Vacation rentals in Winona

4.92 out of 5 average rating, 25 reviews

A deck area features a propane grill alongside a table with four floral-patterned chairs. An umbrella provides shade. In the background, Lake Superior glistens under the sun, with grassy land leading to the water's edge and trees framing the scene.

Home in Lake Linden

The Captain, Dockside Resort, Mt Bohemia, Trails!

TroyRating, 5 stars2 months ago

Beautiful location and property. The house was clean and finished like a new home. Accommodations were excellent for our group of 6. Location and views were perfect, id love to visit in summer. Host was top notch on every level. Thank you.

4.91 out of 5 average rating, 107 reviews

The cottage exterior features a charming wood shingle facade, with a welcoming deck adorned with string lights. The entrance is framed by large glass doors, leading into the inviting interior, while potted plants add a touch of greenery on the deck.

Cottage in Calumet

on Lake Superior-Clubhouse Cottage-Cozy Hideaway

LindsayRating, 5 stars2 months ago

We stayed for a weekend ski trip to Mt Bohemia. It was a short (40 minute drive) which was perfect for decompressing after a long day on the hill. We loved the beautiful views of Lake Superior! The cottage was the perfect size for the two of us with all the kitchen amenities we needed to cook all our meals. It was warm, cozy, and very relaxing. Thank for a great stay!

4.99 out of 5 average rating, 118 reviews

A view from the enclosed sunroom showcases a sandy path leading to Lake Superior, framed by glass doors. Two colorful chairs sit on the beach, inviting relaxation. The tranquil water stretches to the horizon, with grassy patches visible on either side of the path.

Cottage in Lake Linden

Simply Superior Cottage

KellyRating, 5 stars6 months ago

Great location right on the water. We watched the sunrise right out of the horizon every morning. Was a great place to cook, watch movies, read, rest and relax but was also close enough to go out for a day of exploring in Copper Harbor (hour away). Going to Copper Harbor in fall was amazing & the colors were beautiful the entire drive. 🍁 There are neighbors but we had no issues. Beach was basically empty the whole time so very private. We did some morning (sunrise) & evening (moon) yoga by the beach. Rooms & beds were comfortable, overall great place & we would stay again. I would stay here again.

4.95 out of 5 average rating, 247 reviews

An outdoor hot tub is positioned on a wooden deck, surrounded by tall trees. Large windows of the chalet illuminate the space with natural light, providing a glimpse of the inviting interior. The entrance door is visible, offering easy access to the hot tub area.

Chalet in Bessemer

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

KaitlinRating, 5 stars4 weeks ago

Great chalet! It was clean and well we're greeted with a dog basket with all the essentials (that was super helpful and amazing). The hot tub was lovely, warm, and CLEAN. All of the beds had different firmness and softness so it can accommodate many different preferences. The dishes were clean, which always makes me happy. We had a lovely stay and would definitely recommend this rental to others.

4.94 out of 5 average rating, 211 reviews

A serene view of Lake Superior showcases clear blue water that gently laps against a sandy shore. The horizon is visible in the distance, blending with a clear sky, offering a peaceful setting ideal for relaxation and connection with nature.

Home in Ontonagon

DJ's Destination U.P. (809) - 4 Bedroom & Two Bath

BrianRating, 5 stars1 month ago

From the minute I booked, Justin was on it. I’m sure Dawn is just as kind. Exactly what we were looking for at a nice price. Clean and convenient. Trail was a block away, we rode. Thanks Justin and Dawn! We had a great stay.

4.91 out of 5 average rating, 188 reviews

The entrance of the cottage features a wooden deck with a railing, adorned with two green chairs. Above the door, black and white photographs are displayed. The front door is painted a calming teal, complementing the light blue exterior of the cottage.

Cottage in L'Anse

Kayak Shack Vacation Cottage

LeanaRating, 5 stars2 months ago

It was my first time in the UP for the winter! Dave’s place was the perfect spot for our day trips around the Keweenaw peninsula. On our way to L’Anse it started snowing and Dave checked to make sure we made it and to let us know they were going to plow the driveway in the morning. We would definitely stay there again.

