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.
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 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: I have had a dog or cat in my life for over 5 decades. My parents raised dogs and taught me early in life how to care for pets. My heart has always belonged to some sort of pet from rabbits, guinea pigs to dogs and cats. Big dogs, smaller dogs and everything in between. I have loved them all. I am confident in my love and ability to care for all pets and appreciate my time with them. I feel pets are an essential part of my every day life. I am a Doggie Mama to 3 Basset hounds and a Rat Terrier who thinks he is a Basset hound. Our life is really blessed and very good and we wouldn't change a thing.
About: Hello! My names Summer. I am 30 years old and I work full time as an animal hospital employee. I've been trained to properly medicate and can also give shots such as insulin. I do not mind coming to your house or your babies coming to mine. I will work with whatever preferences you have. I have a fenced in backyard and live right down the road from a park/lake. I also do not mind any house keeping you may need while I'm there such as watering your plants, laundry, or anything similar. I have five years of experience with all types of animals and do not discriminate on any kind. 🐶🐱🐭🐹🐰🦔🐸🐢🦎🐍🐟🐠 Message me today and see for yourself if I'm a good fit for you and your pets. I work Monday-Friday 7:30 AM to around 3 PM. I have an hour lunch at 12 and can make brief stops if you’re located close enough. Otherwise I don’t mind making stops before and after. Unless I’m staying at your residence and then that will be handled as discussed. I will follow any discussed routine. I am capable of providing medical care such as medication and handling any handicaps they may have with the utmost care.

About: I have experience dog sitting small and big dogs, and pet sitting for families I know, including caring for my bosses’ dogs and cat when they were away. I also grew up with a dog, so I understand how important it is to give pets love, attention, and a safe routine. I’m comfortable helping with feeding, walks, basic care and keeping owners updated while they’re away. I always make sure to follow each pet’s normal routine and any specific instructions from the owner, because every dog has their own personality and needs. I currently work part time and remote, so my schedule is very flexible. I can help during the day and/or over night as needed I cannot bring pets home as I live in an apartment where no pets are allowed, but I can definitely go and stay at clients house as needed
“She worked with me with my 3 puppers, and was able to drop in without meeting them ahead and made them feel so safe and happy. One of my little ones has bad anxiety and I’m so grateful to her that she came and saw them in the middle of my long shift and gave them an outside break to play!”

About: I have a significant amount of experience caring for my own little spaniel of 15 years, who thrived and loved life before passing. I have pet sit for a handful of family friends on several occasions and fall in love with every dog I meet. In the past I have worked with my grandmother, who used to be a local breeder in her town. I learned a lot about caring and nurturing newborn puppies, especially as they grew older. I’ve also obtained experience working at a Petsmart grooming salon, where I gained valuable insight into the process of bathing and grooming various breeds! Although I do currently go to school full time and work a part-time job on the weekends, I am looking for opportunities to do drop-ins and dog walking. I love to be outdoors, so if you have a dog that loves a good hike and long trail, I’m on board! I also love to stay in if you are just needing someone to check in on your friend and care for them in your absence. I do over night stays if needed as long as it works around my current schedule, I am more than open to discussing details if necessary. Anyone’s pup would be safe in my care, I love to treat any animal I interact with as if they were my own. It’s always my first priority to ensure that the animals I care for do not go hungry, get bored, or feel lonely. Know that your bestfriend would be well watched after and receive lots of love by me. I am a dog person through and through.
About: I have been so fortunate to care for and love on many dogs from puppy age to senior, both big and small! My soul dog of 16 years dealt with heart issues the last few years of his life which gave me the skills to track, administer, and monitor his schedule as needed. I have also had pups who've dealt with stomach and skin issues, so i am experienced in that aspect as well. I have a very flexible daily schedule as I work from home and spend the day taking care of furry friends. This gives me ample opportunity to give your pets all of the love and care that they need while you are away! When caring for pets in your home, I always ensure that they stick as close to their normal routine as possible to ease their stress. It is important to create a stress-free environment and a calm relationship between myself and your furry fam!
“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”

About: I’ve taken care of dogs since I was young. Also I’be work at different vet clinics through my life.so I have the experience to take care of your animals in best way possible. I’m currently a bather at my clinic so if baths and nail trims is something you want added on that is something I can do for you as well. I do work during the week but have weekends off and if it close to work during the week I can stop by during my breaks to play and let them out to potty. I have my own furry babies that are super friendly to play with if you want that environment or they can have my divided attention.

