Dog Sitting Winona
Book a Winona dog sitter to watch your dog in your sitter’s home or yours.

Over 2 pet parents in Winona have booked dog sitting
Winona, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“This is the second time I have had a chance to have Kenra watch my two very skittish kitties. This time, as the time before, was an excellent experience. Even though they didn't come out from their hiding places, Kendra handled it well and took great care of them! I very much appreciate her patience and caring attitude!”

“Genesis was a great pet sitter, taking wonderful care of both of our cats. She arrived on time and took care of all requested items. We will definitely be using her again! She's also great about sending videos and pictures and leaving a Rover card each day. Highly recommend.”

About: I focus on making dogs feel safe, comfortable, and genuinely cared for while their owners are away. Whether I’m providing drop-in visits, walks, or house sitting, I stick closely to each dog’s normal routine. This can include walks, playtime, feeding schedules, potty breaks, cuddle time, and simply keeping them company so they feel relaxed and secure in their own environment. I’m dependable, attentive, and provide regular updates and photos so you can feel confident knowing your pet is happy and well cared for. As a proud dog mom to a husky, caring for dogs is already a big part of my daily life. Beyond caring for my own dog, I’ve helped family and friends by looking after their pets while they travel or have busy schedules. These experiences have taught me how important consistency, patience, and trust are when caring for someone else’s furry family member. I work full-time as a manager, but pet care fits naturally into my routine. I carefully manage my schedule to ensure pets receive the attention, exercise, and companionship they need during my visits. My goal is to provide reliable, loving care and give pet parents peace of mind while they’re away. Because I have a dog at home, I do not offer boarding services. While my husky is friendly, I believe being realistic about the services I can provide helps ensure the best experience and safety for every pet in my care. Dog mom to a husky, caring for dogs is already part of my routine — through walks, care, and helping my family pets feel loved Because of the dog I have at home, I do not offer the boarding service. Although friendly, it just is not a realistic service for me.
About: Hi! I’m Stephanie. I’m currently home from college for the summer and have a flexible schedule, so I’d love to spend my time caring for your pets! I’ve had dogs my whole life and have experience pet sitting through Rover as well as for friends, family, and neighbors. I’ve done drop-in visits, dog walking, feeding, and overnight house sitting. I genuinely love animals and enjoy getting to know each pet’s personality. I’m reliable, responsible, and will treat your pets like they’re my own, making sure they feel safe, happy, and loved while you’re away. 🐾💕 I’m currently home from college for the summer, which gives me a very flexible schedule and plenty of availability throughout the week. I’m available for walks, drop-in visits, pet sitting, and last-minute bookings. Since I have a lot of free time, I’m able to give pets the attention, exercise, and care they need while their owners are away. Your pet’s safety and comfort are my top priorities. I’ll follow all care instructions, keep their routine consistent, and make sure they get plenty of attention and love. I’m happy to send updates and photos so you know your pet is in good hands.

About: Hey! My name is Stefanie and I have been taking care of animals for almost my entire life. I have experience with both cats and dogs and would love to watch your pets for you. I hold myself to the same standards that I would expect from my own pet sitters. I can handle animals of all shapes and sizes, even your giant breeds! I have experience in the veterinary field and have cared for pets with all types of dietary restrictions, medical needs, and temperaments - so if your pet needs some special attention, I'm your gal! I have had dogs for almost my entire life. As a child my family had a Lhasa Apso, and he lived a long and happy life with us. I have had pets of my own since 2014, and all my pups are seniors now - they have a special place in my heart! I also have two sweet young cats and would love to check on your feline kiddos. I am a full time mother so I am readily available for drop in visits, overnights, and walks. Please note that my infant son will be with me during all visits. I will of course assume responsibility for my kiddo being safe around your pets, but please be mindful of your pets' temperament with children when booking! My ideal scenario when caring for your pets is to adopt their current routine - I find that keeps them the happiest while their people are away. I'm happy to visit on whatever schedule is best for you, and I'm happy to do overnights as needed.
“My fur babies are happy and healthy, and Marti was in constant communication with me regarding their care during my week away. Everything went smoothly and I would definitely recommend her to care for any and all fur babies!”

