Apartment holiday rentals in Winona

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Top-rated apartment rentals in Winona

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Guest favourite
The exterior of a charming Victorian home is displayed, featuring a light yellow façade complemented by a dark shingled roof. A decorative porch wraps around the front, adorned with hanging plants. Large windows provide an inviting glimpse into the beautifully maintained structure.
Flat in La Crosse
4.97 out of 5 average rating, 135 reviews

Morris House Apartment

The Morris House Apartment is a completely separate, one bedroom apartment on the second floor of a beautiful Victorian home built in 1895 for Thomas Morris, founder of the University of WI-La Crosse. We are conveniently located just a five minute walk to the university and a ten minute walk to a thriving downtown area. We offer a spacious living area, fully equipped kitchen, off-street parking, two private entrances and a screened private porch. Come & enjoy! License # MWAS D6KQEV

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, 141 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 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 room features a blue memory foam sleeper sofa paired with two light-colored accent chairs. A 65” Roku TV displays various streaming options on a dark accent wall. A vibrant piece of artwork, depicting trees in autumn, adds a colorful touch to the space.
Flat in La Crosse
4.99 out of 5 average rating, 194 reviews

Clean 2BR Apt by Mayo, 50-ft Parking

Clean, comfy 2BR apartment on the second floor of a duplex (20 steps to enter) with modern design and art from Thailand and Vietnam. 5-min walk to Mayo/Viterbo and 5-min drive to downtown/UWL. We can’t wait to host you. Enjoy these extras for a great stay: ★ Helix mattresses ★ 300 Mbps Wi-Fi & 65" Roku TV ★ Free off street parking (two 50 ft spaces) ★ Desk and monitor ★ K-Cup coffee maker ★ Full-length mirrors ★ USB/outlet hubs ★ Sound machines ★ HEPA air purifier

Top guest favourite
Flat in Winona
4.95 out of 5 average rating, 274 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * 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.

Superhost
A spacious bedroom features a large bed with crisp white linens, accompanied by two bedside tables with lamps. Natural light filters through a window adorned with blue curtains, and a shelf is positioned against the wall for added storage.
Flat in Wabasha
4.82 out of 5 average rating, 219 reviews

Charming Oasis in the Heart of Historic Downtown

A beautiful getaway right in the heart of iconic Wabasha, Minnesota. With a view of the Mississippi from the porch this top level apartment is the perfect landing pad for all visitors! The duplex is less than a block from the National Eagle Center, the Mississippi River and all of downtown Wabasha. Decorated beautifully with all brand new tuft and needle beds you will definitely sleep well and be able to embrace this small town lifestyle on foot.

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, 187 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

Superhost
The spacious living room showcases large windows allowing natural light to fill the area. A comfortable sectional and a plush sofa are positioned around a central coffee table. A television is mounted on the wall, while decorative accents are displayed on a wooden shelf.
Flat in La Crosse
4.79 out of 5 average rating, 107 reviews

Downtown La Crosse Modern Flat

Experience the charm of downtown La Crosse, Wisconsin in this beautifully renovated flat featuring exposed brick and an industrial-style ceiling. Enjoy a comfortable, modern space with a high-end kitchen complete with granite countertops. The home offers two cozy bedrooms, plus a pull-out couch and sleeper chair for extra guests. Private parking is available, and you’re just steps away from restaurants, shops, and local events.

Top guest favourite
An open living space showcases a blend of natural wood and stone elements. A large dining table is positioned near a cozy seating area, featuring a modern couch and chair arrangement. A fireplace serves as a focal point, with natural light coming through large windows revealing a view of the Mississippi River.
Flat in Lake City
4.99 out of 5 average rating, 102 reviews

22 Paradise View

Stay at 22 Paradise View! This renovated historic 2nd-floor apartment boasts stunning Mississippi River views and a walkable downtown Lake City location. Relax in the king master suite with a spa-like bath featuring a rain shower and clawfoot tub. Extra guests will love the Murphy beds, plus you’ll have a full kitchen, 1.5 baths, and cozy fireplace. Bonus: get 50% off the Wild Wings golf simulator when you book with us!

Top guest favourite
A spacious living area features a sectional couch adorned with throw pillows, set beside a wooden coffee table. A well-equipped kitchen is visible, showcasing modern appliances and ample countertop space. Natural light filters through two skylights, enhancing the open and airy feel of the room.
Flat in Winona
4.99 out of 5 average rating, 636 reviews

~ Third Street Suites ~ #10

Hi! This beautiful main level apartment is conveniently located in the heart of downtown Winona MN! Everything Winona has to offer is within close proximity. Examples include: Coffee, restaurants, a wine bar, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next stay in beautiful Winona a memorable one!

Guest favourite
A spacious living area features two comfortable sofas and a rustic coffee table atop a decorative rug. A television is positioned against the wall, while natural light fills the room through archways leading to adjacent spaces.
Flat in La Crosse
4.96 out of 5 average rating, 178 reviews

Bluff View Victorian - Free Bikes included

Modern Victorian home, dates back to La Crosses Lumber mill days. Built by the Molzahn family in 1895, key features included open concept with tons of natural light. Located one of the best neighborhoods in La Crosse. This is the upper unit of the house, stairs are required to get into the unit. Key pad for easy entrance. We look forward to having you! Well trained & behaved pets welcome. Pet fee of $50.00 each. Max 2

Superhost
A bright living room features large windows allowing natural light to fill the space. A comfortable sofa is positioned opposite a low coffee table, while dining chairs surround a rustic table. Indoor plants are placed on surfaces, contributing to the natural decor.
Flat in La Crosse
4.73 out of 5 average rating, 159 reviews

Historic Upper Apartment in Heart of Downtown

Large, 3 bedroom, 1 bath second floor apartment. Bright open concept living room and kitchen overlooking 4th Street, great for large or small groups. Charming natural decor highlights this updated vintage space. Amenities galore: Fully equipped kitchen and basic bathroom needs, WiFi, smart TV, laundry, workspace, and one designated parking spot (plus access to safe ramp parking less than a block away).

Popular amenities for Winona apartment rentals

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Avg. price£71£69£63£65£82£83£89£90£81£89£73£63
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Quick stats about flat rentals in Winona

  • Total holiday rentals

    Explore 30 holiday rentals in Winona

  • Nightly prices starting at

    Winona holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 4,830 verified reviews to help you choose

  • Wifi availability

    30 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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