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Top rated Winona house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Jillissa stayed overnight with my fur babies. She kept in contact and sent pics with updates. I felt very comfortable with her in my home and will not hesitate to book with her again!”


“Booked Peyton for both house sitting and drop in visits the week of 3/22/2026. She was great with taking care of my cat Turbo and providing pictures during my vacation.”

“Jaxon recently cared for my two dogs in my home. He was positive, professional and a great communicator. This was my first experience on Rover and I could not be more pleased. I would have him care for my pets again in a heartbeat!”

“Isabelle watched our three dogs while we were away for the weekend and did a great job! Our pups loved her, especially our pup that is usually very nervous around people he doesn't know. She was quick to respond to our initial request to have her pet sit and she sent lots of updates and pictures. We will definitely be asking her to watch our pups again for upcoming trips!”


About: I have two dogs of my own, both golden doodles, who I take care of daily! I do daily feedings, walks, and brushing. I have experience in both daytime check ins and overnight stays with dogs. I am very active and enjoy taking dogs on walks, running around the backyard, or just relaxing in the house! I am flexible in the work I do and can’t wait to meet your pet:) I am a college student, so over the summer my days are free! I am available at any time needed, starting at 7am through overnight care! I care for my own pets by taking them on daily walks, creating activities that engage them, and brush their fur. I will care for clients pets in whatever ways are necessary for the specific animal!
About: We’re Pawz & Play! We offer dog & cat boarding, weekend daycare, drop in visits, dog walking, and house sitting in Winona, MN. We operate on a small-scale, only taking a maximum of 2 pups or one family’s pets at a time. Erica is an aspiring dog groomer & trainer who someday hopes to have her own facility. Ciara is working on getting her bachelors and is the primary person on drop in visits. We have two medium sized young dogs who love to play & get along great with playful pups of all ages and sizes as well as an older small dog who does great with calmer pups. All dogs are assessed for play style and comfort level before being split into play groups. One of us is home the majority of the time and we incorporate your pets into our girls’ daily routine or we can do a rotation schedule if they’re not a fan of group activities. Our fenced in back yard has a good size dog run within the fence just for pups and the rest of the yard includes the chickens & rabbits in their own runs as well as a small patio, hammocks, and garden beds. Whether in your home or ours, we are happy to serve your pets whatever food you’d like including homemade, raw, canned food, or kibble. We just ask that it be premade so we need only measure out the amount and feed your babies.
“This is the 3rd time I have used Ajia for over nite cat care and again what a great experience! Pics, communication, and house care great. Thank you Ajia, for going out of your way to make my husband and I's recent trip more pleasurable.”

“Jacque was wonderful while staying with my puppy Atlas for the weekend! She provided me with great updates and pictures. I could tell Atlas really liked her and he was the same happy, sweet pup when I returned home!”
“Laren stayed for a 3 day weekend with our 3 dogs and 2 cats. She did a fantastic job. She followed through on all our instructions and requests. She was prompt in returning messages and sent us photos too. She even made friends with our very shy cat who will normaly never even be around strangers. She's truly a "cat whisperer"! We recommend her highly!”

