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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Top guest favorite
An open living space features a vaulted ceiling with exposed beams. A rectangular dining table sits nearby, accompanied by colorful chairs. A black sofa is positioned next to large windows that offer views of the surrounding woods. A red refrigerator and a staircase to the loft are also visible.
Cabin in Greenland
4.95 out of 5 average rating, 44 reviews

Historic copper mine site - Entire Cabin

Private cabin at the historic Adventure Mine site. Amazing setting overlooking wooded valley. High speed internet suitable for video conferencing. Queen bed in loft, outdoor deck, full bath with shower. The Adventure Mine is a cooperating site of the Keweenaw National Historical Park. Underground mine tours, hiking trails, building ruins to explore! The loft is accessed by an offset-tread stairs. this may be difficult for those with limited mobility. We do not permit mineral collecting on site.

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, 123 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
4.83 out of 5 average rating, 113 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
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, 42 reviews

Black Barn Lodge

Newer build 2023, Starlink internet, Bill Nichols trail is 700 ft away Great location close to party stores and restaurants, Boiler in floor heat and hot water 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/ dock sxs, sleds,boats and bikes! Read the house rules on pet fees Owner may be on site at new barn

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, 142 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 favorite
Cabin in Bruce Crossing
5 out of 5 average rating, 9 reviews

Off-Grid Cabin in Michigan (UP)

Come Stay Off-Grid in Michigan's Beautiful Upper Peninsula The peaceful log cabin and surrounding 36 private acres of land are in the prime location for hunting, fishing, snowmobiling, ATVing, snowshoeing, hiking, fishing, bird watching, and more! It is fully off-grid, with propane heating and solar electricity. It also has a deep water well, and indoor plumbing - including a hot shower - to provide all the modern comforts you appreciate while still being in a secluded natural environment.

Top guest favorite
A spacious single-story lodge is depicted, featuring a green and white exterior. The well-maintained gravel driveway curves in front of the entrance, surrounded by a grassy area and trees. Expansive skies with clouds create a tranquil atmosphere.
Home in Mass City
4.91 out of 5 average rating, 68 reviews

Starry Sky Lodge on peaceful 38 acres-whole house

ATTN: Snowmobilers/UTV..Looking for activities? Come for a peaceful stay at Starry Sky Lodge. Snowmobiles and UTV get away as you are about 2 miles from trail 3. Or check out the mines and waterfalls. Visit the Porcupine Mountains for hiking and breathtaking views. Hike the trails in the state parks. If you need some city vibes-Houghton is nearby. And, of course, be sure to take in the night sky-away from the city lights! Whatever your interest is, we hope you will find it!

Superhost
Cabin in Toivola
4.94 out of 5 average rating, 18 reviews

Boonie No. 2

Cabin 2 boasts a prime location, right on Trail 3, with a beautiful golf course view. This cabin has 2 bedrooms; each with (1) full and (1) twin bed, large bathroom that is handicap accessible, ramp to the front door, wifi, & kitchen featuring microwave, coffee maker, refrigerator, stove and oven. Coffee & coffee filters are included with coffee machine. The beds have fresh linens and one extra blanket per bed. Towels are provided. Plenty of room for truck & trailer parking.

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, 125 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!

Superhost
The Yooper Lodge is surrounded by greenery, featuring a rustic farmhouse structure with a partially visible outdoor area. A camper is parked nearby, alongside an awning and several off-road vehicles. Towering trees provide shade to the spacious lawn.
Home in Toivola
4.82 out of 5 average rating, 44 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.

Top guest favorite
Cabin in Pelkie
4.98 out of 5 average rating, 160 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

Top guest favorite
The exterior of a cozy log cabin is surrounded by lush greenery. The cabin features a covered porch with wooden supports and multiple windows that provide a view of the forest. A gravel driveway leads up to the entrance, enhancing the serene natural setting.
Guesthouse in L'Anse
4.96 out of 5 average rating, 261 reviews

Silver River Cozy Cabin

Take it easy at this unique and tranquil getaway on the Silver River. A cozy log cabin beautifully hand crafted by the owner himself. There is one queen size bed along with a futon that folds out into a twin bed and a convertible couch which also folds down into a twin bed. Enjoy snowmobiling, snowshoeing, skiing, 4 wheeling, hiking, kayaking, boating, fishing, hunting and much more!

Popular amenities for Winona vacation rentals

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