Holiday houses 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
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, 43 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 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, 122 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
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, 155 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 cozy cabin stands amidst a snow-covered landscape, featuring a wooden exterior and a sloped roof. Double glass doors create an entrance adorned with the cabin number. Nearby, a snow shovel and a container provide practical touches against the winter backdrop.
Cabin in Toivola
4.94 out of 5 average rating, 16 reviews

Boonie Cabin 5

This cabin is in a great location, with only a short walk (or ride) to the bar & restaurant. Cabin 5 is less than 2 years old with new furniture and great views year round. The cabin features a bedroom with a queen bed, full bathroom with a shower, and a full size pullout couch with air mattress. Kitchenette area has refridgerator, microwave and coffee machine. Coffee & coffee filters included. Plenty of truck and trailer parking. Immediate trail access. Fuel stations less than a mile away.

Guest favourite
A modern kitchen features sleek black cabinetry and open shelving displaying dishware and utensils. A wooden dining table with metal chairs is positioned centrally, complemented by stainless steel appliances and a contemporary range hood. Warm lighting enhances the inviting atmosphere.
Home in Hancock
4.95 out of 5 average rating, 209 reviews

Rustic, yet Modern Trailside Cottage/MTU 2.3 Miles

Experience the Copper Country's natural beauty from our flagship property! The Miner was tastefully decorated & pays tribute to the area’s rich copper mining history. It is quaint & relaxing, yet spacious enough for entertaining. The Miner is the perfect destination for couples, business travelers and small families as it sits at the gateway to the Keweenaw and is located steps from the famed Jack Stevens snowmobile trail. A portion of all bookings will donated to local youth hockey.

Guest favourite
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
4.86 out of 5 average rating, 253 reviews

SH Lake Escape w/Kayaks, Firepit, Fishing

Sandy Hollow is a 2-BR lakefront on Sandy Lake, in a peaceful cove just off the main lake. Perfect for families or couples, it offers sunsets, swimming, and four-season adventure right outside your door. Amenities 2 BR/4 beds Fire pit Grill & outdoor dining Pet friendly w/ dog lead Full kitchen, dishwasher, Keurig Wi-Fi & streaming TV Washer/dryer 3 kayaks, paddleboat Ride to snowmobile & ATV trails Enjoy fishing, kayaking, and sunset views—true lake life in the Western UP.

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 out of 5 average rating, 42 reviews

Black Barn Lodge

New build 2023 4 season paradise 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

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, 111 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.

Top Guest favourite
The exterior of the Fog Signal House is presented, featuring a gabled roof and light-colored walls. A pathway of flat stones leads to the entrance, bordered by lush green grass. The nearby shoreline of Lake Superior is visible, along with a clear blue sky.
Home in Allouez
4.96 out of 5 average rating, 26 reviews

Fog Signal House at Sand Hills

Enjoy an extraordinary couple's retreat at the historic Fog Signal House at Sand Hills Lighthouse. Originally built in 1919 to house two massive fog horns, the Fog House has been transformed into a relaxing space for two. Roam on 3000 ft of private Lake Superior shoreline, wake to stunning sunrises, stargaze at a pristine night sky. Tune into the remarkable landscape in any season. The design hearkens to its industrial past, but is full of contemporary amenities for your comfort.

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
4.91 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!

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.

Popular amenities for Winona holiday rentals

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