About: I’ve been caring for animals my whole life and have 4 years of professional experience from working at an animal sanctuary and currently a vet clinic! I am also going to school in Rochester to become a veterinary technician! Having a dog and two cats to care for of my own and currently working at a vet as a vet assistant. My days always consist of caring for animals and I wouldn’t change it for anything. At home I have another dog who gets along well with other dogs and people. I also have 2 cats but they are outdoor only and are used to dogs. I have a big house with an even bigger yard. I can take your dog on walks or hikes and they will get plenty of exercise. Inside the dog will have its own space and I can crate your dog if needed. I am willing to work with any accommodations you need for your furry friend.
About: I’ve been around dogs since I was born. I adore every dog I meet and I’ve gotten the silly name of being a dog whisper with dogs that usually don’t like people. I’m patient and caring with all dog types. Along with liking to take dogs on walks and getting their energy out! ⭐️I have flexible rates- I can also do Venmo so rover doesn’t take a percent of the money! I’m more in this to spend time with dogs! Not money! Right now I am available in the morning and weekends to keep your pups safe and cared for if there’s a trip planned! After may 15th I’ll be available almost all the time! I will make sure your pets stay on their routine while also giving them all the love! If I house sit I also will usually clean up the house a bit and spend most of the day with your pets!
About: I grew up on a farm and I have experience with multiple different breeds of animals. I take the time to listen to animals and their body language. I work part time. So i have plenty of extra time to spend and care for your fur baby. Im available Monday to Friday after 2pm and weekends! I have plent of yard space and easy access to walking tails and parks. I do have a dog friendly cat who can keep ur fur baby company
About: I have taken care of my own dog as well as taken family friends dogs on walks and runs. I am currently training for a half marathon, so if your dogs loves long runs or long walks I would love to help them get outside and exercise. I currently am working part time on top of school. Most days I can take dogs on a walk or run in the morning to later afternoon! I currently live in an apartment where pets are not allowed, so for now I will stick to taking dogs on walks and runs whether that’s around a safe neighborhood or at a park.
About: I joined Rover to help feed my love of multiple dogs! Since I travel occasionally, managing one dog full-time is enough for me. However, I grew up with 3 to 4 dogs on average. Choose me and your dog will have all the love and attention! I’m in my 30’s and work from home remotely M-F. I volunteer at multiple rescues, so have recent experience with different dog sizes and breeds. When I was younger, I use to be an AKC Junior Handler in dog shows. My personal dog experience ranges from Papillons, Lab/Golden Retriever mixes, Goldendoodles, and a Doberman. I’ve also owned multiple cats growing up, so are also available for feline drop-ins. I even have experience with tiger cubs! I spend a lot of time with my dog and will give your dog the same attention. I am available for walks, drop ins and overnights. I currently work remotely from home so have a pretty open schedule to come take care of your pup at your home or housesit during the week. I take care of your pets at your home so safety is not an issue. This gives my customers an ease of mind that their animal is in it’s normal environment.

“Abbey’s communication, flexibility & care were excellent. We arrived home to a well kept house and a very happy & healthy dog. We’re thrilled with Abbey as a sitter and are delighted to have found someone we can trust to care for our fur baby. Abbey has made it possible for us to travel worry-free.”

“Eliza was absolutely terrific. She was so patient with our senior dog (15 yrs old) Also, our new rescue (9 yrs old) we have been workibg on house training her. Eliza spent the nights here as well (which not all dog sitters will do). I would highly recommend Eliza. She was here for 7 nights 8 days. Great personality and easy to communicate with. Bonnie”


“Storm was an absolutely incredible pet sitter! She was very easy to contact and gave lots of updates while I was out of town and my dog loved her. :) He even got a handmade report card at the end of her stay! I had such peace of mind knowing he was in her care.”

Over 57 pet parents in Winona have booked house sitting
Winona pet parents share their Rover experiences
Naomi was fantastic with our boy Junior. We booked her to spend the day and night with him on our wedding day and she went above and beyond sending us so many updates and notes about how he was doing and what they were up to. We will definitely be rebooking in the future!

Skylar absolutely saved the day for me when another Rover sitter had to cancel a few hours into the first day of a three day house/dog sit. I was already hours away from home and she worked with me remotely to effect a smooth handoff. It was a huge relief after a stressful afternoon! She took great care of my two pups and kept the house tidy. She sent me photos and was good about responding when I would check in periodically. Already planning to hire her for my next trip!

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Winona is $40
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Sitters in Winona average 3 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winona on Rover as of Jun 2026 was about $40 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 169 house sitters in Winona. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 82% of Winona house sitters respond in under an hour.
House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winona.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winona house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.






