House Sitting in Winona
Find a loving house sitter to watch over your pets and your home.

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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.

“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!”


“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!”


“Ajia was great with Maverick! He was comfortable with her immediately and they had a great weekend while I was away. Definitely hope to have Ajia come hang with Mav again and would recommend her to anyone!”


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.

“Ashley was great. Very thorough and took great care of Dove. She took excellent notes to make sure Dove had everything she needed to a T. I highly recommend Ashley and would book again in the future.”


About: Although I am newer to dog sitting, I have stayed at family and friend’s homes with their dogs multiple times in the last year including following feeding schedules, walking, playing fetch, and more. I love to play fetch with dogs and sometimes end up enjoying it more than they do. I have a high energy personality that is also nurturing and sweet. I personally one day want at least one dog of my own so this is good experience in and of itself to learn about different breeds. I would love to get to know your dog :) I do work a job 8-5pm during the weekdays, but am open on the weekends and would be willing to stay the night at your home. I offer checking up on your dog during my open breaks during the day, playing fetch, walking your dog, pee breaks, and following a feeding schedule that you have. I am also open to learning new skills that you are open to teaching me and that are within your comfort.

About: I have taken care of a multitude of pets throughout my life, especially dogs of various sizes and breeds. Pets aren't just pets, they're family and I really truly resemble that through my care. I know how to care for your pets to keep them happy and healthy. I am a current college student with only a couple classes (maximum) a day, leaving me with lots of time to schedule for the rest of my day. I am easily able to frequently care for your furry friend as much as desired, and have lots of time to give them walks and belly rubs. I treat all animals that feel comfortable with lots of love and pets, and care for them like they're my own. I do not pull on the leash while walking, never punish with physical force, and treat all pets like family. I also respect everyone's homes and places of living, and will leave it just the same or better than when I came.

About: I have had a love for animals my whole life! I used to be the neighborhood dog walker and brushing service growing up! I currently have two Golden Retrievers and a Cavapoo! I also breed my Golden Retriever so we get to raise Golden puppies until they go to their forever homes! I have plenty of references available! I am at home so I have a very wide open schedule to care for your pets! I am available for you Sunday through Saturday, morning, afternoon, and night! I will have your pets safely on leashes when outdoors in my care! We will take walks for exercise! Your fur babies are allowed to free roam in my home with my other 3 dogs! (I do have a crate if needed)

About: I raised and since have consistently cared for my mom’s dog for the last 7.5 years. Additionally, friends and family have regularly asked for me to assist them with dog care. I have watched, walked, and spent the night with their pets. I have lots of energy and am capable of giving energetic dogs proper exercise through walks and/or play. I am also capable of relaxing and giving the proper care to pets that are more relaxed and need less exercise. I work from 7:30-4 every day, Monday through Friday, and am able to care for pets outside of this schedule, before or after the shift starts. I give lots of love and attention, but I do not force the dogs into uncomfortable situations. I allow them to communicate to me with their needs. I also have the capacity and am eager to play as much as the dog likes.

“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!”

About: Hi there! My name is Kali, and I’ve been an animal lover my whole life. I grew up with dogs of all sizes and personalities, and they’ve always been a big part of my family. We also had a cat in the house, so I’m comfortable around both furry friends! Spending time with dogs is something I truly enjoy, whether it’s going for walks, playing in the yard, or just relaxing together. I’m patient, responsible, and always happy to match the energy level of your pup, whether they’re playful or more laid-back. I have experience with dogs of all ages, from puppies to senior dogs and I understand the different levels of care and attention each one needs. I’d love to meet your dog and make sure they feel safe, happy, and cared for while you’re away! Now through the end of August, I’m local in Winona and work remotely most days. I commute to La Crosse only on Wednesdays (7:30 AM – 3:30 PM), so I’m very available in Winona the rest of the week. Starting in September, I’ll be commuting to La Crosse Monday through Friday, and will be available for pet care after work hours. I’m also available some weekends, and I’ll always keep my availability updated here so you know exactly when I’m free. While I won’t be caring for pets in my own home, I take pride in providing attentive, respectful care in your pet’s home where they’re most comfortable and familiar with their surroundings. I’m happy to help with feeding, walks, playtime, crating, or anything else they need within reason. Your pet’s well-being is my top priority, and I’ll treat your home and animals with care and respect!

About: I've trained service dogs and grew up with a lot of labs. I have always had a pet in my home from hamsters to horses on the ranch! Love animals from small to large. I am currently working part time with pets. I can work any day of the week including weekends! Would like to eventually make pet sitting a full time job! I have two large dogs at home that are loced in so many ways! Spoiled to the limit! The best boys I have been blessed with!

About: I’ve taken care of dogs since I was young. I have raised some of my own as well. Neighbors would have me dog sit for weeks at a time. I am currently in between jobs so my availability is open! I am willing to accommodate schedules and work around things to ensure the best quality of care! My cat is treated like a princess. She goes on walks and never is bored. I stimulate her twice a day for a minimum of 2 hours. The world is only as big as you allow your pets to see.

