
Pet-friendly holiday rentals in Winona
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Top-rated pet-friendly home rentals in Winona
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Popular amenities for Winona pet-friendly home rentals
Pet-friendly house rentals

Beautiful Craftsman Bungalow - Centrally located!
Absolutely amazing for my family of 5!!! Each of my kids had their own room with plenty of space to hang out. Beautiful little backyard with a firepit that we sat around in the quiet evenings. We were able to walk around the neighborhood and felt completely at ease. It's also super close to great hiking trails and a cheap Uber to bars and restaurants. Highly recommend!!!

The River Shack
This was our second time at the River Shack and it didn’t disappoint. Theresa is very friendly and responsive! I will recommend her place to anyone staying in the area. The river views and the garage are perfect!

The Driftless House - Winona, MN
The house was above what was described in words and pictures Celeste was great to work with. Very responsive and flexible Would recommend this property to anyone.

Lovely bungalow!
Manette’s place was easy to access and upon entry could tell it was taken care of. We all slept great, very comfortable. Everything we needed was there, host really had thought about what a traveler might have forgotten.

A Stone's Throw Bungalow
Megan was such a friendly and responsive host, and her home was the perfect place for my kiddos and me to stay when we were visiting family in Winona! The home has a beautiful, big fenced-in yard with plenty of grass to play in, all of the amenities that we needed, including smart TVs, all of the kitchen appliances we wanted, games and puzzles, and a nice long driveway. It’d also located just across the street from the lake, which is really convenient and so lovely! All of Megan’s amazing photography lining the walls is an added bonus :) We can’t wait to stay here again the next time we’re in town. Thanks, Megan, for giving my crew such a cozy and comfortable place to land!

Little House on the Prairie
We enjoyed the peaceful area, kayaking and walking on Brice prairie.

Historic Carter House-Rivertown Romance-Licensed!
Check in was easy and Signe was very communicative. We enjoyed drinking our coffee in the big yard and learning about the history of the place. We had everything we needed including tips on exploring the area. We recommend Grandad Bluff and the Pizza Cruise. Great town if you appreciate dive bars and Mac n cheese.

Nostalgic Retro Cottage-Faye's Place-Fully Fenced
What a sweet place! It was full of character and charm!
Pet-friendly home rentals with a pool

3 Bedroom home (sleeps 8)
We had a great time and really enjoyed the house! It’s centrally located, yet quiet at night, and the neighbors we ran into were very friendly. Our kids loved the heated pool (and the amazing pool toys!), and it was great being so close to the lake - each morning we walked the path/sidewalk to spot eagles and other wildlife. One night, we built a bonfire in the solo stove - super fun. Beau was also very communicative and responsive. Definitely a trip to remember!

2 Bedroom Condo - Sleeps 6 (upper level)
Great visit to a great little City. Pool was open and clean - which the kids loved. Felt nice and clean and newly remodeled.

3 Bedroom Condo - Sleeps 6 (upper level)
Great place and beautiful view of the lake!

Secluded home w/pool, hot tub, cold plunge & sauna
Perfect home for a larger family or group! We really enjoyed our time at Mindy’s home. There was plenty of space for everyone and the pool and hot tub were bonuses! We were in town for a wedding and Mindy was very flexible with check-in and very responsive and kind. Beautiful location with a ballpark right across the street. Highly recommended, Thank you!
Private, pet-friendly home rentals

R & K Cozy Cabin
Cute little Cabin. Perfect little getaway out in the woods.

Cozy Log Cabin
Enjoyed our stay. We visited quite a few Amish businesses and their produce auction. The beds were comfortable and the birds were amazing. Loved sitting on the porch in the morning listening to the birds. Also had a doe and fawn come walking right by. We had almost perfect weather so were able to have the windows open. Nice hot shower and plenty of space. I preferred the outhouse over the incinerator toilet but that was just my preference. We did have rain one morning and couldn't cook outside. A hot plate or electric griddle would be a great addition. Other than that the stay was great. We would definitely stay again. Check in was easy and a nice note with local suggestions was so nice. We did travel to Fennimore and I would recommend the train museum if you are looking for things to do.

Outsider's Rustic Retreat
Excellent. Love this picturesque coulee, and the barn is always a hit. Perfect crash pad for us after days spent exploring trout streams.

b3 Couples Therapy Yacht
The houseboat was a unique and fun variation on vacation stays. It was a busy marina but quiet by 9:00 so no problems with noise. Several nearby restaurants to choose from or could cook/grill on the boat. I communicated with Greg via text, he was very willing to help but no issues so no need for further communication. I would highly recommend this location.

Cabin Retreat, Fireplace + Firepit, Eco-Friendly
We had a wonderful stay! The house was cute, cozy, and incredibly relaxing, exactly what we needed for a peaceful getaway. Everything was clean, comfortable, and thoughtfully set up. We’d definitely come back!

Med Park House
It was perfect for what we needed. Glen was very accommodating and helpful in his communication. We would stay there again when we ever back in the area.

Treehouse Cabin in the Bluff Woodlands North
Absolutely incredible place for a peaceful getaway not far from Rochester. The shared bathhouse was very clean and well-stocked and the lighting meant that even at night it was not bad to walk to. Chelsi was very responsive and helpful, we decided to add a night at the last minute because once we arrived we knew we wouldn't be able to leave too quickly and Chelsi was flexible and communicative. We will be back!

Spacious Trempealeau Retreat
A quiet getaway for our family to get together for my parent's 60th Anniversary. Plenty of room for us to sit outside and enjoy quiet conversation. Shaina was quick to respond to my questions.
Quick stats about holiday rentals that are pet-friendly in Winona
Total rentals
10 properties
Nightly prices starting at
$116 NZD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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