Holiday rentals in Winona

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Top-rated holiday rentals in Winona

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

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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, 124 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.

Top guest favourite
Home in Toivola
5.0 out of 5 average rating, 11 reviews

Lake Front Lodge on Lake Roland | Twin Lakes

Enjoy the charm of the Lake Front Lodge, featuring a private beach on Lake Roland and beautiful wooded property. Nestled in Michigan’s Upper Peninsula Twin Lakes area, 20 miles from Houghton and MTU this home is the perfect getaway. Spend your days kayaking, boating, fishing, or soaking up the peaceful lakeside. ATV, snowmobile and nature trails located nearby. Walking distance to Krupp's convenience store, gas station, golf course and several restaurants! Twin Lakes has it all for seasonal fun!

Top guest favourite
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
5.0 out of 5 average rating, 43 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 favourite
The kitchen features wooden cabinetry, stainless steel appliances, and ample countertop space. A refrigerator, dishwasher, and an oven are visible. A blend of natural light and artificial lighting creates a welcoming environment. Bar stools provide seating at the counter.
Home in Bruce Crossing
4.84 out of 5 average rating, 148 reviews

Private 5 Star Home in B.C. w/Sauna + Parking

Newly remodeled house downtown Bruce Crossing. *Sleeps 8 *Walking distance to restaurants, bars and groceries. *Next to snowmobile trail. *Quiet location. *Lots of parking. *4-6 person sauna. *Showers upstairs and down. *Fully stocked kitchen: Cookware+utensils, dishes, silverware, glasses, measuring cups and spice rack. Appliances : coffee maker+coffee, fridge & freezer, oven, dishwasher, toaster, blender microwave & washer/dryer. *WiFi throughout house. *Pool table, dart board & game area.

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, 144 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 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, 279 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
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
4.94 out of 5 average rating, 135 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, 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 favourite
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
4.9 out of 5 average rating, 126 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 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
4.96 out of 5 average rating, 114 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. There is a parking pad for your RV or trailer. *Please note that the entry is on the basement level and the main living area is up a flight of stairs.

Top guest favourite
Cabin in Pelkie
4.98 out of 5 average rating, 161 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 favourite
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.
Guest house in L'Anse
4.96 out of 5 average rating, 264 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 holiday rentals

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