Holiday rentals in Winona

Cozy U.P. home conveniently located near trails.

A U.P. retreat that has everything you need with adventure at your fingertips. Come relax with your family and friends at our peaceful 3 bedroom home. It’s conveniently located near riding trails and offers 1/2 acre off road parking. It’s also less than a mile to a popular bar/restaurant. Greenland, Michigan has many things to explore with trails that go on for miles. A few examples nearby would be Adventure Mining Co., Lake Superior, Porcupine Mountains Ski Area and Lake of the Clouds.

Rustic cabin w/sauna on Portage Lk

Located on Portage Lake in Chassell, MI, near Houghton with quick access to Michigan Tech University, this rustic family cabin is a great place for either an overnight stay or a longer getaway. It provides a great home base for travel in the Keweenaw peninsula! As a 1930s cabin with a sauna on the lake along with a great view, the focus is on the experience! We find guests who truly enjoy our place are flexible with rustic conditions (not looking for Holiday Inn Express) and young at heart!

Guest Getaway Loft

Take a refreshing respite in the quiet or experience the bustle of historic downtown Calumet from our 500 sqft guest apartment. This studio apartment is lofted above the detached garage with a private entrance. Within walking distance of bars, restaurants, coffeehouses, bakeries, and local ski and snowmobile trails our guest home is a perfect place to explore all the Keweenaw peninsula has to offer. Guests have 24/7 access to the host, when necessary, as I live in the detached main house.

Cozy 2 bedroom home with a spacious back yard.

Come and relax in this cozy 2 bedroom home situated just off the main highway in Baraga, MI. The kitchen is equipped with oven/stovetop, refrigerator/freezer, coffee pot, toaster, microwave, assorted pots and pans, mixing bowls, measuring spoons and cups, flatware, cups, mugs, plates and bowls. In the living room sit and enjoy the Wifi or take advantage of the provided Netflix. On a nice evening enjoy some time around the backyard fire pit or grill out on the newly built back deck.

High Rock Cabin- 200 ft to trail 17! Close to town

Welcome to our “High Rock Cabin”. This centrally located tiny house is right by the trails. Set in the woods, but only a couple miles from Hancock/Houghton! One main floor bedroom with queen bed, and a loft with two full beds. Please be aware that there is a spiral staircase to access the loft. No smoking in cabin. Will be a $250 fee if smoking is detected. Also, pets must be approved by owners. Will entail an additional pet fee. There is plenty of parking, enough room for a trailer!

Quiet retreat on 18.5 acres for viewing wildlife.

Located on a dead-end gravel road, 1.5 miles to hard surface road. There is a house behind the cottage where one person lives. Construction completed in 2020, has a deck, a 2-acre pond, 15 acres cleared, woods to wander in, walking distance to Otter River, 19 miles to Houghton, 13 miles to Baraga on Lake Superior. Pricing is per bedroom, base price $125.00 for first bedroom for 1-2 guests per night, and an additional $75.00 for second bedroom per night when there will be 3-4 guests.

The Yooper Lodge! On the trail and close to lakes.

The Lodge is a great place to start your next adventure! It is centrally located to all the sights that the Western U.P. has to offer. Our place is a great base camp. The best trails and deep snow are as close as the front yard. Not to mention, trail #3 Bill Nicholls (one of the best in Michigan) is right across the road! Makes for great ATV and Snowmobile trips in all directions. There are restaurants, bars, and 2 gas stations/minimarts close by also.

Gateway to fun and adventure

Story and a half house on 33 acres of land. Sleeps 6. Fully furnished to be right at home. High speed fiber internet with WiFi, Roku TV, close to several lakes, streams, hunting land and trails. 10 miles to M26 /M38 snowmobile parking and 4 miles to the reopened 109 Alston trail. Awesome back road snowmobiling via Otter Siding Rd. Plenty of opportunities for fishing or hunting (33 acres private land) or hiking. Discounts on stays of 7 or more days.

Peaceful lakefront cabin with sauna, fenced yard

Lake Superior front cabin with large fenced yard, 2 main floor bedrooms and spacious bedroom loft, custom wood fired barrel sauna. Easy access off US41 between Baraga and Chassell in Michigan's beautiful Upper Peninsula. Fully appointed kitchen, full bath with tub/shower, washer and dryer and wood fireplace. A little piece of tranquil heaven on the greatest Great Lake! Dogs are very welcome! $25 dog fee