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Holiday rentals in Winona

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Top-rated holiday rentals in Winona

Guests agree: these stays are highly rated for location, cleanliness, and more.

Loft in Winona
Penthouse Retreat-Near Downtown Winona!
Hi! This beautiful loft is conveniently located in the heart of Winona MN! Only a few blocks from the downtown and in close proximity to many other attractions Winona has to offer such as: Coffee, restaurants, a 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 extended stay in beautiful Winona a memorable one! * MUST CLIMB STAIRS TO UNIT- LOCATED ON THE 3RD LEVEL
₹8,108 per night
Flat in Winona
Entire 2nd Floor Apt with Extra Amenities
Our newly-remodeled one-bedroom apartment is the perfect getaway for two guests. * Spacious bedroom with queen size bed, couch and workspace * Hardwood floors throughout * Full kitchen with oven, refrigerator, microwave + coffee/tea station * Walking distance to WSU and Cotter * Located on the 2nd floor with off-street parking * 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.
₹7,834 per night
Bungalow in Winona
*Prairie Island Bungalow with Water Access*
Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!
₹7,929 per night

Stay near Winona's top sights

Minnesota Marine Art Museum32 locals recommend
Bloedow's Bakery13 locals recommend
Hy-Vee5 locals recommend
Bub's Brewing Co7 locals recommend
Acoustic Cafe15 locals recommend
The Boat House Restaurant14 locals recommend

Other great holiday rentals in Winona

Flat in Winona
Oma's Treehäus & Rooftop Deck
₹10,418 per night
Home in Winona
Winona, MN- Cozy 3 bdrm bungalow with river view
₹11,251 per night
Home in Galesville
The BarnWood Company Guest House
₹11,679 per night
Loft in Arcadia
Tamarack Point Homestead
₹8,001 per night
Flat in Onalaska
Northshore Studio on Lake Onalaska
₹7,084 per night
Flat in Trempealeau
Small Town Vibes with Amazing River & Bluff Views
₹10,418 per night
Home in Winona
Spacious Retreat for 1-8 guests
₹18,752 per night
Flat in Onalaska
Lakefront Studio
₹7,917 per night
Flat in Winona
The Exchange 15 | Historic Bldg, Studio, Dwntwn
₹6,846 per night
Flat in Winona
Treetops Suite for Two @ 7th Street Retreat
₹7,084 per night
Home in Fountain City
Bluffside cottage with gorgeous river views
₹9,465 per night
Home in Winona
The Driftless House - Winona, MN
₹17,466 per night

Quick stats about holiday rentals in Winona

Total rentals

70 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

5.5T reviews

Nightly prices starting at

₹1,667 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Minnesota
  4. Winona County
  5. Winona