Apartment holiday rentals in Winona County

4.2 out of 5 average rating, 5 reviews

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.

4.94 out of 5 average rating, 253 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * NO cleaning fee/deposit required * 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.

Apartment in Rollingstone

5 out of 5 average rating, 32 reviews

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.

Apartment in Fountain City

River View Flat

The River View Flat is a wonderful property overlooking the grand Mississippi river. Amazing views throughout the suite. Comfortably sleeps 2 with a queen bed. All utilities included, including free high speed wifi. The suite also features a large private 3-season porch, outdoor grill/relaxing area, and access to the sites basketball court. Located two blocks from the public boat landing. The property is located in a small river, wine, and cheese community just outside of Winona, MN.

4.98 out of 5 average rating, 133 reviews

Apartment in Trempealeau

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.

Apartment in Fountain City

4.93 out of 5 average rating, 28 reviews

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.

4.87 out of 5 average rating, 46 reviews

The Exchange 11 | Historic Bldg, 1 BR, 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.

Apartment in Saint Charles

4.86 out of 5 average rating, 7 reviews

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, both with queen beds, 1 bathroom, and a game area with a foosball table for a fun night in! This upper level condo sleeps up to 5 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.

4.93 out of 5 average rating, 92 reviews

Treetops Suite, 1 Bedroom @ 7th Street Retreat

Treetops for 2 is located in the heart of Winona. The upstairs 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.

4.89 out of 5 average rating, 242 reviews

Apartment in Onalaska

Lakefront Studio

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. 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. Now sleeps three: We’ve added a new folding cot to accommodate an extra guest. *No cleaning fees*

4.98 out of 5 average rating, 343 reviews

~ Third Street Suites ~ #8

Hi! This beautiful main level apartment is conveniently located in the heart of downtown Winona MN! Everything Winona has to offer is within close proximity. Examples include: Coffee, restaurants, bars, wine bar, 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!