Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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Top guest favorite
A two-story cabin, set within a wooded area, features a welcoming front entrance with a white door framed by green accents. Flower pots hang on either side. A path leads to the entrance, surrounded by lush trees and a gravel driveway.
Cabin in Hancock
4.95 out of 5 average rating, 152 reviews

"Northbound" Secluded Cabin in Keweenaw Penninsula

Your Keweenaw adventure begins here! This centrally located cabin seated on a private 6-acre lot provides easy access to local favorites such as Copper Harbor, Mt Bohemia, Mt Ripley, Lake Superior, 1.5mi from UP17, and 3mi from UP13 ATV/snowmobile and bike trails. Close to many public boat ramps.Equipped with a full kitchen and living room, this cabin sleeps up to six people with a full bath. Ample parking for ATV/snowmobile trailers. The cabin is a short drive to Calumet, Hancock, and Houghton.

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, 149 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
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, 139 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
The cabin's exterior is illuminated at night, highlighting the intricate wooden structure and expansive glass windows. A wooden walkway leads to the entrance, surrounded by lush trees, creating a serene and inviting atmosphere.
Cabin in Allouez Township
4.95 out of 5 average rating, 160 reviews

Serenity on Superior

Relax with the whole family at this peaceful cabin on Lake Superior. The views are amazing day and night. With panoramic views from inside and out you’ll have amazing sunsets and spectacular views of the lake. The nighttime views of the stars and the Northern Lights are even better! Inside there is plenty of room to stretch out and relax, sit in front of the fireplace, relax in the jacuzzi tub or even play a game of pool. Just a short drive to Eagle River, Eagle Harbor and Copper Harbor.

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, 139 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
Apartment in Chassell
4.97 out of 5 average rating, 203 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 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, 102 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 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, 134 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
4.92 out of 5 average rating, 120 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
A dining area features a wooden table with four high stools beneath a classic chandelier. The black and white checkerboard flooring contrasts with the warm wooden walls and inviting decor, while a potted orchid adds a touch of greenery to the space.
Home in Houghton
4.92 out of 5 average rating, 221 reviews

Mantykoti "Pine house" in the heart of Houghton

LOCATION, history, world class trail access, & a unique, colorful, inviting, and fun home make this a must stay. Mantykoti, (Pine house- in Finnish), is one of the ONLY homes in central Houghton! This early 1900 historic beauty was restored and created with travelers in mind to enjoy a pristine rental while experiencing the Keweenaw to the fullest w/ fam/friends. We have worked hard to keep the historic beauty while renovating with modern/rustic touches.

Top guest favorite
The exterior of a cozy log cabin is surrounded by lush greenery. The cabin features a covered porch with wooden supports and multiple windows that provide a view of the forest. A gravel driveway leads up to the entrance, enhancing the serene natural setting.
Guesthouse in L'Anse
4.96 out of 5 average rating, 244 reviews

Silver River Cozy Cabin

Take it easy at this unique and tranquil getaway on the Silver River. A cozy log cabin beautifully hand crafted by the owner himself. There is one queen size bed along with a futon that folds out into a twin bed and a convertible couch which also folds down into a twin bed. Enjoy snowmobiling, snowshoeing, skiing, 4 wheeling, hiking, kayaking, boating, fishing, hunting and much more!

Popular amenities for Winona vacation rentals

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