Family-friendly holiday rentals in Winona

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.

*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!

The Cottage at The Healing Refuge

Welcome to The Healing Refuge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless area! Relax outside on the deck, swing in a hammock among the trees, or walk through our beautiful cover crop fields. This is a working farm & depending on the season, you are welcome to help collect eggs, chat with the horses, observe the numerous farm animals, or learn about regenerative farming. We want your experience at our farm to be relaxing and refreshing!

~ Third Street Suites ~ #3

This beautiful 2nd story loft 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, restaurants, bars, brewery, 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!

A cozy shed house located in the rolling hills.

A cozy shed house located in the hills of Coral City, WI. This Shed house includes a private deck, cozy living room, full kitchen, 1 bedroom with queen bed, 1 bathroom with shower and extra air mattresses, sheets, & pillows for guests. It is surrounded by nature but near to the city. We are also located close to many wedding venues. The Shed House is a separate building, but located on the same property as the owner's home. During the winter months, 4-wheel drive is necessary.

Driftless Farm Getaway

Unplug and see the stars - Treat yourself to a low-tech escape into nature where you can relish the peace of a hardwood forest, soak in outstanding views, engage with fun farm animals and just relax. This private cabin is located on the edge of our pasture-based farm - we have 160 acres of forest, pastures, bluffs, and cliffs to explore. Just off the farm, this area is home to world-class trout fishing, the Root River State Trail, Amish shops, and so many hidden gems!

Pleasant Pastures, Dakota MN

Get cozy and settle into this rustic space. Spend some time at our farm in SE MN enjoy watching the cattle graze, beautiful Ridge top sunrises & sunsets and enjoy an outdoor meal with one of our delectable steaks! This is a true working farm, our family operates 600 acres of crop land along with 200 head beef cattle, go ahead and check out the cattle and pigs, or take a hike through our 3 miles of trails through our woodland!!

Garden Glamping @ Whispering Winds

Immerse yourself in nature & experience the magic of the lush gardens, free-roaming bunnies, fairy walkway, stargazing area w/ telescope, meditating in the Soul Garden, fishing in the fully stocked trout stream and more. 5 minute walk to City Park w/ frisbee golf, less than 0.5 miles to local restaurants & shops. Come relax, rejuvenate, and live out your best life at Whispering Winds Micro Retreat! (420 & pet friendly)

Potluck String Lodge (PSL)

Potluck String Lodge (PSL) is situated within Prairie Island Campground along the Mississippi River. With cottony sheets, coffee & towels, paddle sport equipment & bikes, and an outdoor fire ring, you can simply show-up, relax, reconnect, and recreate. This tiny house tells a story about the Boats and Bluegrass music festival and one of the campground picking circles hosted by the Potluck String Band.