Holiday rentals in Winona

Dreamy Waterfront Home - Hot Tub, Lake Pepin View!

The Dockside is the premier waterfront vacation rental and event space in Pepin. Right on the lake with expansive views of the marina and river bluffs, it's the perfect place to stay, whether you're here for a wedding, family trip, or any other reason! Our two units -- the A-Frame Cabin and the Marina Bungalow -- combine to make one large 2600 sq ft, 4-bedroom, two-kitchen property. Enjoy the outdoor hot tub, too! Each unit can also be rented separately -- see my Host Profile for the listings!

Country Chic, Hovde Home at Labrador Farm

Come enjoy the peaceful surroundings of this rustic destination. Surrounded by nature and coupled with many modern luxuries. Breathtaking views from the porches. Cozy up at the fire pit to stargaze or roast some marshmallows. Offload horses, paddock available with water (4-6 with signed waiver). Bring your furry-faced family members ! Do not leave on the property unattended please. Pets are welcome but must be supervised. There is a fee PER pet but all Dogs welcome! Enjoy our hidden gem!

Charming 3 bed/3bath renovated cabin on Lake Pepin

This is the perfect quiet getaway! High end renovation with 100 ft of private beach on breath-taking Lake Pepin. Revel in this home’s private owner’s suite, sunny open floor plan, wood fireplace, expansive deck, and incredible lake views. *Per local ordinance: 6 guests max over 5yrs old, no parties/events. *No more than 3 vehicles allowed. *No more than 3 additional guests allowed *No recreational vehicles, campers, or tent camping allowed. *Quiet outdoor hours from 9pm-9am. *No fireworks

"Amazing Views" of Lake Pepin in Lake City

Amazing Views is Lake City's "Premiere" Vacation Rental! From its perfect location, to the absolutely Amazing Views and lake cottage feel, you will love this home! Enjoy Adirondack chairs under the pergola in the summer to watch the eagles, pelicans and sailboats. Cuddle up by the red brick, gas fireplace in the living room in the winter. A perfect home for every season. Just 2 blocks away from Ohuta Beach and the Marina. Bring your friends and family to this "Amazing" home!

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!

Bayfront Chalet on Richmond Bay

Waterfront Property- 3 bedrooms, 2 full bath home - You will be amazed at the views from this extravagant French Island house on Richmond Bay. It features JennAir stainless steel appliances including dishwasher, laundry, central air, free Wifi, large deck and use of a nice sized dock for boating, kayaking or jet skiing. These items (boat,kayak,water crafts)are not included with . Airbnb. Fireplace is for aesthetics. Less than a 10 minute drive to the La Crosse Center.

Two Bedroom upstairs airy modern apartment

This upper level apartment has beautiful natural light, a combined living/dining space, two well-appointed bedrooms with built-in desks, a fully furnished vintage kitchen, a full bath, and a private deck. It is available at a discounted price for longer stays. This apartment is part of three apartments in an older home but has a private indoor and outdoor access point. Two queen beds, one single bed and one sleeper sofa. Reserved parking by the entry door.

Luxury Retreat Nestled in Bluffs -10 Mins Downtown

Newly renovated luxury home nestled in the bluffs of scenic La Crosse. Conveniently located 10 minutes to downtown La Crosse. Enjoy the vaulted wood beam ceilings and stunning views. Cozy up in the living room by the fireplace and revel at beauty and seclusion of the nature that surrounds you. Every detail has been thoughtfully curated to ensure comfort, relaxation, and fun. Expansive outdoor spaces.

Backwater hideaway. Big house with water access.

Lovely house with tons of space. Located on Brice Prairie, this house sits on a back stream of the mighty Mississippi/lake Onalaska. Accessible by flat bottom boat, kayak or similar. Not a great swimming spot with being often a bit weedy. Great ice fishing just down a bit and a large fenced in back yard. House has two kitchens, formal dining, large deck, rec area with kids items.