About: Animals have always been a big part of my life, both professionally and personally. I worked at Shelley Drive Animal Clinic for four years, where I cared for dogs and cats by administering medications, feeding, cleaning kennels and litter boxes, monitoring their health, and ensuring they were comfortable and well cared for. Outside of work, I have a farm where I care for my horse and two dogs, giving me hands-on experience with animals of different sizes and personalities. I earned a bachelor’s degree in Animal Science and am currently pursuing my master’s degree in Animal Science. Whether your pet needs playtime, medication, or extra patience and attention, you can trust that they will receive compassionate, reliable, and knowledgeable care with me. Pet care is woven into my life through work, farm responsibilities, and animal science studies, giving me hands-on experience and compassion for animals each day. Your pet’s safety, happiness, and comfort are my top priorities. I will provide a loving, safe, and stress-free environment where your pet feels secure while you’re away. Every pet will receive plenty of attention, affection, playtime, and personalized care based on their individual needs and routine. Whether it’s feeding, administering medication, going for walks, or simply providing companionship, I’ll care for your pet as if they were my own. My goal is to give you peace of mind, knowing your furry family member is in compassionate, trustworthy, and capable hands.
About: Veterinary-experienced pet sitter specializing in cats, senior pets, medications, and pets needing extra care. Injections, medications, and a little more love go a long way! I work full-time, but I have 2 cats as well, that would love to meet your pets! I would love spending my off days watching or keeping your pets too! I am well trained on medicines and foods. I’m good with crate training or anything else known before hand. My pets will be at my house, but they are very excited to see other animals. I can feed your food at request or what I have on hand!
“Ebony is great! She communicates very well so she knows exactly what is expected from her. She even check on a non-pet related item for me when I asked. I came hope to happy and healthy pets. I will definitely hire her again!”

About: Experienced animal lover and caregiver 💕 I have three cats of my own and a chameleon. Currently I am a Primate Zookeeper at the Houston Zoo and have my Master’s degree in zoo management. I have experience with cats and dogs of all breeds. Dog Training and Postive Reinforcement Training certified. All pets welcome! 🦜🦎🐈🐾🐹💕 As a zookeeper I get home early in the day and would love to help others feel that there animals are receiving top notch attention and care. I am off on Mondays and Tuesdays and am flexible. I feel that play is a huge part of every animals life. Making sure that they stay safe is a given while providing there essential needs is crucial and any concerns I have will always be addressed with owners as open communication to me is so important. Pets are family ❤️
About: I was a volunteer at a pet shelter, and got "dog walker certified" and also bathed multiple dogs, I can also give them their meds!! My college classes will start in October , and I am not currently working as of right now but in the process of getting a job that is pretty flexible, so whenever you and your pet needs me, I will be there!! I will make sure they have clean bowls and water, clean up after the messes they make no matter what kind that may be and will give them extra EXTRA love and make sure they are all played out, because no one wants to be sitting at home all day doing nothing!!
About: Experienced and devoted pet sitter with a heart for all creatures. Proud parent to three cats and a dog, providing exceptional care for every furry friend. I’m a full time student at TJC and I’d love the opportunity to assist pet parents, offering a helping hand and genuine love for animals to ensure their furry companions receive the best care possible. I would love the opportunity to be a trustworthy and reliable pet sitter as a fellow pet parent, providing the same love and care to others' beloved pets as I do to my own, ensuring their well-being and happiness.
About: I have been taking care of all sorts of animals since I was a little kid! Whether that be farm animals such as horses, cows and goats to household pets like dogs, cats, and birds. I have volunteered at multiple rescues, have my animal science degree, and a currently work in Veterinary sales. I currently have a full time job, however I am always looking for ways to make extra money and get to meet new fur babies on the weekends or evenings! I care for your pets as if they are my own, as I know how important they are to you. I will be able to do whatever is needed to make sure they feel comfortable!
About: I have been a dog lover since my first dog followed me home at the age of 6 (and he was a full size Doberman of all things). I currently have a German Shepherd, Pit bull Mix, Husky Mix, Chihuahua Mix and an Orange Tabby so I'm used to animals of all sizes and temperaments. My poor Pit Mix has allergies, my GSD has hip dysplasia and my Chihuahua has a heart condition, so I'm well versed in special needs! I do research constantly and spend lots of time talking to our vet about how I can make their lives, and mine, easier. I'd love to put all that knowledge to work for your fur babies! I know CPR for dogs and even keep a doggie first aid kit in my car! Just in case. I do my best to make sure my presence is felt as little as possible in your home but that your baby gets all the attention they need and deserve! I'm currently dog and cat grooming only on Fridays and Saturdays. So usually Sun-Thurs its just me and my pets living our best lives. I have a two acre property that we constantly explore and we love to go swimming at the nearby lake! I do my best to be as unintrusive as possible when in you're home! Letting me know their favorite toys and activities do make things easier for us to bond! I have a fully fenced in half acre with another acre and a half we can explore while leashed! There are cows, chickens and other animals on the farm next door so there's plenty of sights (and smells)!
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?
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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
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Popular requests for dog sitting - Winona
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winona average 5 repeat dog sitting clients
FAQs for Dog Sitting - Winona
Frequently asked questions about Rover
The average cost of Dog Sitting in Winona on Rover is $19 per visit as of October 2026. Most bookings cost between $19 and $19 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 309 sitters on Rover offering Dog Sitting across Winona. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

