Holiday rentals in Winona

"Northbound" Secluded Cabin in Keweenaw Penninsula

Your Keweenaw adventure begins here! This centrally located cabin seated on a private 6-acre lot provides easy access to local favorites such as Copper Harbor, Mt Bohemia, Mt Ripley, Lake Superior, 1.5mi from UP17, and 3mi from UP13 ATV/snowmobile and bike trails. Close to many public boat ramps.Equipped with a full kitchen and living room, this cabin sleeps up to six people with a full bath. Ample parking for ATV/snowmobile trailers. The cabin is a short drive to Calumet, Hancock, and Houghton.

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

Stay in the heart of Western UP at our transformed historic Jake's Bed & Bar! This 3 bedroom property is located right on the trail and halfway between Porcupine Mountains and Copper Harbor. 8 beds Fire Pit w/wood Propane Grill Wifi & Streaming TV Cornhole Karaoke Machine Golf Putt Pong A true bar in your living room Full kitchen, Washer/Dryer, Dishwasher Enjoy countless activities like lakes, waterfalls, beaches, biking, and golf. This property offers easy access to the Western UP trail system

Twin Lakes Recreation Get-a-way

Enjoy the UP at this secluded property with 25 private acres in the resort area of Twin Lakes. Snowmobile or ATV directly to Trail 3. Explore abandoned copper mine on the property. Hike to local waterfalls or take an underground mine tour. Hit the water at Twin Lakes State Park. Golf at Wyandotte Hills. Enjoy a meal and refreshment at Boondock Inn or Parkview Lodge & Grill. Gas & groceries at Krupp's Mini Mart or 4 Seasons Convenience. All these stops within a few miles of the house.

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.

Perfect Couple's Get-Away with Private Beachfront!

Rock Beach-182’ of Lake Superior shoreline is your beachfront get-away! Search for agates, pick beach glass, kayak, fish, cycle along the shore, explore waterfalls, back roads, and sandy beaches! Participate in many local events-summer concerts, fishing tournaments, waterfall tour, or visit Mount Arvon, MI highest point! This is the place to relax & explore. Bicycles are available as well as kayaks! Comfortably sleep 2 in the queen bed. Full size futon & cot also. Things to do are endless!

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.

A Keweenaw Hidden Gem - 240 Acre Nature Retreat

If it’s nature and quiet you want to immerse yourself in, stay here to get away from the hustle, bustle and noise of life. Amongst the woods and pasture at the end of a road less traveled awaits your humble, cozy cabin. 3 miles of maintained private trails, 2 ponds, woods, a .75 mile walk to a lovely spot on Lake Superior or a 5 mile drive to public sandy swimming beach, boat launch, and lighthouse. Launch your Keweenaw adventures from this simple yet well-appointed tucked away hidden gem!

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. Handicap accessible with stairlift from garage. Full sized bed with additional pullout couch.

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.