
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$12,554 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.

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.
4.95 out of 5 average rating, 244 reviews
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.
4.93 out of 5 average rating, 103 reviews
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. :)
4.93 out of 5 average rating, 138 reviews
"Escape to the Northwoods of Onalaska!" 7
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.
4.84 out of 5 average rating, 101 reviews
Pepin Marina Retreat: Cottage Apartment with Deck
We are right across from the Pepin Marina and Beach, next door to Bear Fish Brew Coffee House, and steps away from the iconic Harbor View Cafe! You can book sailing and pontoon rides on the lake. The Pickle Factory, a waterfront grill and bar, features live music, bingo and more. Up the hill is the River Time bar, which also features live music and small plates. We are one mile away from the Villa Belleza Winery. There's lots to see and do along all the nearby river towns!
4.89 out of 5 average rating, 101 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.
4.83 out of 5 average rating, 228 reviews
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*
4.95 out of 5 average rating, 136 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
4.88 out of 5 average rating, 226 reviews
1 Bedroom with Extra Amenities, Quiet Neighborhood
Our light-filled two-bedroom apartment is the perfect home away from home in Winona. * Spacious main bedroom with queen size bed * Second bedroom with twin daybed and 90s throwback CRTV * 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
4.95 out of 5 average rating, 293 reviews
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.
4.91 out of 5 average rating, 129 reviews
Cozy 3BR Apartment near Mayo
Clean, cozy 3BR ground floor apartment in a duplex (5 steps to enter) with modern boho design. 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 & 55" Roku TV ★ Free off-street parking (two 50-ft spaces) ★ Velvet couch ★ K-Cup coffee maker ★ Full-length mirrors ★ USB/outlet hubs ★ Sound machines ★ Card games
5.0 out of 5 average rating, 218 reviews
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!
4.98 out of 5 average rating, 332 reviewsPopular amenities for Winona apartment rentals
Weekly apartment rentals

Bluff View Victorian - Free Bikes included
4.96 out of 5 average rating, 187 reviews
Charming Oasis in the Heart of Historic Downtown
4.81 out of 5 average rating, 234 reviews
Hokah Ohana House: Historic charm, Modern updates
4.9 out of 5 average rating, 103 reviews
The Bridge View
4.96 out of 5 average rating, 24 reviews
Entire cozy Rollingstone apt. 10 min to Winona!
5.0 out of 5 average rating, 50 reviews
Historic Withee Home / 3rd Level / Sleeps 2
4.9 out of 5 average rating, 61 reviews
Riverview Apartment - River Road Historic Home
4.91 out of 5 average rating, 32 reviews
Big River Inn - River view apartment in Alma
4.9 out of 5 average rating, 42 reviewsPrivate apartment rentals

River Road Hideaway
4.96 out of 5 average rating, 57 reviews
Welcome to the Cheese Cave!
5.0 out of 5 average rating, 14 reviews
Sweet Retreat in Lanesboro~2 bedroom apartment
4.98 out of 5 average rating, 59 reviews
The Snapdragon
4.98 out of 5 average rating, 45 reviews
Stunning Mississippi River Loft
4.95 out of 5 average rating, 37 reviews
Top Shelf Suite
5.0 out of 5 average rating, 25 reviews
2 Bedrooms! Great Location! Country in the City!
5.0 out of 5 average rating, 70 reviews
The Original: One-of-a-kind downtown apartment
4.92 out of 5 average rating, 83 reviewsFamily-friendly apartment rentals

Adorable 2BR in La Crosse - Pet Friendly
4.92 out of 5 average rating, 71 reviews
Grandma's Trail House: Top Floor
5.0 out of 5 average rating, 27 reviews
Charming 2 Bedroom Apt & Patio, Historic District
4.93 out of 5 average rating, 40 reviews
Historic Upper Apartment in Heart of Downtown
4.73 out of 5 average rating, 179 reviews
Cozy & Fully Remodeled 1-Bedroom Retreat
4.83 out of 5 average rating, 6 reviews
Unbeatable Location! Large Deck & Firetable!
5.0 out of 5 average rating, 24 reviews
Lake Boulevard House
4.61 out of 5 average rating, 18 reviews
The Exchange 14 | Historic Bldg, Studio, Dwntwn
4.85 out of 5 average rating, 41 reviewsWhen is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$18,622 GYD | G$19,041 GYD | G$19,668 GYD | G$20,087 GYD | G$23,853 GYD | G$21,970 GYD | G$25,109 GYD | G$25,318 GYD | G$22,807 GYD | G$25,109 GYD | G$20,715 GYD | G$17,785 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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