“Shanice was excellent taking care of Kori while we were away for the weekend. She even went above and beyond to make time in her schedule to come early one of the evenings to make sure Kori got her walk to avoid a huge rainstorm that came! Thanks Shanice!”

About: I enjoy walks along with training them new tricks. I like giving them lots of love and attention as you can see in my profile picture with Nala. I grew up with a lot of animals when I was younger and it’s just always been a passion to be around animals and enjoy there presence. My mother would always be upset when I brought every stray home and nurtured it till it got adopted. Feeding them and giving them shelter always made my heart smile. Making sure they enjoyed human contact was a big thing for me especially when they were separated from there parents or if they were just strays. If I could I would have every stray stay with me to care for them.
About: Having my own dog and being raised in a family who always had two dogs has given me expertise in caring for dogs, I will treat all dogs as if they are my own I’m currently not working while I wait to start residency in July, I am open and available to care for your dog anytime of day! My house has a fenced in yard and no cats. I’m willing to come to your house, if that is preferred, just let me know and I can work with you
“Bailey was great with my cat who is very shy. Bailey took very good care of her and was even able to get Poppy to come out and greet her and she sent pictures to me. Very pleased, will hire her again!♥️♥️♥️”
About: My experience may not be as much as some but I’ve worked with my own dog (standard golden doodle) enough to know what kind of care and fun they need! I work the early shift so I’m able to provide afternoon care. Walks, potty breaks and doggy parks provide just the relief your babies want! After a long day cooped up while your at work, your pet will be sure to be happy for a little friendly visit and some exercise.
About: I have taken care of dogs and cats ever since I was young. Family, friends, and others have trusted me to take care of their babies while they were away. I will walk, feed, bathe, and play with your pets while you’re away so that they are safe and comfortable until you come home. I currently am just going to school. I am available anytime! I have my own transportation and can come check in on your pets anytime you need. I have a cat of my own and I frequently take care of my neighbors 5 dogs, (2 little, 3 big) and my sisters 5 cats. I have had my own smaller dogs. I promise that you can trust in me to make sure your pets are okay and taken care of at all times.
About: I have had pets my entire life. I’ve always wanted to be a veterinarian and live on a huge farm with as many animals as I can imagine. While this is not my overall goal job, it would be a dream to be able to care and spend my days with dogs and/or cats of any & every kind! When I was about 15 I volunteered at the SPCA for about a year and a half, along with caring & sitting my own animals that have included cats, dogs, rabbits, chickens, and even reptiles! Just about anything you can name to be a house pet, I’ve had and/or cared for/sitted! What you’re looking for in a sitter is what I can provide! I’m open to just about any and every animal, any time of the day, whenever you need it, I’ll be there! I am in school part time but still have plenty of time to play with your fur babies! I have two dogs of my own and care for them on an hourly basis so a couple extra pups is no big deal! I am only in school two days a week and am available full time other than that! I have a large fenced yard and two sweet girl dogs that can keep your pup company! I can also crate your dog if needed! If we are in your home, I will do every part of your normal routine & more to ensure your pup feels safe & comfortable!
About: I have a passion for animals since as long as I remember and believe they should be loved and cared for and they will show you more love than ever. I am a animal lover and can be there to care for them like they were my own fur babies. I have a large fenced in yard for them to play and jump about in and I can provide baths for long stays. I live in a safe neighborhood and can provide walks often for great exercise. I have a wonderful husband and son that can help me with extra care to your pet. Please let me know if you have any questions and I look forward to meeting you and your fur babies soon. I'm avalible for full time care on the weekends and can do drop in visits anytime durning the week. I have dogs and cats of my own and now how to make sure they are taken care of. I have a large fenced in yard with lots of space to run and play. I also have 3 pups to keep your fur babies company.
The median cost per visit for dog sitting in Winona is $20
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.
Meet local sitters who will treat your dogs like family

1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests near you
Select a filter and find qualifying Winona sitters!Sitters in Winona average 5 repeat dog sitting clients
FAQs for Drop-In Visits - Winona
Frequently asked questions about Rover
The average cost for Dog Sitting in Winona on Rover is $19.26 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 319 sitters on Rover offering Dog Sitting across Winona. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winona stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winona choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winona with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Winona. On Rover:
- 96% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 100% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.




