Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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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
4.78 out of 5 average rating, 129 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. 8 beds 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

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
4.84 out of 5 average rating, 106 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, 134 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 cozy sleeping area features a quilt-covered bed, complemented by a sofa along one wall. Natural light fills the room through two windows, framed by light curtains. A rug adds warmth to the space, with a plant providing a touch of greenery.
Guest suite in Calumet Township
4.84 out of 5 average rating, 203 reviews

Guest Getaway Loft

Take a refreshing respite in the quiet or experience the bustle of historic downtown Calumet from our 500 sqft guest apartment. This studio apartment is lofted above the detached garage with a private entrance. Within walking distance of bars, restaurants, coffeehouses, bakeries, and local ski and snowmobile trails our guest home is a perfect place to explore all the Keweenaw peninsula has to offer. Guests have 24/7 access to the host, when necessary, as I live in the detached main house.

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
4.87 out of 5 average rating, 246 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 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, 184 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, 123 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.

Top guest favorite
A cozy sleeping area features a queen bed dressed in crisp white bedding. Two windows allow natural light to brighten the room, while a patterned armchair and a small black bench add comfortable seating options.
Guesthouse in Chassell
4.95 out of 5 average rating, 145 reviews

Cozy & Clean Chassell Roadside Cottage

This is a non-smoking studio type cottage with a queen bed and futon. The kitchen has a full-size refrigerator, sink, double burner hotplate, microwave, coffee maker, and toaster. Kitchen essentials are provided. Bathroom towels and bedding are also provided. Cottage also has a grill, air conditioning, Wi-Fi, and Netflix. (SORRY, NO PETS. NO SMOKING, OR PARTIES ALLOWED. $400 fine) Chassell beach is two blocks away, and hiking trails are 1 block. MTU is a 10 minute drive.

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, 115 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
4.99 out of 5 average rating, 269 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.

Top guest favorite
Cabin in Pelkie
4.98 out of 5 average rating, 145 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