Apartment holiday rentals in Winona

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Top-rated apartment rentals in Winona

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

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Top guest favourite
A garden-level apartment is accessed via a gravel driveway that leads to a charming home. Lush greenery surrounds the path, and the structure features a mix of siding colors, with large windows framed by blue shutters, creating an inviting exterior appearance.
Flat in Rochester
4.93 out of 5 average rating, 203 reviews

Woodland Retreat, Full private walkout lower level

Peaceful retreat down gravel driveway 15 min from Mayo Clinic. Enjoy your own apartment with private backyard walkout entrance to the lower level of our home. You will have a bedroom, living area, kitchenette with mini fridge, microwave and toaster oven (no conventional stove/oven), bathroom w/ tub & shower, pingpong table, laundry, and patio with fire ring. You may hear piano music weekday afternoons, since I give lessons (usually 3-6 pm; a bit earlier in summer) NEW HEATED FLOORS w/thermostat

Top guest favourite
Flat in Winona
4.95 out of 5 average rating, 266 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * NO cleaning fee/deposit required * Spacious bedroom with queen size bed, couch and workspace * Fully kitchen with oven, refrigerator, microwave + coffee/tea station * TV, board games and books * All amenities needed for a comfortable stay * Walking distance to WSU and Cotter * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

Top guest favourite
A cozy bedroom features a spacious bed with neatly arranged pillows and a navy throw blanket. Two lamps illuminate the nightstands flanking the bed. Wall art and a large mirror enhance the inviting atmosphere, while natural light filters in through nearby windows.
Flat in Rochester
4.93 out of 5 average rating, 165 reviews

Home for the Traveler, a walk to St. Mary's

This place is located near the heart of Rochester, within blocks of St. Mary's hospital, very peaceful, cozy and private. A lower-level unit in an older home, plenty of windows and light, and includes a gorgeous bedroom with a fireplace, a full kitchen, a reading room, and a clean, updated bathroom. This home is also close to the Apache mall, the Canadian Honker and other local restaurants, coffee shops, and the walking/biking trail system. There is also Wi-Fi, laundry, and parking on-site.

Top guest favourite
A view of the Mississippi River is seen from the apartment, with lush green bluffs in the background. Nearby buildings exhibit charming architecture, and parked cars line the streets. A light post adorned with an American flag stands in the foreground.
Flat in Trempealeau
4.98 out of 5 average rating, 139 reviews

Small Town Vibes with Amazing River & Bluff Views

Enjoy gorgeous view of the Mississippi River, bluffs, and trains, entertain yourself with the live music (occasionally late) from neighboring establishments, stargaze on the deck, or revel in the passing trains. This apartment is the perfect place to get away and relax. Bring up your boat as you'll have parking available in the driveway too! NOTE: this is an upstairs apartment, but we promise you won't be disappointed and want to come back again and again. NON SMOKING. No pets.

Top guest favourite
A cozy living room space features a beige couch adorned with decorative pillows and a low coffee table. The white brick wall serves as a backdrop for a fireplace, which is framed by a wooden mantle decorated with artwork and a wreath. Natural light enters through a window.
Flat in Rochester
4.97 out of 5 average rating, 255 reviews

Restful sanctuary close to Mayo Clinic

This cozy space has private, self-entrance with off-street parking at no cost...a mere 2.5 miles or 10 minute drive to the Mayo Clinic downtown. Located in a quiet neighborhood in northwest Rochester. Easy access to highways, grocery store, coffee shop, Target, restaurants and biking/walking trail. Completely furnished with linens, hair-dryer, Netflix and Hulu, Smart TV and Wi-fi....and a Keurig Coffee maker with enough coffee pods to get you started. Truly, a home away from home!

Top guest favourite
A serene lakeside view is presented at sunset, with vibrant colors reflected on the water. Tall trees border the scene, and a grassy area leads toward the water's edge. A dock is visible, positioned for easy access to the lake.
Flat in Onalaska
4.81 out of 5 average rating, 204 reviews

Northshore Studio on Lake Onalaska

Lakefront studio where retro and rustic charm meets modern convenience. Studio offers everything you need for a relaxing and enjoyable stay including a queen-sized bed, a living area with a Roku TV, a full kitchen and a bathroom with a step in shower. The lakefront screen porch provides the perfect spot to enjoy your morning coffee or unwind with a good book. Two sit on top kayaks are included. Bikes are available and hiking and biking trails are just across the street.

