Vacation rentals in Winona

Lakeside Loft, Roof Deck + Sauna

Wanderloft, designed by architect David Salmela, combines modern Scandinavian design with the natural beauty of Wisconsin's Northwoods. Located on one of Vilas County's highest points, this cabin provides stunning 360-degree views from various levels overlooking Manuel Lake and 9.4 acres of land. Beyond its striking design, Wanderloft is defined by its profound sense of peace and quiet - where natural beauty and thoughtful architecture create space for rest, creativity, inspiration, and renewal.

Rustic Farm House

Secluded small farm house nestled in among maple, apple and pine trees. Lots of parking for trailers and guests. Wood burning Sauna on property. Just a short walk down the hill is our Private rock beach On Lake Superior with a fire pit to get cozy and watch the sunset. The main cabin also has a fire pit for your enjoyment. This is a quiet place with whitetail deer being the only thing to come and visit. Occasionally you’ll see bald eagles fly overhead looking for their dinner. Walking trails.

Cat Harbor - Copper Suite - On Lake Superior

Set on the shores of Lake Superior, the Copper Suite is one of two private units in the home, offering stunning, panoramic lake views. Step right outside to access cross-country ski and hiking trails. Enjoy a fully equipped kitchen, cozy indoor fireplace, lakeside back porch, heated garage, and outdoor wood-fired sauna. Whether you’re here to unwind, recharge or head out on adventures, it’s the perfect base for exploring the Keweenaw. Located near Copper Harbor, Eagle Harbor, and Mt. Bohemia.

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.

Serene Lake Superior Cottage

Newly updated in 2018, Graystone Cottage is directly on Lake Superior with 100 feet of gray stone beach frontage. Enjoy your morning coffee on the spacious patio with panoramic views of the Huron Mountains and Little Traverse Bay. Maybe spot a Bald Eagle fishing or flying to its nearby nest. For those relaxing summer nights, sit on the large deck and watch the moon rise or roast marshmallows on a bonfire while you listen to the waves crashing. 2 kayaks and life jackets available for use.

Steve's Spot - a Porcupine Mt. Adventure Getaway

Perfect location! You'll have this newer home all to yourself on a quiet road, just 2 miles from Lake Superior, 10 miles to the Porcupine Mountains, and 5 miles to town for gas and groceries. ORV trails just down the road! You'll be more than comfortable in this up to date modern 3 bedroom home, with fully equipped kitchen, laundry on site, and 1 and a half sparkling clean bathrooms! Also includes a pool table, ping pong, and foosball. This is a vacation location you can't afford to miss!

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.

Serenity on Superior

Relax with the whole family at this peaceful cabin on Lake Superior. The views are amazing day and night. With panoramic views from inside and out you’ll have amazing sunsets and spectacular views of the lake. The nighttime views of the stars and the Northern Lights are even better! Inside there is plenty of room to stretch out and relax, sit in front of the fireplace, relax in the jacuzzi tub or even play a game of pool. Just a short drive to Eagle River, Eagle Harbor and Copper Harbor.

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.

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.

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. More snow is on the way!

The Trails and Adventures Are Calling!

Drive right on to the trail! Historic feeling mining company house in Painesdale! This place has a full kitchen with laundry closet, dining room, living room with wood piers, 3 bedrooms with queen beds, and a full bathroom! The driveway has parking for large vehicles/trailers. Just off M26, approximately 8 miles from the City of Houghton. The Bill Nichols Snowmobile/ATV trail is right across the street! This is the perfect place for your Copper Country/Keweenaw getaway!