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

4.88 out of 5 average rating, 104 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.

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

4.85 out of 5 average rating, 229 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. Fire pit w/wood Grill & Outdoor dining Lead cable 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.

Guest favorite

A white cabin with a green roof is set against a clear blue sky, surrounded by lush greenery. A well-maintained path leads from the cabin towards the lake. The calm waters of Portage Lake reflect the serene landscape, providing a tranquil backdrop.

Home in Chassell

4.88 out of 5 average rating, 520 reviews

Rustic cabin w/sauna on Portage Lk

Located on Portage Lake in Chassell, MI, near Houghton with quick access to Michigan Tech University, this rustic family cabin is a great place for either an overnight stay or a longer getaway. It provides a great home base for travel in the Keweenaw peninsula! As a 1930s cabin with a sauna on the lake along with a great view, the focus is on the experience! We find guests who truly enjoy our place are flexible with rustic conditions (not looking for Holiday Inn Express) and young at heart!

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 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, 124 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

4.87 out of 5 average rating, 235 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.

Guest favorite

The cabin's exterior features a modern design with a dark color scheme and a sloped roof. A grill is positioned beside the entrance, while lush greenery surrounds the property, providing a natural setting. A gravel pathway leads up to the front door.

Cabin in Hancock

4.84 out of 5 average rating, 217 reviews

High Rock Cabin- 200 ft to trail 17! Close to town

Welcome to our “High Rock Cabin”. This centrally located tiny house is right by the trails. Set in the woods, but only a couple miles from Hancock/Houghton! One main floor bedroom with queen bed, and a loft with two full beds. Please be aware that there is a spiral staircase to access the loft. No smoking in cabin. Will be a $250 fee if smoking is detected. Also, pets must be approved by owners. Will entail an additional pet fee. There is plenty of parking, enough room for a trailer!

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.

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, 178 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.

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

A log cottage stands beside a grassy area, framed by colorful autumn foliage. A seating area with Adirondack chairs is visible near the shoreline, offering views of Lake Superior in the background. Natural stone accents complement the warm wood exterior of the cottage.

Vacation home in Ontonagon

4.97 out of 5 average rating, 129 reviews

Lake Superior Get-Away

This Lake Superior cottage is perfect for an up north get-away. Enjoy the breathtaking sunsets, strolls along the beach, swimming, kayaking or making your evenings memorable by sitting around the fire pit getting lost in the flames. This Northwoods style home is located 10 minutes from the spectacular Porcupine Mountains. 186' privately owned beach property. At 400 sq ft of living, it comfortably sleeps four with one bedroom and loft area. Two Kayaks are complimentary.

Guest favorite

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

4.86 out of 5 average rating, 103 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.