
Apartment holiday rentals in Winona
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Top-rated apartment rentals in Winona
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Escape to the "Northwoods" of Onalaska! 5
Escape to the "Northwoods" of Onalaska! This guest room is next door to our restaurant, Red Pines Bar & Grill so a stay here means access to a full-service restaurant & bar, volleyball courts, the lake and great people. We are always available if you need anything during your stay. We also have our Red Pines Cafe open 7:30 am seven days a week when the main restaurant is closed. There are 5 other rooms in Red Pines Lodging so the space is basically a hotel with your own private access.

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

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.

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.

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

~Third Street Suites ~ #4
This beautiful 2nd story loft suite (accessed by stairs only) 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 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!

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.

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

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.

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

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!

Downtown La Crosse Modern Flat
Experience the best of downtown La Crosse, Wisconsin, where the Driftless Area’s natural beauty meets a lively city atmosphere. Located on 3rd Street, you’ll be perfectly positioned between the Mississippi River to the west and Grandad Bluff to the east. Whether you’re in town for work, a weekend getaway, or outdoor adventure, dining, shopping, and entertainment are all just steps away.
Popular amenities for Winona apartment rentals
Weekly apartment rentals

Charming 2 Bedroom Apt & Patio, Historic District

Grandma's Trail House: Top Floor

Parkway Place - A

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

Mayoral Suite Above Paddle On

Above the Barrel

Lake Boulevard House

The Hub Hideaway
Private apartment rentals

Highland Place St. Charles

Auggie's home away from home

Charming Oasis in the Heart of Historic Downtown

Entire cozy Rollingstone apt. 10 min to Winona!

Historic Withee Home / 3rd Level / Sleeps 2

Farmhouse Apartment - River Road Historic Home

Serene River View Loft

The Exchange 11 | Historic Bldg, 1 BR, Dwntwn
Family-friendly apartment rentals

Heart of down town La Crosse

Charming 2 bed near hospitals!

Pepin Guest Haus - walk to the winery!

Summer on the Water! Studio with Water Access!

Hawks View's La Crescent Suite

Updated 2 Bedroom by Wedding Venues w/ Bonfire

Hidden Gem - 1BR/1Bath in Lax WI

Swan Suite River front comfort
When is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $124 SGD | $120 SGD | $110 SGD | $113 SGD | $142 SGD | $144 SGD | $155 SGD | $156 SGD | $140 SGD | $138 SGD | $130 SGD | $119 SGD |
| 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 flat rentals in Winona

Total holiday rentals
Explore 30 holiday rentals in Winona

Nightly prices starting at
Winona holiday rentals start at $77 SGD 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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