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.
“Molly loves when Cory comes over. He takes super great care of her and keeps her in the center of his attention. It means a lot to me to know that she is being looked after by someone who shows her so much love.”
About: I am retired. I will spend quality time with your dog! I have owned dogs all of my life. Our little Maddie went over the rainbow bridge November 2025 (at age 13 1/2). We miss her but have not taken the plunge for our next dog. Waiting on that special one to enter our lives! In the meantime, I am just pet sitting and enjoying other's dogs. When friends and relatives visit, their dogs are welcome too. Our home is totally dog friendly. We have a fenced in yard, as well as 7 acres to roam with a leash. If they enjoy riding in a side by side, we will go for rides. I am retired. I have plenty of time to play with your pup, and I will make sure they are well cared for, never left alone outdoors, and I have experience with giving medication too. Walking, playing and snuggling will be a part of each day. I have a fenced yard. I get up early to let them out to go potty. Potty breaks are as often as needed. I have experience with all size dogs.
About: I have been taking care of cats, dogs, various rodents, and birds since I was old enough to reach the sink to fill their water bowls! My professional dog walking and pet sitting experience began in 2012 when my employer at the time needed someone to watch her three dogs, two birds, and several needy houseplants while her family took a two month long vacation out of the country. I enjoyed the experience so much that I found a pet sitting and dog walking service to work for and was with Mutts of Greenwich for two years before I began to do pet sitting in my hometown of New Canaan, CT. I offered cage and aquarium cleaning services for my clients as well, which they loved! Having moved to Colorado Springs, I look forward to creating a great relationship with new clients (and their owners!) here in town :) As a full-time student with online classes, my schedule is extremely flexible which makes petcare a great fit. I am able to set appointments and do my schoolwork around them. There is nothing like a good walk with a cute doggy to help reset my brain after a hard assignment! My fenced in yard is safe and provides my 3 cats and 1 dog (and multiple squirrel and bird families) with a little piece of heaven. I also love being able to care for my pet friends in their own homes where they are already comfortable and safe! I have cared for ferrets, parrots, guinea pigs, peacocks, rats, hamsters, dogs and cats of all shapes and sizes and even snakes. I am also experienced with giving medications and assisting special needs and elderly dogs and cats.
About: I have so much energy for walks and training puppies I’ve taken care of dogs of every kind since I was 15 Neighbors, friends and family have relied on me to walk, feed, training and bathe their pets I have a mariachi band and we just work on Saturdays, we have a big indoor space and 2 large outdoor spaces for the animals I like to play ball with the dogs in the fenced-in yard at least twice a day to expend their energy. I like to have meal times and also a little training in case it's a puppy, I always have fresh water and toys
“Teja was absolutely wonderful with my dogs. She treated them with love and care as if they were her own. I am so grateful for her help. She is very responsible and reliable. I am so thankful for her. She took care of everything that needed to be taken care of and did extra on top of it. She wasn't late and gave me peace of mind while I was on vacation. I had a lot of anxiety about leaving my dogs but Teja really came through for us. She was super friendly and kind to my dogs. She really took a burden off me and I will always be grateful for her assistance. She has great attention to detail. She gave thorough attention to us through the app and our dogs, making sure everything was safe and secure at home. Teja is a very lovely person who truly has a giant heart for doggies! 10/10 Would recommend”
“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!”
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.
“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 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!
“Harleigh goes above and beyond. We had a family emergency and had to leave town quickly. She helped on me out on such short notice and made a very stressful time so much easier. I know my crazy pups are in safe hands with Harleigh. We are so appreciative of her and will continue to rebook with her!”
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 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.
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
About: I have cared for many dogs in my life. I have cared for friends' and family's dogs, as well as my own, ranging from chihuahuas to great danes. I have yet to meet a pooch who doesn't like me. I will provide individual quality care to each pup and will willingly help with any extra pup related requests (Baths, brushing, and medications). I am also always available by phone if you would like to ask any questions about me or how I will help take care of your precious pup. I know that each pup is an important member of the family, and assure that I will take the best of care of the pup or pups. I'm Alexis and I will be your pup's best friend! I'm a college student so my schedule is pretty open and flexible. Perfect for all your dog's needs! I always open and honest about my schedule and will never cancel last minute. My goal is to keep your pet happy and maintain their routine. I'll always have my eyes on your dog whether it's at home, on a walk, or at a dog park. I also strive to keep your home how you left it though if you need a few chores done I don't mind helping out.
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.
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
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 June 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 June 2026, there are 321 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.
Connect anywhere with the Rover app
