
Apartment vacation 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.

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

~ Third Street Suites ~ #7
This beautiful 3rd story- 2 level penthouse apartment (ACCESSED BY STAIRS ONLY UP TO 3RD LEVEL ) is conveniently located in the heart of downtown Winona MN! Everything Winona and the downtown area has to offer is within close proximity. Examples include: Coffee, restaurants, bars, brewery, Winona State University, Mississippi , 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!

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.

Sunny & Historic 1 Bedroom Haven- Main St, Viroqua
Located *truly* steps away from everything on bustling Main Street, Viroqua, make yourself at home in our sunny 2nd floor one bedroom apartment. In the morning feel free brew yourself coffee or grab a vintage basket and stroll down to the local Shops. In case you'd like to eat out, you're conveniently located within two blocks of several different hot spots in our sweet town. (Our favorites are Driftless Cafe, Maybe Lately’s, Tangled Hickory & Wonder State Coffee Cafe.)

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.

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!

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

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.

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*

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

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.

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.
Popular amenities for Winona apartment rentals
Weekly apartment rentals

Pepin Guest Haus - walk to the winery!

Highland Place St. Charles

Spacious 1 bed 1 bath apt #5D

Sweet Retreat in Lanesboro~

Zumbro Valley Getaway

Great Location! 2 Bedrooms! Country in the City!

Farmhouse Apartment - River Road Historic Home

Big River Inn - River view apartment in Alma
Private apartment rentals

Quiet Country Comfort w Long Views

The Snapdragon

Hokah Ohana House: Historic charm, Modern updates

The Original: One-of-a-kind downtown apartment

Two story apartment, spacious!

Small Town Getaway

Waterfront Mississippi River Retreat

River life!
Family-friendly apartment rentals

EXCEPTIONAL, CONTEMPORARY 2BD/1 BA/ CLOSE TO MAYO

Spacious Riverside 2Bed/2Bath w/Balcony near Mayo

NEW: Calming main floor retreat near Mayo Clinic

Discount Charming 2 Bedroom Close to Mayo

Lux 1 BR I 1 Block to Mayo Skyway I Parking I Pets

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

Restful sanctuary close to Mayo Clinic

Driftless Suite -outside Hot Tub
When is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ353 | ﺩ.ﺇ342 | ﺩ.ﺇ312 | ﺩ.ﺇ323 | ﺩ.ﺇ404 | ﺩ.ﺇ411 | ﺩ.ﺇ441 | ﺩ.ﺇ444 | ﺩ.ﺇ400 | ﺩ.ﺇ441 | ﺩ.ﺇ364 | ﺩ.ﺇ312 |
| Avg. temp | -7°C | -5°C | 2°C | 10°C | 16°C | 22°C | 24°C | 23°C | 18°C | 11°C | 3°C | -4°C |
Quick stats about apartment rentals in Winona

Total vacation rentals
Explore 30 vacation rentals in Winona

Nightly prices starting at
Winona vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 4,830 verified reviews to help you choose

Wi-Fi availability
30 of Winona vacation rentals include wi-fi 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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