Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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Top guest favorite

A modern black structure features a spacious driveway and a small gravel area. Four patio chairs surround a fire pit on a concrete slab. Large windows offer views into the interior. Lush greenery from surrounding trees enhances the natural setting.

Home in Elm River Township

5 out of 5 average rating, 35 reviews

Black Barn Lodge

New build 2023 4 season paradise Direct TV Starlink internet Bill Nichols trail is directly across the highway Great location close to party stores and restaurants Boiler hot water and heat 1st bedroom has a queen bed and blow up mattress Bedroom 2 comes with 2 queen beds Laundry room with 8 heavy duty gear hooks for your riding gear. Located on Little Gerald lake. Great fishing / access to two other lakes Private beach with dock sxs, sleds,boats and bikes! Read the house rules on pet fees

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, 230 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, 522 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.

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, 238 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, 218 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!

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, 115 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.

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, 122 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 vibrant landscape is filled with a mix of orange, red, and green foliage, creating a striking view of autumn colors. A winding river cuts through the forest, adding a sense of movement to the tranquil scene.

Home in Toivola

4.83 out of 5 average rating, 41 reviews

The Yooper Lodge! On the trail and close to lakes.

The Lodge is a great place to start your next adventure! It is centrally located to all the sights that the Western U.P. has to offer. Our place is a great base camp. The best trails and deep snow are as close as the front yard. Not to mention, trail #3 Bill Nicholls (one of the best in Michigan) is right across the road! Makes for great ATV and Snowmobile trips in all directions. There are restaurants, bars, and 2 gas stations/minimarts close by also.

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, 112 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 charming cabin is nestled among greenery, featuring a spacious deck that extends to the edge of a tranquil yard. The structure showcases a sloped roof and large windows, allowing for natural light to enhance the interior. Lake Superior can be seen in the background.

Cabin in Pelkie

4.98 out of 5 average rating, 138 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