4.96 out of 5 average rating, 136 reviews

Home in Hancock

Lakefront home, Hot tub, near McLain State Park

AprilRating, 5 stars2 weeks ago

It’s all about the view at this home! Everything is as described with an added bonus that the lake is even closer than it appears in the pictures. Close enough to be in Houghton in minutes via a beautiful drive but far enough away to be secluded and peaceful. Plenty of space for our small family, but if you max out with 8 people it may be tight as the bathrooms are a bit smaller.

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Popular amenities for Winona vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Winona

5 out of 5 average rating, 9 reviews

A spacious jetted tub occupies the center of a wooden-paneled room, surrounded by subtle lighting. A cozy corner features a decorative tree adorned with colorful lights, and a mural depicting nature adds a serene backdrop. A bench is present, providing additional seating.

Home in Bessemer

Oui Ski Inn: Snowy Summit

NinaRating, 5 stars1 month ago

We loved our stay here! Just a quick walk over to the base of Big Powderhorn, and very comfortable.

4.95 out of 5 average rating, 37 reviews

A newly constructed home is viewed from across the water, featuring a dark exterior with white trim. Large windows and a spacious porch underline its design, which is surrounded by trees that exhibit early spring foliage. The house is positioned along a sandy shore.

Home in Ontonagon

Lakeside Lookout 3 Bedroom Home

AndyRating, 5 stars2 months ago

Great place for a snowmobile trip! Trail is only 1.5 miles down the road. The view of superior was fantastic and the house was a comfortable place to hang out when we weren't riding.

4.96 out of 5 average rating, 112 reviews

A three-story cabin is nestled within a snowy landscape, surrounded by tall trees. Its peaked roof and large balconies offer charming outdoor spaces. A gentle slope is noted in the foreground, blanketed in fresh snow, with the cabin appearing inviting and secluded.

Chalet in Bessemer

Big Chalet with Hot Tub on Big Powderhorn Mountain

AshleyRating, 5 stars4 weeks ago

We thoroughly enjoyed our stay at the Snow Escape! Beautiful home in a lovely location and the amenities (hot tub, sauna, etc) are top notch. I can’t recommend this place enough and I absolutely would love to return!

4.77 out of 5 average rating, 71 reviews

Cabin in Lac du Flambeau

Thunderbird Lodge: Spring/Summer Specials! Pets Ok

T-ShawnRating, 5 stars4 months ago

Well decorated cabin and good sceneries around!

4.99 out of 5 average rating, 77 reviews

A private dock extends into Portage Lake, surrounded by lush green grass and trees. The sunlight reflects off the water, creating a shimmering effect. The serene landscape offers a peaceful atmosphere, ideal for relaxation by the lake.

Cottage in Lake Linden

Camp Bootjack

MaryRating, 5 stars6 months ago

Absolutely gorgeous setting right on the lake. The home was comfortable, welcoming, and had everything we would need. We will certainly stay here again.

5 out of 5 average rating, 17 reviews

A snow-covered outdoor area is visible, showcasing a spacious patio with a hot tub and a Blackstone grill under a wooden overhang. Surrounding trees are draped in fresh snow, creating a serene and tranquil environment.

Villa in Iron River

UP north getaway with Hottub!

MicahRating, 5 stars1 month ago

Shelly was super responsive and overall an amazing hostess. She helped us with any questions we had before the trip and the couple we had during. She always responded within 30 mins of us reaching out :) The cabin was exactly as described in the listing and had everything we needed! Plus it was right around the corner from Ski Brule so we never had to travel to ski. Would highly recommend staying here- we will be coming back!

Villa in Bessemer Township

A comfortable living area features a rustic wooden wall, a brick fireplace, and large windows draped with dark curtains. A coffee table sits in the center, accompanied by a cozy armchair and a sofa, creating an inviting space for relaxation.

5 out of 5 average rating, 5 reviews

Cozy Ski Lodge Condo I Alpen Villas at Powderhorn

SamanthaRating, 5 stars1 month ago

We absolutely loved our stay! The connivence of the ski in and ski out was amazing. The rooms were a good size. Pillows comfy. We had three children with us that loved the bunk bed bedroom. The hot tub was clean and a perfect way to end the night after skiing. There is a puzzle and an arcade machine available for family fun. We would have loved to see a deck of cards or board game; but generally speaking those are items that can be brought from home. Overall, the cabin was perfect..