Holiday houses in Winona

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Top-rated holiday rentals in Winona

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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 favourite
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, 140 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 favourite
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 favourite
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
4.85 out of 5 average rating, 210 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.

Top Guest favourite
Home in Ontonagon
4.9 out of 5 average rating, 170 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!

Guest favourite
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 favourite
Apartment in Chassell
4.97 out of 5 average rating, 189 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 favourite
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, 126 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 favourite
A charming two-story duplex is displayed with a welcoming front porch. The light-colored exterior is complemented by large windows, allowing natural light to fill the interior. Lush greenery surrounds the property, enhancing the serene environment. A well-maintained pathway leads to the entrance.
Home in Hancock
4.87 out of 5 average rating, 117 reviews

Hancock Old Mining House (Duplex)

Upstairs half of duplex in Hancock. This mining era house was converted to a duplex somewhere along the way. The living space is completely private but there is a shared entrance with the lower unit on the front porch. Our co-host Shelby lives in the lower unit. This Airbnb listing not a luxury rental It's an old but clean, functional apartment that is ideal for one to two quiet guests. We purchased house in 2021 and lived in the lower unit until March of 2024.

Guest favourite
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.

Top Guest favourite
A compact kitchenette is equipped with white cabinetry and a grey countertop. Appliances include a microwave, electric cooktop, and mini fridge. A small sink is located under the cupboards. A stylish rug is placed on the floor in front, and natural light is visible through a nearby door.
Apartment in Hancock
4.94 out of 5 average rating, 144 reviews

*Studio 15* Studio Apartment in West Hancock

This studio space is all fresh and new, located in west Hancock. Parking is easily accessible with a ground floor entryway. Downtown Hancock and Houghton are just minutes away. Located near the Hancock beach. If you aren't a camper but enjoy the day activities come and stay with all the luxuries of home. Studio size kitchen and a king size bed. We just added a heater/ air conditioner that is adjustable by the guest. The feedback has been great!

Top Guest favourite
Cabin in Pelkie
4.98 out of 5 average rating, 150 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 holiday rentals

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