Cabin vacation rentals in Winona

Perched Above Pepin- hot tub, panoramic lake view!

Charming cabin perched on a hill w/ stunning views of Lake Pepin.Enjoy a cozy atmosphere w/ a fireplace, modern amenities, & sunroom w/ breathtaking lake vistas. Watch eagles soar and barges pass by, while listening to the sound of trains rolling by along the river.Located near hiking trails, water activities, local wineries, and breweries, this cabin is perfect for outdoor adventures.With easy access to both Lake City and Wabasha, it’s an ideal getaway, blending comfort, nature, and attractions

Location · Family · Accuracy

Luxury Cabin Retreat | Hot Tub + Bluff Views

Escape to a secluded modern cabin in Winona County. This 2BR, 2BA luxury tiny home offers bluff and farmland views, an 800-sq-ft wraparound deck, 5-6 person hot tub, smokeless fire pit, and pergola seating under the stars. Inside: quartz counters, high-end appliances, fiber WiFi, and big windows for stargazing. Dog-friendly, available, and only 20–25 min from Winona & La Crosse. Perfect for a romantic getaway, family retreat, glamping, or remote work. Your private Minnesota cabin rental awaits.

Family · Location · Bathroom

The Lodge Modern Cabin w/ Hot Tub Hiking Camping

Welcome to the Lodge, our modern cabin in Minnesota’s picturesque Driftless Region. A place to slow down, connect and immerse yourself in nature. Open layout features king sized Murphy bed in main area with additional beds in the lofted space (stair-ladder). Tent/RV sites avail (inquire for rates). 47 acres with hiking trails along limestone bluffs, spring fed trout stream and hot tub soaks under starry skies. Nearby towns Spring Grove and Houston (17 mi) for food, brewery, bike trail and more.

Location · Family · Bathroom

Esther’s River Cottage

Nestled in the bluffs overlooking the Mississippi River enjoy Esther’s cottage. Relax, regroup, reset …. watch the Eagles, take in the Bluffs, enjoy boats, and barges make their way up and down the river or catch the Mississippi Queen in all her glory. 2 private bedrooms with queen beds, and a queen size pull out in the living room . 2 full bathrooms - one on each level. Fully equipped kitchen with everything you need to enjoy your stay. The 49 steps to the top are well worth the climb!

Family · Location · Cleanliness

Rustic River Cabin

Enjoy the rustic charm of this quaint, simple cabin. A safe and short walk to the river and shared boat dock. On a quiet dead end road. Outdoor firepit with wood supplied. Cabin details: Family-friendly space. Stocked kitchen with coffee bar items. Full bathroom with tub, 1 bedroom, open concept dining/living area. Living area equipped with a full/twin bunk bed. Stoddard: Rocky's Supper Club (Wed-Sat), Thursty Turtle Bar and Kwik Trip. Public boat ramp and park just down the road.

Family · Location · Pets

Charming Cabin with Hot Tub & Fire Pit

Experience historic charm & luxury at The Paige, an updated 103-yr-old cabin in Pepin, WI. Enjoy a quiet neighborhood just a 10-min walk (0.5 mi) to Villa Bellezza Winery & Lake Pepin marina. Perfect for wedding guests, wine tours, or family trips with your pup! This dog- & family-friendly retreat offers premium amenities like a brand-new 6-person hot tub, firepit, & cozy fireplace. Walk to top local dining or take a short drive to Stockholm. Book your worry-free Pepin getaway today!

Location · Family · Laundry

Creekside Cabin

Looking for a getaway? Come to the Creekside cabin just outside city limits to test out "Tiny House Living"! All the amenities of home only smaller. This is a great place! Sit by the creek and listen to the water run or cozy up to the "Tiny" wood burning fireplace to get away from it all. Situated right on the Minnesota State Snowmobile trails. Trails also great for walking/4 wheeling/biking. Please note: you are not by yourself. We live on the property Pets not allowed.

Location · Value · Condition

The Hideaway

The Hideaway is a serene and stylish place to stay. Located on 10+ acres it’s perfect for group trips, relaxing getaways, hiking the bluffs and memorable events! It is tucked peacefully in the valley along the Mississippi River. While just a few miles from the historic town of Fountain City, Wisconsin and 15 minutes from the city of Winona, Minnesota; you’ll get to enjoy the solidarity of nature while still having the convenience of a town close by. Come hide away with us!

Location · Family · Check-in

The Valley

*NEW Set on 200 acres of hiking trails and surrounded by a trout stream, this 6,000 square foot house built in 2001 by the Amish in traditional barn-raising style is astonishing. A family- owned property since the 1890s, all of the wood for the house is from the property. This breathtaking home has 4 bedrooms, 4 bathrooms, a bar, a pool table and all of the space a family needs. Open ceilings and breathtaking views make for a wonderful time. Near Root River Biking Trail.

Value · Family · Cleanliness

Living Waters Cabin Getaway

Stunning 92 acre property. Fishing, swimming, hiking, biking, birding, campfires all in an atmosphere of the great outdoors. Spacious bedroom overlooks acres of wooded scenery and landscapes of the rolling hills of Western Wisconsin. Owners home is located approx. 200 ft from cabin. A 2.5 car garage separates buildings. Second Airbnb is located approximately 200 feet from Cabin however no shared areas and completely private and separate from each other.

Value · Location · View

The Main Stay on the Bluff

The Main Stay on the Bluff is a spacious 3,000 sq ft home with four bedrooms and two bathrooms, thoughtfully designed to accommodate a wide range of guests. The main floor is fully handicap accessible and opens to an outdoor patio with seating and a fire pit. As part of Samakya Cabins, one of two private retreats set on 65 secluded acres, the property offers incredible bluff views, peaceful surroundings, and a truly special escape immersed in nature.

Value · Location · Sleep quality

A-Frame Wellness Retreat | Pool• Hot Tub• Full Gym

Secluded A-frame cabin in the trees, cozy vibes with a full wellness setup for a reset. Morning coffee on the expansive deck, afternoons by the private pool (open June 1–Sept 1), evenings in the hot tub under the stars. Indoor fitness area: squat rack, dumbbells, rowing machine, yoga mats + open floor. Perfect for reset weekends, group getaways, or extended stays. POOLS OPEN JUNE-SEPTEMBER 1

Family · Location · Pool