Vacation rentals in Winona

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Top-rated vacation rentals in Winona

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A rustic cabin is nestled among tall trees, featuring a welcoming front porch with steps leading to a spacious deck. Large windows allow natural light to flood the interior, blending the home with its serene forest surroundings.
Cabin in Ontonagon
4.81 out of 5 average rating, 346 reviews

Driftwood Shores Cottage

Completely Furnished wifi/DVD Gas Fireplace Ski Storage Refrigerator/Microwave/Electric grill All linens Included Escape from the fast paced, hectic world and discover the quiet, serene wilderness of the Porcupine Mountains The best of Michigan's Lake Superior North Country Swimming out back on private beach Skiing & Snowmobiling Boating & Canoeing Camping & Hiking 100 Majestic Waterfalls Lighthouses-Old Restaurants Historical Museums Tunnel of Trees Ski area with 14 runs Call for more infou

Top guest favorite
Home in Toivola
4.94 out of 5 average rating, 16 reviews

Lake Front Lodge on Lake Roland | Twin Lakes

Enjoy the charm of the Lake Front Lodge, featuring a private beach on Lake Roland and beautiful wooded property. Nestled in Michigan’s Upper Peninsula Twin Lakes area, 20 miles from Houghton and MTU this home is the perfect getaway. Spend your days kayaking, boating, fishing, or soaking up the peaceful lakeside. ATV, snowmobile and nature trails located nearby. Walking distance to Krupp's convenience store, gas station, golf course and several restaurants! Twin Lakes has it all for seasonal fun!

Top guest favorite
A snow-covered landscape is bathed in warm light from a setting sun. A large tree stands nearby, surrounded by mounds of snow. In the distance, the outline of a house can be seen, along with a vehicle parked on a snow-blanketed surface.
Home in Greenland
4.98 out of 5 average rating, 163 reviews

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.

Top guest favorite
A wooden pathway leads to a cozy log cabin nestled among vibrant autumn foliage. The cabin features a wraparound porch adorned with railing, showcasing large windows that reflect the blue sky above. Sunlight filters through the surrounding trees, creating a serene ambiance.
Cabin in Ontonagon
5.0 out of 5 average rating, 110 reviews

Driftwood Cabin

Slow down, unplug, and relax in a cozy North woods log cabin with a private beach on the sandy shore of Lake Superior. Start your day by enjoying a cup of coffee on the back deck watching the sunrise and end your day sipping a cocktail on the beach watching the sunset, stars, or Northern Lights. The Driftwood Cabin is located west of the quaint town of Ontonagon, close to the Porcupine Mountains Wilderness State Park. Recharge your imagination, play outdoors, and enjoy a memorable vacation!

Guest favorite
The exterior of Jake's Bed & Bar features a vibrant red facade, and a sign indicating the bar's name hangs prominently above the entrance. A welcoming path leads to the entrance, with a landscaped area of small plants and a calm husky dog resting nearby.
Home in Toivola
4.79 out of 5 average rating, 148 reviews

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.

Top guest favorite
A ranch-style house with a light-colored exterior is set against a backdrop of tall, bare trees. The structure features large windows and a deck with green chairs, creating an inviting outdoor space. A spacious yard in front adds to the tranquil atmosphere.
Home in Toivola
4.94 out of 5 average rating, 138 reviews

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, 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.

Guest favorite
A story and a half house is set within a lush green landscape, surrounded by trees and vibrant flowering shrubs. A pathway leads to the entrance, with a porch visible at the front. The sky is partly cloudy, adding a serene ambiance to the scene.
Home in Nisula
4.91 out of 5 average rating, 130 reviews

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!

Guest favorite
The Yooper Lodge is surrounded by greenery, featuring a rustic farmhouse structure with a partially visible outdoor area. A camper is parked nearby, alongside an awning and several off-road vehicles. Towering trees provide shade to the spacious lawn.
Home in Toivola
4.83 out of 5 average rating, 47 reviews

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.

Guest favorite
A covered porch features wooden flooring and is equipped with a set of chairs and a small table. Natural light illuminates the space, and surrounding greenery is visible through the railing, creating a calm outdoor retreat.
Cabin in Chassell
4.94 out of 5 average rating, 119 reviews

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. There is a parking pad for your RV or trailer. *Please note that the entry is on the basement level and the main living area is up a flight of stairs.

Top guest favorite
Cabin in Pelkie
4.98 out of 5 average rating, 164 reviews

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

Top guest favorite
A single-story home with a light-colored exterior and red roofing is set against a backdrop of greenery. The front yard features a grassy area, while a bluff rises in the distance. Nearby trees provide a natural setting, enhancing the outdoor atmosphere.
Home in Mass City
4.93 out of 5 average rating, 113 reviews

Bluff View Hideaway

Relax at this cozy small town home with the beautiful bluff in your backyard. Enjoy the great outdoors with recreational trail access and trailer parking available right on site. Walking distance to the local grocery store, bar/restaurant and gas station. The towns friendly atmosphere will have you eager to return for another stay.

Top guest favorite
A two-story house is shown with gray siding and large windows. Two entry doors are visible, one on the main level and another above, with weathered steps leading to both. Surrounding trees are present, and a bright blue sky creates a peaceful atmosphere.
Home in Greenland Township
4.95 out of 5 average rating, 132 reviews

UP Destination

Great family vacation get away, one bedroom on main floor, two bedrooms upstairs. Full kitchen and laundry access. Close to snowmobile and ATV/UTV trails, enjoy the relaxation of quiet outdoors with the remote location in the country. Less than an hour from Houghton, the Porcupine Mountains, and the Ottawa National Forest.

Popular amenities for Winona vacation rentals