Holiday houses in Winona

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Top-rated holiday rentals in Winona

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Top Guest favourite
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, 120 reviews

Quiet retreat on 18.5 acres for viewing wildlife.

Pricing is per bedroom; $144/night for 1 bedroom accommodating 1-2 guests. Additional $87/night for a second bedroom for 3-4 guests. A Tax of approximately 6% is added to this pricing. 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.

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
4.85 out of 5 average rating, 112 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 favourite
The rocky shoreline of Lake Superior is visible, featuring clear water gently lapping at the edge. Lush greenery and trees line the background, while the Copper Suite is partially visible, nestled among the natural landscape.
Home in Eagle Harbor
4.94 out of 5 average rating, 166 reviews

Cat Harbor - Copper Suite - On Lake Superior

Set on the shores of Lake Superior, the Copper Suite is one of two private units in the home, offering stunning, panoramic lake views. Step right outside to access cross-country ski and hiking trails. Enjoy a fully equipped kitchen, cozy indoor fireplace, lakeside back porch, heated garage, and outdoor wood-fired sauna. Whether you’re here to unwind, recharge or head out on adventures, it’s the perfect base for exploring the Keweenaw. Located near Copper Harbor, Eagle Harbor, and Mt. Bohemia.

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, 152 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 favourite
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, 539 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!

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, 137 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
Home in Ontonagon
4.9 out of 5 average rating, 180 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
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, 140 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.

Top Guest favourite
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, 140 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 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, 265 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, 209 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 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, 104 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.

Popular amenities for Winona holiday rentals

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