
Apartment vacation rentals in Winona
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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 G$12,555 GYD per night before taxes and fees

Verified guest reviews
Over 5,050 verified reviews to help you choose

Wi-Fi availability
20 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!
Top-rated apartment rentals in Winona
Guests agree: these apartments are highly rated for location, cleanliness, and more.

Buddha’s Nest
Smatterings of Asian decor mixed with a longing for the knowledge of the sacred wheels of life invite you into a comfortable flat protected by Buddha who will watch over you while you sleep. Buddha’s Nest has been completely updated, including Nepalese art and a comfortable sitting area for you to learn or practice meditation. Enjoy your own porch that overlooks the back yard. Centrally located. Easy access to the beach, bluffs, campus, groceries, I90, downtown and our neighborhood bar, Genzies.

Treetops Suite, 1 Bedroom @ 7th Street Retreat
Treetops for 2 is located in the heart of Winona a 7-minute walk from train station. The apartment has a secure, self check-in entrance located at the back of the house, has 1 BR (double bed), bathroom (shower), kitchenette and living area. It has a remote controlled heating/cooling system, cable and internet-enabled TV/DVD, and Wi-Fi. Guests share the driveway, back entrance, laundry room, and back patio. The steps up to the apartment are steep. The space is 3 blocks from a charging station.

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.

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.

1 Bedroom with Extra Amenities, Quiet Neighborhood
Our light-filled one-bedroom apartment is the perfect home away from home in Winona. * Spacious bedroom with queen size bed * Hardwood floors throughout * Full kitchen with oven, refrigerator, microwave + coffee/tea station * Within walking distance of Winona State University and Cotter High School * Located on the ground floor with parking * 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.

Viroqua Studio With a Backyard View
Formerly Del Sol Chocolate factory, the space is in a quiet, residential area close to Eckhart Park and within walking distance to all of the great spots. Apartment is an addition off of the back of my house, with views into the backyard, and with a private entrance. The apartment features a full bathroom with a shower, and also a kitchenette. (small frig., toaster oven, french press). Wifi is available, and also internet access with ethernet is. Fragrance free.

Waterfront Studio
Waterfront studio The studio is 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. The property is family-owned and operated and has been offered for vacation rentals since the 1960s. Stay and experience all that "God's Country" has to offer. *No cleaning fees*

Downtown La Crosse Loft: Modern Comfort & Style
Experience comfort and convenience in this stylish 3-bedroom La Crosse apartment, perfect for families and groups. The spacious home includes 2 full bathrooms, a fully equipped kitchen, and in-unit laundry. Enjoy 2 dedicated parking spaces and a prime location near local attractions, dining, and entertainment. Ideal for short getaways or longer stays, this welcoming apartment offers all the modern essentials for a relaxing and memorable visit to Wisconsin.

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.

Two story apartment, spacious!
The whole group will be comfortable in this spacious and unique space. This is a furnished apartment in a renovated church. One bedroom with a queen bed and large walk in closet on the lower level. A stairway takes you to an upper loft with three twin beds. Pack n play available and high chair too. Pets are welcome. Located a very short walk to Sylvan Park which has a wonderful playground. Plenty of counter space for a gathering.

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!
Popular amenities for Winona apartment rentals
Weekly apartment rentals

Polyshades of Gray

Clean 2BR Apt by Mayo, 50-ft Parking

Homey & Historic 2 Bedroom Haven- Main St, Viroqua

Sunny & Historic 1 Bedroom Haven- Main St, Viroqua

Charmer on 19th and Cameron

Entire cozy Rollingstone apt. 10 min to Winona!

Historic Withee Home / 3rd Level / Sleeps 2

Cozy & Private Viroqua Apartment near Downtown
Private apartment rentals

Red Ram Deckhouse

Pepin Guest Haus - walk to the winery! Sauna!

The Snapdragon

Highland Place St. Charles

Welcome to the Cheese Cave!

Great Location! 2 Bedrooms! Country in the City!

Small Town Getaway

Renovated Deluxe King Studio Apt
Family-friendly apartment rentals

Mabel Manor on Main Street

Quiet Country Comfort w Long Views

Riverview Apartment - River Road Historic Home

Spacious 1 bed 1 bath apt #5D

Sweet Retreat in Lanesboro~

Lake Boulevard House

The Exchange 14 | Historic Bldg, Studio, Dwntwn

The Bridge View
When is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$18,624 GYD | G$19,042 GYD | G$19,670 GYD | G$18,414 GYD | G$23,018 GYD | G$23,436 GYD | G$25,110 GYD | G$25,320 GYD | G$22,809 GYD | G$25,110 GYD | G$20,716 GYD | G$17,787 GYD |
| 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 |
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