Top guest favourite
A modern living area features a dark sofa complemented by a vibrant orange chair. A decorative area rug with blue and orange patterns adds warmth. Natural light filters through three windows, illuminating the stylish decor and shelving on the wall.
Flat in Viroqua
4.93 out of 5 average rating, 169 reviews

Bright two bedroom rental in the heart of downtown

Enjoy a comfortable experience at this centrally-located rental, just steps away from downtown Viroqua. Grab a coffee at Wonderstate Cafe before heading over to the farmers market right next door. Explore the thriving art scene and local shops, before finishing off the evening with a dinner at the Driftless Cafe. This will also make a great homebase for hiking, biking, fishing, and paddling out in the great Driftless area. We love our little town, and hope you do too!

Top guest favourite
The serene lake is captured at sunset, reflecting soft hues of orange and pink across the calm water. Gentle ripples can be seen, with distant hills framed against the colorful sky. The scene evokes a peaceful atmosphere, showcasing the lakeside setting.
Flat in Onalaska
4.89 out of 5 average rating, 247 reviews

Lakefront Studio

Lakefront studio One bedroom studio on the edge of the Upper Mississippi Wildlife Refuge. Surrounded on one side by beautiful Lake Onalaska with prairie walking trails on the other. You will not find a closer view of Lake Onalaska. There are two public boat landings less than a mile away. Stay and experience all that "God's Country" has to offer. Now sleeps three: We’ve added a new folding cot to accommodate an extra guest. *No cleaning fees*

Top guest favourite
The exterior of a two-story apartment building is shown, featuring a balanced facade with large windows and a welcoming front entrance. Shallow steps lead to the door, which is flanked by decorative lights. Lush greenery surrounds the property, including shrubs and trees, offering a serene appearance.
Flat in La Crosse
4.86 out of 5 average rating, 178 reviews

Charmer on 19th and Cameron

Main level apartment in highly desirable La Crosse neighborhood . Locals choose this area for it’s convenience, charcter, and accessibility to nearby restaurants and parks. We can’t wait to share that experience with you! The beautifully maintained woodwork and fireplace will make you fall in love inside. The private, shaded backyard coupled with friendly local walking about will make you with you could stay forever! License number MWAS-D5ZSF2

Top guest favourite
A comfortable sitting area features a dark gray sectional sofa paired with a white accent chair. A lamp stands beside the sofa, providing soft light. The window, dressed with dark curtains, allows natural light to filter in, illuminating the space.
Flat in Viroqua
4.89 out of 5 average rating, 288 reviews

One Bedroom with Kitchenette - Red Door

Our convenient in-town one-bedroom has recently been converted! One room has a queen bed, other room as a comfy fold out couch. It has a well-equipped kitchenette with a sink, microwave, apartment fridge/freezer, Kuerig coffee maker and more. It also has a full bath. This apartment is on Main Street and can be a bit noisy from the traffic during the day and in the morning. It is generally quieter at night but bring earplugs if this bothers you.

Top guest favourite
An open-concept living area features a spacious dark green couch and a wooden coffee table placed on a patterned rug. A dining table with chairs is positioned in the background, with the kitchen visible, showcasing updated appliances and cabinetry.
Flat in La Crosse
4.98 out of 5 average rating, 123 reviews

Buddha’s Cloud

Unique, centrally-located and freshly updated upstairs apartment in duplex. We’ve done our best to freshen this private second floor unit in our old ugly home. Amish made kitchen cabinets, island and furniture. New appliances and fixtures. View granddad’s bluff out the bedroom window! Close to UWL, Viterbo, Mayo Clinic, and downtown (8 block walk to 3rd street). We currently live in the downstairs apartment with our dogs.

Top guest favourite
A back deck with a river view is furnished with two comfortable chairs and a small table, allowing for relaxation and enjoyment of the scenic landscape. The backdrop features lush trees and the Mississippi River, with a bridge visible in the distance under a clear blue sky.
Flat in Wabasha
4.98 out of 5 average rating, 279 reviews

Spacious River View 2 br apt near Eagle Center

Discover this hidden gem in the heart of Wabasha! This fully renovated 2BR/2BA apartment blends historic charm with modern comfort. Walk to the Eagle Center, riverfront bandstand, and downtown dining. Enjoy a new kitchen, spacious living/dining room, fireplace, and large deck with Mississippi River views—all fully furnished for your stay. Plus, get 50% off the Wild Wings golf simulator in Lake City when you book!

Popular amenities for Winona apartment rentals

When is the best time to visit Winona?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$125 SGD$122 SGD$111 SGD$115 SGD$144 SGD$146 SGD$157 SGD$158 SGD$142 SGD$140 SGD$132 SGD$120 SGD
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Quick stats about flat rentals in Winona

  • Total holiday rentals

    Explore 20 holiday rentals in Winona

  • Nightly prices starting at

    Winona holiday rentals start at $78 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,520 verified reviews to help you choose

  • Wifi availability

    20 of Winona holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winona rentals

  • 4.9 Average rating

    Winona stays are highly rated by guests – averaging 4.9 out of 5!

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