on peninsula)

Modern comfort meets rustic charm at Bolo’s Landing on Muskie Lake. With direct trail access, a private pier, kayaks, and stunning lake views, it's your perfect Northwoods getaway year-round. We have room for your trailer and are just off of Iron County Trail 8 and 8a. Enjoy the almost 100-acre PRIVATE lake with included kayaks and rowboat (with life jackets). Cooking your thing? Just bring your food we have the rest. If not, there are 7 restaurants (bar scene to gourmet) within 13 miles.

Sylvan Chalet, Modern, Lakefront, Close to Trails

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind. Cabin is brand new as of January 2024. Host is 14 year "superhost" This is a default "no pets" cabin, however certain sizes and breeds are allowed by permission only. We have a NEMA 15-40R outlet for level 2 EV charging. You bring chord and adapter

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

"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!

Copper Falls Cabin

Copper Falls Cabin sits on 80 acres directly adjacent to Copper Falls State Park near Mellen, WI. The renovated rural farmhouse features 4 bedrooms and 1.5 baths. Copper Falls State Park is right out your door, and places like Bayfield and the Apostle Islands National lakeshore are within an hour’s drive. This is your perfect basecamp to explore the South Shore of Lake Superior in both Wisconsin and the western Upper Peninsula of Michigan.

Hilltop Acres - Hike-Bike-Ski-Sled-ATV-Hunt-Fish

Hilltop Acres located in Historic Montreal, WI, just 3 miles from Hurley, 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!

Wildlife Cabin in Mercer

Built in 2022/2023 this cabin is located right on the Manitowish River with 750ft of frontage right off Highway 51 about 3 miles south of Mercer and 7 miles north of Manitowish Waters. The Manitowish River runs into the Bear River which is why the resort is named Twin Rivers Resort. We are located right by the snowmobile, UTV/ATV and hiking/biking trails. You can easily visit small local towns with bars, restaurants and shopping.

The Saari House on the ABR Ski Trails

The Saari House is a fully updated farmhouse located on the ABR ski trails. Ski on the freshly groomed trails right out the front door. (Trail passes required.) It's a perfect location for families skiing in and out on a winter getaway or as home base for local waterfall hiking or biking. Guests will have full kitchen, bathroom with tub/shower, washer/dryer, TV with collection of DVDs, various video games and board games.

Stunning 3 bed, 2 bath private lake front cottage.

Take it easy at this unique and tranquil getaway. All season property in wooded setting. Ski-in/ski-out access to Whitecap Mountain, snowmobile trails and ice fishing. Cottage is nestled on the hills of whitecap Mountain overlooking Weber Lake where you can kayak, swim or fish. Winter access requires 4 wheel drive. Public use of the indoor pool for a nominal daily fee in the Whitecap hotel is available nearby.