Waterfront holiday rentals in Winona County

River House

Perfect for those seeking tranquility & natural beauty. A peaceful haven offering an ideal setting to relax, recharge, & reconnect while enjoying modern comforts. Start your day with a cup of coffee on the spacious deck as the sun rises over the majestic Mississippi. Breathtaking views make every morning unforgettable. Located just outside Great River Bluffs State Park, miles of scenic hiking / cross country trails that wind through forests & dramatic bluffs view over the Mississippi valley.

The White House

Located in the center of town about 10 minutes from Winona. Centrally located and steps from the Mississippi River providing captivating views of the area and surrounding bluffs. 5 bars/restaurants and a winery located within 1 block and plenty of other adventures nearby inc fishing, hiking boating and more! Property has 2 workstations with a total of 2 monitors (32" and 24") making it the ideal remote worker location in a small town. Feel free to reach out for other suggestions!

Spacious home w/hot tub and river views!

Welcome Riverfront Retreat on the Mississippi This beautifully renovated 2,800-square-foot home offers the perfect blend of comfort, nature, and adventure. With a spacious, fenced-in backyard, a private dock, and a boat garage, it's a dream destination for fishing enthusiasts and water lovers alike. • Relax year-round in the backyard hot tub • Gather around the fire pit on the scenic point, surrounded by water • Watch eagles soar and ducks paddle—wildlife is abundant and awe-inspiring

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.

Port 19

This amazing location is perfect for your getaway! The only home in Winona on the main channel of the Mississippi River! With it's open concept, it features a sunken living room, full kitchen, work space area, W/D, private deck, grill, huge yard, fire pit, and all of this is just waiting for YOU! Trailering your boat? Not a problem! (Must be approved). Boat ramps for launching near by! And walking distance to down town and your favorite watering hole! Come relax and enjoy!

Northshore Studio on Lake Onalaska

Lakefront studio where retro and rustic charm meets modern convenience. Studio offers everything you need for a relaxing and enjoyable stay including a queen-sized bed, a living area with a Roku TV, a full kitchen and a bathroom with a step in shower. The lakefront screen porch provides the perfect spot to enjoy your morning coffee or unwind with a good book. Two sit on top kayaks are included. Bikes are available and hiking and biking trails are just across the street.

Beautiful Cozy Lake House on 2 & 1/2 acres!

Nestled on 2.5 acres of woods, lawn, and lake shore, our charming lake house offers a peaceful retreat in Galesville, Wisconsin. Immerse yourself in the beauty of the surrounding area, just a 10-minute drive from Trempealeau, the Mississippi River, and Perrot State Park. Winona, Minnesota, and La Crosse, Wisconsin, are just a 20-minute drive away. A scenic drive along the Great River Road is a must, allowing you to admire the river’s splendor and the majestic bluffs.

Dragonfly Loft, hot tub, river views

Welcome to our cozy retreat in Fountain City, Wisconsin, where the serene beauty of nature meets the charm of small-town living. The Mississippi River is your backyard! Our inviting 2-bedroom, 1.5-bathroom vacation rental comfortably accommodates up to 4 guests and warmly welcomes furry friends, making it the perfect getaway for families and outdoor enthusiasts alike. Train track, firepit, hot tub, oh my! Ask us about our weekly specials!

Backwaters lodge

This cabin sits overlooking a beautiful view of the water where you will see all types of wildlife. The eagles sit in the giant oak trees just off the porch. Walk down to the dock and drop a line in for fishing. .The state bike/snowmobile/hiking trail is within 3 minutes. The boat landing is 1 mile away. You have your own private dock. We also just added a hatchet throwing target We charge a 25.00 per visit pet fee.

The BRD Nest Mississippi River Home with Views

Breathtaking views of the Mississippi River & Minnesota Bluffs from this spacious 2700sq ft home! A mile to boat launching and .5 mile to Perrot State Park for outdoor adventures! Relax and enjoy the breeze from the River on the balcony. Enjoy the deck and grill your dinner while you watch the sunset up the River for postcard like pictures! Wildlife and woods surrounds the back of the house for a truly peaceful stay.

Waterfront | HOT TUB | Sleeps 15

Experience the ultimate riverfront getaway in this spacious 3,700 sq ft home on a fenced half-acre with a large dock, hot tub, pool table, movie theater, ping pong, shuffleboard, popcorn station, yard games, and plenty of seating. Relax in the sunroom, by the indoor fireplace, on the dock, or in the hot tub. Perfect for family gatherings, weddings, bachelor/bachelorette parties, or an unforgettable friends’ retreat!

Cottage House on Lake Onalaska

This Cottage Lake Home is located on the bank of Lake Onalaska in Brice Prairie, WI. 3 bedrooms main floor, 1 kids setup in basement, a full bathroom, a full kitchen, a patio/fire area, make this a perfect place to relax and enjoy the area with your group. Perfect for families, solo travelers, or small groups looking to get out on the water! (we have boats available to rent pontoon boats and flat bottom boats)