Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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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

4.87 out of 5 average rating, 103 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

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, 130 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 full-size Murphy bed is shown in the lowered position, with a light yellow bedspread and dark blue pillows. The wall behind features sleek white cabinets above the bed, while a bedside table is visible to the left.

Shipping container in Atlantic Mine

4.96 out of 5 average rating, 101 reviews

Shipping Container close to Houghton

Low monthly rate. Small and cozy 20ft shipping container w/ concrete patio 3 miles from Houghton. Outdoor sitting space. Plenty of parking. Small refrigerator freezer combo. Small oven fits 12-in pizza. Keurig coffee maker, K-Cups provided. 2 burner hot plate. 3/4 bathroom. Pull down FULL size (NOT Queen) Murphy bed with attached table when up. Pots, pans, silverware, dishes and cups provided. Good drinking water from faucet. Bed linens and towels provided. Wi-Fi and smart TV. NO TV carrier.

Superhost

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

4.77 out of 5 average rating, 127 reviews

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.

Top guest favorite

A cabin nestled on a rocky shoreline overlooks the waves of Lake Superior. Surrounding trees display vibrant autumn foliage, creating a natural contrast with the tranquil blue water. The cabin features a deck that extends towards the shoreline, providing a serene outdoor space.

Cabin in Eagle Harbor

4.99 out of 5 average rating, 122 reviews

True North Cabin on Lake Superior by Copper Harbor

True North Cabin on Lake Superior in Michigan's Keweenaw Peninsula is a two-acre private retreat. At the end of a small circle driveway nestled into the forest, you'll be welcomed by the sound of waves as you arrive at our renovated cabin. You'll have all the amenities for a memorable vacation stay. Explore the rocky conglomerate shore and be inspired by freighters, local wildlife, and starry skies with the perfect vantage point to see the northern lights. Social Media: True North Cabin

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, 114 reviews

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.

Guest favorite

A rustic canvas tent is set on a wooden platform surrounded by greenery. Two Adirondack chairs are positioned on the deck, with a small table nearby. Firewood is neatly stacked beside the tent entrance. Soft lighting enhances the inviting ambiance.

Tent in Houghton

4.95 out of 5 average rating, 158 reviews

Private Camp @northernbarn 1 Mile to Lake Superior

Adventurers, you won’t forget the peaceful surroundings of this off grid rustic, 3 season campsite in the woods. Camp is designed to help immerse you in nature, and is tucked deep within the woods. Warm up inside with a wood stove fire & brew coffee, roasted at the farm. Finish your day with a nice hot sauna. A little romantic spot for couples to slow down and reconnect with each other. Wifi is available by the house if needed. Camp has a tent outhouse with a portable toilet

Top guest favorite

A bright living space features large sliding glass doors that open to a scenic view outside. A round wooden dining table is accompanied by four chairs, while a comfortable couch and a small fireplace add to the inviting atmosphere. Natural light fills the room.

Apartment in Chassell

4.97 out of 5 average rating, 177 reviews

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.

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

4.93 out of 5 average rating, 121 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

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, 41 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 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, 111 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.

Top guest favorite

A compact kitchen area features modern appliances including a stove, refrigerator, and microwave. The black countertop contrasts with the orange cabinets below. Skylights provide natural light, while a trash bin and seating are positioned nearby, enhancing the functionality of the space.

Apartment in Dollar Bay

4.98 out of 5 average rating, 253 reviews

"Copper Trails" Lovely Private Rental Unit

Easy access one bedroom unit in Dollar Bay. Right on the snowmobile trail, and convenient for all of the Copper Country’s activities: snowmobiling, skiing, biking, touring historical sites, Michigan Tech, etc. Entire upstairs of a detached garage. Private entrance. Well insulated for sound and comfort. Only 3 1/2 miles to Houghton/Hancock, and close to the airport. Trailer parking available. Crib and high chair available upon request.