Apartment holiday rentals in Winona County

Lake Boulevard House

“Lake Boulevard House” is nestled in the bluffs under Sugar Loaf in charming Winona Minnesota! This downstairs dwelling features picturesque views of Winona lake. This centrally located home offers: 1 bedroom features a single trundle bed that comfortably sleeps two guests. 1 sectional couch that converts to a queen bed. Linens and pillows provided. 1 bathroom with standing shower and towels Kitchenette features a fridge/freezer, stocked Keurig coffee machine, air fryer, and microwave.

Location · Family · Comfort

Highland Place St. Charles

Welcome to our cozy home away from home that overlooks the beautiful St. Charles main street. The Highland Place features 2 bedrooms, one with a King bed and one with a queen, 1 bathroom, and a game area with a foosball table for a fun night in! This upper level condo sleeps up to 4 people and is steps away from the main street attractions. Highland Place is a short 25 minute drive from Rochester and Mayo Clinic, 30 minute drive from Winona, and a short 10 minute drive to Whitewater State Park.

Family · Location · Access

Top Guest favourite

Guest favourite

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.

Location · Value · Hospitality

Top Guest favourite

Guest favourite

Entire cozy Rollingstone apt. 10 min to Winona!

In town it's simply known as “Hattie’s”, and she's always been known for her kind smile. Whether you're planning family visits or local adventures, we hope you love staying at Hattie’s. Just 10-mins. from Winona (WSU/St. Mary’s University), Whitewater State Park & Prairie Island, hiking, biking, snowmobiling, hunting, kayaking, boating, fishing & wineries. Hattie's is an entire apt. above once Jung and River’s Mercantile (1850s) combining comfy old and new, with a touch of Luxemburg history.

Value · Family · Parks

Riverview Apartment - River Road Historic Home

Beautifully restored 1898 Victorian with River View! The Riverview Apartment is located within the 1898 Joseph Fugina Historic Home and contains 3 bedrooms, 3 bathrooms, private living room, kitchen, balcony, back deck, and laundry in home. Amazing panoramic Mississippi River Views from nearly every room. Outside patios and seating available, as well as wrap-around porch, balcony, and back deck with gas grill! Stay connected with fast Wi-Fi and TVs in every bedroom and living room.

Location · Family · River

The Exchange 14 | Historic Bldg, Studio, Dwntwn

Newly renovated, The Exchange offers comfort and modern amenities surrounded by old world charm. Located in the historic district of this spectacular river town, you can experience and explore the culture and natural playground that is Winona. The Exchange was built in 1900 as the commodities exchange for ship and rail transport coming along the Mississippi River. Keep an eye out throughout the building for subtle mentions to the past and the stories this unique building holds.

Value · Location · Quiet

Top Guest favourite

Guest favourite

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.

Location · Family · TV

Top Guest favourite

Guest favourite

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*

Value · Family · Biking

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 cozy 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

Location · Family · Condition

Unbeatable Location! Large Deck & Firetable!

This newly renovated apartment in the heart of downtown Winona was thoughtfully designed for guests who value both comfort and character. Set within one of Winona’s most historic buildings, nearly every piece inside has been thoughtfully collected to create a space that feels both refined and rooted in Winona’s rich history. You will stay just steps from the riverfront, dining, bars and cultural attractions.

Value · Location · Kitchen

Top Guest favourite

Guest favourite

The Bridge View

Bright, spacious retreat in the heart of Winona! This stylish unit at 129 W 3rd St features warm hardwood floors, high ceilings, and large bay windows with abundant natural light. Enjoy a cozy bed, modern furnishings, and a relaxing sitting area. Walk to downtown, the Mississippi River, shops, and dining—perfect for a comfortable and convenient stay.

Location · Value · View

Cozy & Fully Remodeled 1-Bedroom Retreat

Cozy remodeled 1-bed, 1-bath retreat in Winona. Features a private entrance, modern kitchen, in-unit washer/dryer, and relaxing yard. Utilities & Wi-Fi included. Steps from Winona Health, close to Mayo & Gundersen, and near Lake Winona parks and trails. Ideal for travel nurses or long stays. This is a second-floor unit. *There are stairs*

Location · Walkability · TV