About: I have worked at a dog boarding facility for over two years providing high quality care for all different kinds of pups and their needs! I also have an old pup myself who is spoiled with belly rubs and treats who is currently at home with my parents while I attend college! I can accommodate to any needs you and your dog need like a specialized feeding schedule, allergies, exercise, and more! Pet care has fit into my schedule daily from working at a pet boarding facility to taking care of my own pup! I am constantly giving service to any pups that need it to keep them and myself busy! Your pets will be cared for with high quality service and love! I treat every dog like it is my own and spoil them with that they love doing! If your dog is a cuddler then I can provide cuddles and if your dog likes walking I can walk all day long!
Loving house sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Cali R.Star Sitter

“This is our 2nd time using Cali and we already have our 3rd time booked! She is professional, timely and we love her daily updates. Highly recommend!”


Isabelle K.

“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!”


Jillissa R.Star Sitter

“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!”


Ajia W.Star Sitter

“Ajia was great with Maverick! He was comfortable with her immediately and they had a great weekend while I was away. Definitely hope to have Ajia come hang with Mav again and would recommend her to anyone!”


Rebekah L.

“Great sitter. Our dogs love Rebekah already after a single overnight stay. They were well cared for.”


Skylar M.

“Skylar is an absolute blessing ! She loves and attends to all of our babies like they are her own. We couldn't ask for a better fit for all of our animals.”


Erica & Ciara M.
“Ciara did drop in visits for me when I first got my new puppy. She was great with her and the puppy had so many fewer accidents than she would have if I’d only come home on lunch! She also did a great job with the puppy on positive crate association. Now the puppy knows kennel means she goes in the crate and she has no complaints.”


Ashley D.

“Ashley was great. Very thorough and took great care of Dove. She took excellent notes to make sure Dove had everything she needed to a T. I highly recommend Ashley and would book again in the future.”


Taylor D.
About: Although I am newer to dog sitting, I have stayed at family and friend’s homes with their dogs multiple times in the last year including following feeding schedules, walking, playing fetch, and more. I love to play fetch with dogs and sometimes end up enjoying it more than they do. I have a high energy personality that is also nurturing and sweet. I personally one day want at least one dog of my own so this is good experience in and of itself to learn about different breeds. I would love to get to know your dog :) I do work a job 8-5pm during the weekdays, but am open on the weekends and would be willing to stay the night at your home. I offer checking up on your dog during my open breaks during the day, playing fetch, walking your dog, pee breaks, and following a feeding schedule that you have. I am also open to learning new skills that you are open to teaching me and that are within your comfort.


Ellery A.
“Ellery is a good friend of mine, she is very responsive and trustworthy. She is a very timely person and good at getting any tasks done on time and done well. She has many pets and cares for them all well. She has a very compassionate personality and would be a good dog walker/sitter.”


Alicia G.
About: I have had a love for animals my whole life! I used to be the neighborhood dog walker and brushing service growing up! I currently have two Golden Retrievers and a Cavapoo! I also breed my Golden Retriever so we get to raise Golden puppies until they go to their forever homes! I have plenty of references available! I am at home so I have a very wide open schedule to care for your pets! I am available for you Sunday through Saturday, morning, afternoon, and night! I will have your pets safely on leashes when outdoors in my care! We will take walks for exercise! Your fur babies are allowed to free roam in my home with my other 3 dogs! (I do have a crate if needed)


Abbey S.

“Abbey is very calm and capable. She took care of our two pups, and we were able to have a relaxing weekend away. We definitely hope to have her back again.”


Austin K.
“Austin is a very responsible and caring young man. He takes care of his animals well and makes sure they're as happy and healthy as can be. His commitment to care is unwavering.”


Olivia A.

“Cooper looked so happy when we got home!”


Jacque K.
“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!”


Kalista Y.
“I highly recommend Kali as a pet sitter, she loves all animals especially dogs! She has been nothing but amazing with my dog since he was a puppy until 3 years old now. She truly loves him like her own and would treat all pets this way. I know my dog is in great hands when Kali watches him, she is a very reliable and loving caregiver.”


Elijah E.
About: I've trained service dogs and grew up with a lot of labs. I have always had a pet in my home from hamsters to horses on the ranch! Love animals from small to large. I am currently working part time with pets. I can work any day of the week including weekends! Would like to eventually make pet sitting a full time job! I have two large dogs at home that are loced in so many ways! Spoiled to the limit! The best boys I have been blessed with!


Madison B.
“Madison (Maddy) is a responsible person who will have nothing but the pets best interest and safety in mind when caring for them. She loves animals and grew up caring for them. She will do a great job.”


Erin G.
“Erin has a heart of gold. She has gone above and beyond in caring for our precious family pets. She lovingly cared for Lucky, our cat who is still happy and healthy, and Rusch, our beloved dog who has since passed, while my husband was hospitalized. Although we missed them dearly, we knew they were in the best hands. Erin treats every pet as if they were her own, showering them with love, ensuring they are well-fed, and attentively meeting their every need. Her compassion, reliability, and dedication would make her a wonderful addition to your team!”




Michelle N.

“Michelle took great care of our two dogs and one cat while we were away. Our dogs felt comfortable around her right away. Michelle was flexible and communicative.”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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 Aug 2025 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 Aug 2025, there are 51 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, 86% 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.
