Photo by Kirsten

Search Vacation Homes in Winona

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 90 Vacation Homes in Winona with updated reviews, rates, and availability.

Bayfront Cottage is a 3 bedroom house on Richmond Bay.

8.4 out of 10, Very Good, (26)
"We were up in the are for Oktoberfest Race Weekend at Lacrosse Fairgrounds Speedway. Property had everything you needed, as we were not there a ton. Just sleeping and showers. Would be a great place during the summer, with a riverfront back yard, and plenty of space to hang out and have a fire, etc."
Bayfront Cottage is a 3 bedroom house on Richmond Bay.

Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

10.0 out of 10, Exceptional, (148)
"This is our 3rd time staying here. It's a great spot to come down to see our grown kid and have everyone around. Enough to do in the house to not get bored if the weather is bad. Will be back as always. "
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included

10.0 out of 10, Exceptional, (25)
"To attend my son's commencement ceremony, we made the trip to La Crosse. We had originally planned to stay at one of the hotels, but we were overjoyed to find this beautiful house. It was a pleasure working with Beth. The house was simply wonderful. We had no idea what to anticipate, but wow, this was far more than any of the rentals I've stayed in. It is amazing how much attention to detail was put into making accommodations and providing all the extras. The house was holiday-decorated and...
The price is SAR 586
SAR 1,503 total
includes taxes & fees
20 Jan - 21 January 2025
Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included

Enjoy this newly remodeled house located on Lake Onalaska.

10.0 out of 10, Exceptional, (111)
"The Tempur-Pedic mattress was awesome. Two sunrises were beautiful. We didn't spend a lot of time in the house, but everything worked out well for our family and our dog. We appreciate the property being pet friendly."
Enjoy this newly remodeled house located on Lake Onalaska.

Riverfront Twin Home

10.0 out of 10, Exceptional, (18)
"The place was very clean and conveniently located to downtown. "
The price is SAR 563
SAR 1,236 total
includes taxes & fees
24 Dec - 25 Dec
Riverfront Twin Home

Family friendly in the peaceful heart of town

10.0 out of 10, Exceptional, (88)
"Beautiful house, close to the lake. Had everything you could need."
Family friendly in the peaceful heart of town

Comfy Cottage

10.0 out of 10, Exceptional, (26)
"Very clean, very new feeling, very nice place. Will be staying here again!"
Comfy Cottage

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

10.0 out of 10, Exceptional, (12)
"What a wonderful home for us to bring are adult children together at for a weekend in LaCrosse. The bedrooms and bathrooms are spacious. The kitchen if excellent for making a family meal. The piano was an added surprise! Thanks Matt! We hope to be back!"
The price is SAR 733
SAR 950 total
includes taxes & fees
1 Jan - 2 January 2025
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

River Front Property

10.0 out of 10, Exceptional, (81)
"We enjoyed our stay and everything was as expected and described. Will stay again. "
River Front Property

The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!

9.6 out of 10, Exceptional, (81)
"Just as described with great communication from host."
The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

9.8 out of 10, Exceptional, (27)
"This was a great vacation. It was very close to town and there was a ton of things to do around the area. We had a nice time around the pool and the hot tub was great way to unwind at the end of the day to. The owners were always quick to respond if we had any questions about the house. I would definitely recommend staying here."
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

“The Cabin” on French Island

9.0 out of 10, Wonderful, (19)
"It was nice. Cozy"
“The Cabin” on French Island

The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

10.0 out of 10, Exceptional, (41)
"View and spacious rooms and bedrooms! Every couple loved having a bathroom, with family it was fine using the 5th bathroom in another’s bedroom which had the 5th bathroom. Loved the balcony around most of the house. Sister in law locked us out of the house but management was able to solve the issue immediately, what a lifesaver to get a tired family after a wedding into the house. Wish we had more time there to be with bothers and sisters. "
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

10.0 out of 10, Exceptional, (125)
"Checking in and out was fast and easy! Clean and very well stocked! Owner commented well and timely. Bed was extremely comfortable! Convenient location!"
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

'RiverSong' Waterfront La Crosse Home w/ Dock

10.0 out of 10, Exceptional, (74)
"Beautiful home with amazing amenities! The owners were so friendly and accommodating. My family had a wonderful time here while visiting our son at UW La Crosse. "
'RiverSong' Waterfront La Crosse Home w/ Dock

Country Charm Over River Valley And Horse Farm

10.0 out of 10, Exceptional, (34)
"This place is beautiful - home as well as surrounding countryside. We had lovely views and places to walk. The house was clean, comfortable and well equipped… and the hosts were attentive and pleasantly communicative. Addressed any questions we had. We couldn’t have asked for a better place and highly recommend it! "
Country Charm Over River Valley And Horse Farm

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (118)
"This property is amazing! By far the best VRBO property I have had the pleasure to stay."
The price is SAR 1,315
SAR 2,073 total
includes taxes & fees
6 Jan - 7 January 2025
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Deluxe Double Room Non-Smoking

2.0 out of 10, (1)
"This place is truly scary. We didn’t even get to stay here because of some “glitch” that they didn’t have our reservation in the system. But from the moment we drove into the lot it was obvious this place was super sketchy. Run down appearance from the outside. Wretched odor as you walk in the door. People there who didn’t seem to care at all about what was going on. "
The price is SAR 297
SAR 411 total
includes taxes & fees
24 Dec - 25 Dec
Deluxe Double Room Non-Smoking

A-frame home on Trout Stream

10.0 out of 10, Exceptional, (2)
"We met in La Crosse with our adult children and their families for Thanksgiving. We were so happy to have Dan's A Frame had availability!! He was excellent at communication, his entire home was clean and inviting! Sometime A Frames can be cold, but this home was toasty warm and even the 2 year old stayed warm all night!! Plenty of dishes, and cooking utensils to do a full Thanksgiving dinner!! We hope to come back in the summer and do some trout fishing!!! We will be back!"
A-frame home on Trout Stream

Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater

2.0 star property
10.0 out of 10, Exceptional, (4)
"Our family enjoyed our stay! The home is very clean and comfortable. We enjoyed sitting by the fire upstairs. The guys loved watching football games on the big screen in the game room/basement downstairs. Our 13 year old loved fishing and caught his first catfish, amongst other fish, from the mighty Mississippi. We have booked this home twice and hope it is available the next time we visit. Don’t hesitate to book this home! "
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Winona
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winona

Family friendly in the peaceful heart of town

10.0 out of 10, Exceptional, (88)
"Beautiful house, close to the lake. Had everything you could need."
Family friendly in the peaceful heart of town

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (118)
"This property is amazing! By far the best VRBO property I have had the pleasure to stay."
The price is SAR 1,315
SAR 2,073 total
includes taxes & fees
6 Jan - 7 January 2025
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Creekside Cabin Getaway

9.4 out of 10, Exceptional, (104)
"Weather was better than good for autumn in Minnesota, lots of trails to walk, only disappointment was the main reason we went down, to check out the Maritime Art Museum, not impressed."
Creekside Cabin Getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.