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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Top guest favorite
A cottage sits surrounded by greenery, featuring a two-story design with large windows and a welcoming porch. Comfortable outdoor seating is positioned on the deck, which offers views of the expansive lawn and distant trees. A white fence lines the property, adding to the serene atmosphere.
Cottage in Pelkie
4.96 out of 5 average rating, 120 reviews

Quiet retreat on 18.5 acres for viewing wildlife.

Pricing is per bedroom; $144/night for 1 bedroom accommodating 1-2 guests. Additional $87/night for a second bedroom for 3-4 guests. A Tax of approximately 6% is added to this pricing. 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.

Superhost
The exterior of the property is surrounded by tall trees, providing a natural frame. The single-story house features a red and light-colored facade with a garage in view. A spacious yard is evident, leading to serene greenery in the background.
Home in Toivola
4.85 out of 5 average rating, 112 reviews

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.

Top guest favorite
Home in Houghton
4.98 out of 5 average rating, 103 reviews

Guesthouse w/Heated garage/Fib intern/EV near MTU

Welcome to our 2023-built guest house, designed for your comfort. Enjoy in-floor heating, top-of-the-line appliances, full kitchen, garage. Relax on the patio with a gas grill. Stay connected with high-speed fiber optic internet, perfect for streaming or working. Just 5 minutes from MTU, Downtown, the Portage Canal, ski and bike trails. A golf course is close by, and grocery stores are a 7 min - drive away. Nestled in a serene neighborhood with pine and birch trees, enjoy nature's tranquility.

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, 153 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
Home in Dollar Bay
5 out of 5 average rating, 120 reviews

Relaxing Lakeside Home 5 Brdm 7 Beds *HOT TUB*

Our peaceful 5-bedroom lakefront home is 4 miles from Houghton and is conveniently located near the airport, Michigan Tech, Mont Ripley (3 miles) and Mount Bohemia (38 miles). Snowmobile trails are only 1/3rd of a mile away and you can ride your sled from here. Enjoy spectacular views of the lake, kayaking, and campfires on the patio. Our area is full of history and charm. Come visit! Parking for 3 trucks, plus trailers. Please Note: We charge $10 per night per person over 2 people.

Guest favorite
Home in Toivola
4.78 out of 5 average rating, 141 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.

Guest favorite
A charming blue house is featured, with a welcoming front entrance and large windows. An American flag is displayed prominently on the porch. The surrounding lawn is well-kept, and a gravel path leads to the entrance.
Home in Baraga
4.88 out of 5 average rating, 271 reviews

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.

Top 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
4.95 out of 5 average rating, 107 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. 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.

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, 135 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 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.

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, 123 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!

Superhost
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
4.82 out of 5 average rating, 44 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.

Top guest favorite
Cabin in Pelkie
4.98 out of 5 average rating, 155 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

Popular amenities for Winona vacation rentals

  1. Airbnb
  2. United States
  3. Michigan
  4. Houghton County
  5. Winona