Vacation 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.

Tiny Home Glamping in the Keweenaw - 12 min to MTU

High-end glamping in the Keweenaw Peninsula. This tiny house/cabin features two lofts with queen-sized beds, a wood burning fireplace, dock with paddle boat on two acre pond, access to the Pike River and 20 acres of land for hiking and recreation. Cook in the kitchen or over the outdoor fire pit. Enjoy a wood-fired sauna and cool off with a dip in the pond. Bring a fishing rod and catch dinner out of the pond or the river! No running water but indoor composting toilet and a rain barrel/sink.

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.

JB Unique Bar Stay–SXS Trails, Firepit, Group Fun!

Jake’s Bed & Bar is a transformed historic bar turned 3-bedroom getaway in Michigan’s Western UP. Located on the trail and halfway between the Porcupine Mountains and Copper Harbor, it’s an ideal Adventure basecamp. 3 BR/1.5 bath/8 bed True bar, Wi-Fi & streaming TV Full kitchen, dishwasher, washer/dryer Fire pit, propane grill Karaoke, golf putt pong Pet friendly Trail access Easy access to lakes, waterfalls, beaches, and golf—park your trailer and ride straight from the property.

Rustic, yet Modern Trailside Cottage/MTU 2.3 Miles

Experience the Copper Country's natural beauty from our flagship property! The Miner was tastefully decorated & pays tribute to the area’s rich copper mining history. It is quaint & relaxing, yet spacious enough for entertaining. The Miner is the perfect destination for couples, business travelers and small families as it sits at the gateway to the Keweenaw and is located steps from the famed Jack Stevens snowmobile trail. A portion of all bookings will donated to local youth hockey.

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.

Kerban's Overlook

Nice, clean apartment just 5 minutes from Michigan Tech and a view of Portage Lake (lake access too!). One stall of garage parking available so you can go right from car to apartment without dealing with the snow. The driveway is plowed. Wifi, heat, keurig coffee selection included. Washer and dryer are in the spacious bathroom with a shower. Full kitchen and electric fireplace. Stairlift from garage. Queen sized bed with additional pullout couch (about full sz) and toddler bed.

Otter House

Otter House is a beautifully appointed log cabin in the trees overlooking Otter Lake. It is comfortably furnished with a well equipped kitchen. The lakefront has a small beach, 3 kayaks, a canoe, hammocks and a fire pit. Otter Lake is a tranquil spot with great fishing and very little boat traffic. Canoe up the Otter River or Kayak down to the dam. You will see eagles, beavers, turtles, loons, geese and if you're lucky an otter. There is a parking pad for your RV or trailer.

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.

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.

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