Holiday rentals in Winona

SH Lake Escape w/Kayaks, Canoe, Firepit, Fishing

Escape to Sunsets, swimming, kayaks, snowmobile & ATV trails. Our charming 2 bedroom house situated on Sandy Lake frontage, nestled in a serene cove just off the main lake. Fire pit w/wood Grill & Outdoor dining Lead cable for dogs WiFi w/Streaming Full kitchen w/ dishwasher & keurig Washer/dryer 2 Fullsize Kayaks, 1 childrens kayak, Paddleboat, and Rowboat All the true amenities of a perfect vacation! We offer varied pricing by day/season making it easy for you to plan your perfect vacation.

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!

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.

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.

Country Home in Michigan's U P

Relax in our ranch style house next to our beef farm in Toivola, MI. See the cows in the fields. Enjoy a quiet relaxing day, play games in the yard, build a campfire or check out the stars at night or the beautiful fall colors. Close to Michigan Tech Univ., Mine tours, Waterfalls and other Historical Landmarks. Visit Lake Superior just 6 miles away. Pick Agates or Yooper Lights at Agate Beach. Ride the ATV / Snowmobile trails from Copper Harbor to the Porcupine Mountains.

Lake Superior Get-Away

This Lake Superior cottage is perfect for an up north get-away. Enjoy the breathtaking sunsets, strolls along the beach, swimming, kayaking or making your evenings memorable by sitting around the fire pit getting lost in the flames. This Northwoods style home is located 10 minutes from the spectacular Porcupine Mountains. 186' privately owned beach property. At 400 sq ft of living, it comfortably sleeps four with one bedroom and loft area. Two Kayaks are complimentary.

Hancock Old Mining House (Duplex)

Upstairs half of duplex in Hancock. This mining era house was converted to a duplex somewhere along the way. The living space is completely private but there is a shared entrance with the lower unit on the front porch. Our co-host Shelby lives in the lower unit. This Airbnb listing not a luxury rental It's an old but clean, functional apartment that is ideal for one to two quiet guests. We purchased house in 2021 and lived in the lower unit until March of 2024.