Holiday houses 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.

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. 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.

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.

Granny’s Place @northernbarn 1 Mile to Lake Sup

Animal Lovers, this studio is a quiet place to relax, 9miles (13 minutes) from town, after a day of outdoor activities. The space is a charming and quant, tiny 300 sq ft attached space, and offers a full bathroom, a full size bed, and efficiency kitchen with a microwave, hot plate and toaster oven (no stove or oven). This quiet space is located on a small hobby farm with a many social animals. Sip your coffee and watch our sheep graze before you head out on your next adventure

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.

2 story apartment - country feel, city convenience

Newly remodeled, two-story attached apartment with private entrance and ~1,000 sq ft of space. Sauna. Two Queen beds with top quality mattresses and bedding. Plenty of parking. Cap at 4 adults, but beds for kids available on request. Walking: 5 min to Tech Trails, 15 min to MTU/downtown. Internet TV only. Overall, it's very quiet, but we have two young children, and you will likely hear them between 7 am and 8 pm. Feel free to ask questions or make requests!

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