Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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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
4.84 out of 5 average rating, 107 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 serene lakeside scene features a dock and a small rowboat on the water. Red outdoor chairs are arranged in a circle on a grassy area, surrounded by trees. A dog rests comfortably nearby, enjoying the tranquil environment.
Home in Toivola
4.86 out of 5 average rating, 240 reviews

SH Lake Escape w/Kayaks, Canoe, Firepit, Fishing

Escape to Sunsets, swimming, kayaks, snowmobile & ATV trails. Our charming 2 bedroom house situated on Sandy Lake frontage, nestled in a serene cove just off the main lake. 4 beds Fire pit w/wood Grill & Outdoor dining Lead for dogs WiFi w/Streaming Full kitchen w/ dishwasher & keurig Washer/dryer 2 Fullsize Kayaks, 1 childrens kayak, Paddleboat, and Rowboat All the true amenities of a perfect vacation! We offer varied pricing by day/season making it easy for you to plan your perfect vacation.

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, 138 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 modern, single-story structure is set within a lush green lawn, framed by tall trees. Outdoor seating is provided on a patio, accompanied by kayaks and a small storage shed nearby. Large glass doors allow natural light to fill the interior.
Cottage in L'Anse
4.96 out of 5 average rating, 136 reviews

Perfect Couple's Get-Away with Private Beachfront!

Rock Beach-182’ of Lake Superior shoreline is your beachfront get-away! Search for agates, pick beach glass, kayak, fish, cycle along the shore, explore waterfalls, back roads, and sandy beaches! Participate in many local events-summer concerts, fishing tournaments, waterfall tour, or visit Mount Arvon, MI highest point! This is the place to relax & explore. Bicycles are available as well as kayaks! Comfortably sleep 2 in the queen bed. Full size futon & cot also. Things to do are endless!

Guest favorite
A charming cabin with gray siding is nestled among snow-covered trees, illuminated by a warm light from the front door. A shoveling shovel is positioned by the entrance, and the surrounding area is blanketed in fresh snow, creating a serene winter atmosphere.
Cabin in Ironwood
4.96 out of 5 average rating, 559 reviews

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for hiking, biking, fishing, boating and everything in between. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

Guest favorite
A cozy living room is revealed, featuring a large window that allows natural light to enter. Comfortable armchairs and a modern coffee table are arranged around a stylish area rug. A decorative fireplace is displayed, complemented by a vibrant television mounted on the wall.
Home in Ontonagon
4.9 out of 5 average rating, 169 reviews

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!

Top guest favorite
A serene landscape showcases a calm pond reflecting the evening sky, surrounded by lush greenery. The cozy cabin features large windows allowing natural light to fill the interior, with a spacious bed visible in a warmly decorated room. An inviting exterior is seen with a metal roof.
Cottage in Lake Linden
4.98 out of 5 average rating, 209 reviews

A Keweenaw Hidden Gem - 240 Acre Nature Retreat

If it’s nature and quiet you want to immerse yourself in, stay here to get away from the hustle, bustle and noise of life. Amongst the woods and pasture at the end of a road less traveled awaits your humble, cozy cabin. 3 miles of maintained private trails, 2 ponds, woods, a .75 mile walk to a lovely spot on Lake Superior or a 5 mile drive to public sandy swimming beach, boat launch, and lighthouse. Launch your Keweenaw adventures from this simple yet well-appointed tucked away hidden gem!

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, 135 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

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, 251 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
Apartment in Chassell
4.97 out of 5 average rating, 188 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. Stairlift from garage. Queen sized bed with additional pullout couch (about full sz) and toddler bed.

Top guest favorite
A ranch-style house is situated amid a snowy landscape, featuring a large front deck. The surrounding area is blanketed in snow, with a clear blue sky and scattered clouds above. Trees line the background, providing a sense of openness and tranquility.
Home in Toivola
4.94 out of 5 average rating, 125 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, 116 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.

Popular amenities for Winona vacation rentals

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