
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$12,537 GYD per night before taxes and fees

Verified guest reviews
Over 5,720 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!
Top-rated apartment rentals in Winona
Guests agree: these apartments are highly rated for location, cleanliness, and more.

Hokah Ohana House: Historic charm, Modern updates
Bright & airy upstairs 2 bedroom apartment boasts historic charm with a Hawaiian feel. Relax, unwind & slow down to "island time" in the comforts of this updated space. Located in the heart of our small downtown in the Driftless Region, you can explore the nearby rivers, bluffs and falls or stay in and escape from the hustle & bustle of your daily routine. *Ladybugs, boxelder beetles & house flies are common in our rural area, we treat the exterior of the building to reduce their presence.

~ Third Street Suites ~ #1
This beautiful 2nd story suite (accessed by stairs only) is conveniently located in the heart of downtown Winona MN on Third Street! Everything Winona and the downtown area has to offer is within close proximity. Examples include: Coffee shops, restaurants, cocktail lounges, bars, brewery, Winona State University, Mississippi River, Lake Winona, hiking Shakespeare Festival, Minnesota Marine Art Museum, & much more! Please allow us to make your next stay in beautiful Winona a memorable one!

Two story apartment, spacious!
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, upon request. Pets are welcome. Located a very short walk to Sylvan Park which has a wonderful playground. Plenty of counter space for a gathering. You’re welcome to park your bikes inside the apartment if you don’t mind bringing them up the exterior stairs. :)

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.

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.

Treetops Suite, 2 bedrooms @ 7th Street Retreat
Treetops Suite for Four is the perfect weekend getaway, conveniently located in the heart of Winona and only a 7-minute walk from the train station. The self check-in apartment has a secure keypad entrance. 2 bedrooms, 1 double bed and 2 twin beds, bathroom w/shower, kitchenette and sitting area. Wi-Fi; Cable, Netflix/Prime/DVD player. Please use caution on the steep steps to the apartment. There is a hand railing. We are located three blocks from a charging station.

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

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. The property is family-owned and operated and has been offered for vacation rentals since the 1960s. 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. *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

Luxury Downtown La Crosse Apartment - Sleeps 8!
Experience the best of La Crosse in this spacious 4-bedroom downtown apartment, perfect for families and groups. Enjoy comfortable sleeping arrangements, a large sectional, premium sound system, fully equipped kitchen, and modern amenities. Located steps from restaurants, shops, nightlife, and local attractions, this stylish space offers the perfect blend of comfort and convenience for your next getaway in downtown La Crosse.

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.
Popular amenities for Winona apartment rentals
Weekly apartment rentals

Charming Oasis in the Heart of Historic Downtown

The Bridge View

Entire cozy Rollingstone apt. 10 min to Winona!

Riverview Apartment - River Road Historic Home

Historic Withee Home / 3rd Level / Sleeps 2

River Road Hideaway

Great Location! 2 Bedrooms! Country in the City!

The Aberdeen St. Charles, MN
Private apartment rentals

Pepin Marina Retreat: Cottage Apartment with Deck

Pepin Guest Haus - walk to the winery! Sauna!

Sweet Retreat in Lanesboro~

Small Town Getaway

* New! Beautiful downtown Apartment on Pearl St

Stunning Mississippi River Loft

Waterfront Mississippi River Retreat

Parkway Place - A
Family-friendly apartment rentals

Sunny & Historic 1 Bedroom Haven- Main St, Viroqua

One Bedroom with Kitchenette - Red Door

Bright two bedroom rental in the heart of downtown

Homey & Historic 2 Bedroom Haven- Main St, Viroqua

Viroqua Studio With a Backyard View

Main Street Viroqua Apartment

Quiet Country Comfort w Long Views

Small Town Vibes with Amazing River & Bluff Views
When is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$18,597 GYD | G$19,015 GYD | G$19,641 GYD | G$18,388 GYD | G$22,985 GYD | G$23,403 GYD | G$25,074 GYD | G$25,283 GYD | G$22,776 GYD | G$25,074 GYD | G$20,686 GYD | G$17,761 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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