Vacation rentals in Stockton

✨Vintage Lustron Home✨

Enjoy a stay in this vintage Lustron Home. It is a unique home. It has two bedrooms, and a sofa sleeper in the living room. The master bedroom has a queen size bed. The second bedroom has two twin beds. This home offers a washer and dryer for your convenience. It has a large fenced yard to enjoy during your stay. Off street parking and Wi-Fi included. This home is in a very peaceful neighborhood. Located close to Winona State University and St. Mary's University. There are State Parks close also

Carol's Cottage

Carol's Cottage is truly a one-of-a-kind property! Originally built in the 1850s you will find the majority of the home still full of all it’s original charm! The cottage is situated on a beautifully manicured yard that is extremely spacious. Enjoy exploring the creek beds for unique gems and stones. The home is cozy and quaint but still spacious. Large living room. All the beds are located in one central area in the loft, along with a toy room and a built in gate at the top of the loft stairs.

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

*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!

Quiet Cottage in the Valley with Sauna

Nestled in the bluffs of Winona, Minnesota, The Driftless Retreat is a cottage in the valley just one mile from Saint Mary's University and a 10 minute drive to downtown Winona and the Mississippi River. The cottage features a private front and back entrance, large backyard, and woodburning fireplace. Our hope is that The Driftless Retreat is just that, a retreat away from the every day. We believe that every detail matters and take pride in making your time here relaxing and enjoyable.

River Road Abode: breathtaking river views

Entire 2 bedroom home with amazing views of the Mississippi from every room in the house. 3 unique decks to watch birds, barges, boats, bluffs and trains. Out front you can wave at people passing by on the Great River Road. Located near WI and MN state parks, wineries, breweries, and restaurants. Adventure outdoors or stay in and watch all the Mississippi has to offer from the private patio and decks. Trains pass by property day & night. Home is well insulated & ear plugs are provided.

The Guest House

Modern one-bedroom home— bright, fresh, and fully updated! This beautifully designed space seamlessly blends modern comfort with calming touches, making it perfect for relaxing after a long day of work, travel, or adventure. The home is just minutes from Winona’s lakes, trails, dining, and downtown attractions. Whether you’re here for outdoor adventure, a weekend getaway, or a comfortable remote-work base, this space offers everything you need for a smooth and enjoyable stay.

Bluffside cottage with gorgeous river views

Hill Street House is the quintessential river-town residence, located within walking distance of Fountain City's quaint downtown, legendary pubs, and riverfront, but just far enough from the highway and trains to still get a good night's sleep. Perched snuggly on the bluffside overlooking the Mississippi River, you'll see an ever-changing panorama of river boats, barges, and birds in flight against a backdrop of Minnesota bluffs in the distance and a jumble of rooftops below.

Lady Liberty - bikes & grill available as add-ons!

Welcome to Lady Liberty, our cozy retreat in downtown Winona, MN! Our recently restored home blends historic charm with modern comforts, perfect for a family or group of up to four. With one bedroom, one bathroom, and a spacious living area, it’s designed for relaxation and connection. Just blocks from local cafes, shops, and the scenic Mississippi River, you’ll find endless opportunities to explore. Book now for a memorable stay—we can’t wait to host you! – Jaime and Allison

August Ridge / HOT TUB / Sleeps 4

Welcome to August Ridge, a thoughtfully designed blufftop retreat where modern comfort meets unforgettable views. Perched high above the Mississippi River Valley, this two-bedroom, 1.5-bath getaway offers the perfect place to relax, reconnect, and soak in the beauty of Wisconsin’s Driftless Region. Hosted by Rentals Justin Time Hot tub is available year round!

Warbler Lodge

Warbler Lodge is situated within Prairie Island Campground along the backwaters of 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 flora and fauna of the Prairie Island park area.

Tamarack Point Homestead

Tamarack Point Homestead is located between Arcadia, WI and Centerville, WI in the beautiful valley of Tamarack. This scenic 150 year old homestead has an outbuilding loft that allows you to enjoy the country lifestyle and experience the best that Trempealeau County has to offer. Certified to operate by the Trempealeau County Health Department.