Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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

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Guest favorite
A rustic cabin is nestled among tall trees, featuring a welcoming front porch with steps leading to a spacious deck. Large windows allow natural light to flood the interior, blending the home with its serene forest surroundings.
Cabin in Ontonagon
4.81 out of 5 average rating, 338 reviews

Driftwood Shores Cottage

Completely Furnished wifi/DVD Gas Fireplace Ski Storage Refrigerator/Microwave/Electric grill All linens Included Escape from the fast paced, hectic world and discover the quiet, serene wilderness of the Porcupine Mountains The best of Michigan's Lake Superior North Country Swimming out back on private beach Skiing & Snowmobiling Boating & Canoeing Camping & Hiking 100 Majestic Waterfalls Lighthouses-Old Restaurants Historical Museums Tunnel of Trees Ski area with 14 runs Call for more infou

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, 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
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 favorite
The exterior of the house features a well-maintained entrance with a front door and large window reflecting a sunset over the bay. Lush green grass and a small flower bed accentuate the inviting façade.
Home in L'Anse
4.98 out of 5 average rating, 123 reviews

Martha’s Bay View

Forget your worries in this spacious and serene space. We purchased this house from our dear grandmother who loved her view of the bay, hence the name; Martha’s Bay View. You cannot beat the beautiful view of Lake Superior and the amazing sunsets. Not far from 2nd Sand Beach for swimming and picnics. Use this as home base for all the sightseeing our area has to offer. Fully operational kitchen with microwave, coffee pot/Keurig. No pets and no smoking. All bedrooms and bathroom on second floor.

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, 154 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 tiny cabin is presented with a rustic wooden exterior and a green metal roof. Wood railings frame the entrance, leading to a spacious wooden deck with two chairs positioned for outdoor seating. A large star decorates the front wall, complemented by greenery surrounding the property.
Tiny home in Chassell
4.94 out of 5 average rating, 129 reviews

Tiny Home Glamping in the Keweenaw - 12 min to MTU

High-end glamping in the Keweenaw Peninsula. This tiny house/cabin features two lofts with queen-sized beds, a wood burning fireplace, dock with paddle boat on two acre pond, access to the Pike River and 20 acres of land for hiking and recreation. Cook in the kitchen or over the outdoor fire pit. Enjoy a wood-fired sauna and cool off with a dip in the pond. Bring a fishing rod and catch dinner out of the pond or the river! No running water but indoor composting toilet and a rain barrel/sink.

Guest favorite
Home in Ontonagon
4.9 out of 5 average rating, 182 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 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, 141 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
Home in Baraga
4.88 out of 5 average rating, 272 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
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, 123 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!

Top guest favorite
Apartment in Dollar Bay
4.99 out of 5 average rating, 299 reviews

"Copper Trails" Lovely Private Rental Unit

Easy access one bedroom unit in Dollar Bay. Right on the snowmobile trail, and convenient for all of the Copper Country’s activities: snowmobiling, skiing, biking, touring historical sites, Michigan Tech, etc. Entire upstairs of a detached garage. Private entrance. Well insulated for sound and comfort. Only 3 1/2 miles to Houghton/Hancock, and close to the airport. Trailer parking available. Crib and high chair available upon request.

Top guest favorite
A logo design features a kayaker paddling against a backdrop of a large orange sun. Tall green trees and a white bird are depicted to the side, highlighting themes of nature and outdoor activities. The text 'Kayak Shack Vacation Cottage' is prominently displayed beneath the imagery.
Cottage in L'Anse
4.93 out of 5 average rating, 215 reviews

Kayak Shack Vacation Cottage

Looking for a cottage to rent in Michigan's Upper Peninsula to enjoy a variety of Spring, Summer, Fall, and Winter activities. Look no further. Welcome to "Keweenaw Bay" located on beautiful Lake Superior. My vacation Cottage named, ‘Kayak Shack Vacation Cottage' is located just 1 mile N of L'Anse, MI., offering breathtaking sunsets, tranquil star-gazing, serene wildlife and the bay's many moods for you to enjoy.

Popular amenities for Winona vacation rentals

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