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.
“I've used Amanda twice now to take care of my pets. Amanda has proved trustworthy and reliable on both occasions. She is always at our home at the agreed date and time and communicates well, letting us know what’s going on with our pets and if there are any concerns or questions. I trust Amanda with my house and my pets, and will definitely be using her again.”

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: 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!
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: 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: Growing up I have always been an animal lover. At my house we have always had all types of animals dogs, cats, pigs etc etc. I am very good with all types of animals and I will treat your dog with the same amount of kindness and love you would treat your dog. I know how stressful it can be leaving your pet with a stranger especially in this day and age where people can be really scary and not trusty worthy- which is why if you trust me you won’t be let down! your fur baby will be in good hands :) I don’t think of it as a job it makes my heart happy knowing that i can help you ease your mind and help take one thing off your plate when traveling :) I currently work part time at the olive garden in longview but I pretty much am able to make my own schedules so i can be available whenever I am needed :) I live on property that is gated so your animal will not be able to run out. I have 4 other dogs that are very well behaved and love to meet and play with new animals however if that doesn’t fit for your dog i also do have secluded areas where they can be kept away from other dogs.
About: When I was younger we had 3 dogs, they were my best girls! Over the years we had rescued 8 cats, one of our cats may have some autism but she is so gentle and just needed some love. The trick is to let them come to you so they see you as a safe space! I currently work part-time but I am not working as much this summer, I may have a few softball lessons since I play college softball. My morning and afternoons are mainly free, in the afternoon is when I workout but I am very flexible! We used to have a fenced in area in our backyard for our dogs and a pool deck (no pool) but had to tear down our deck and now we have a beautiful grassy green area with lots of plants! Our home inside is very pet friendly we have cat and dog toys as well as cat and dog food/treats!
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.
“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’ve had dogs my whole life and have cared for my very own as long as family members and friends. My goal is to give you total peace of mind when you’re away and make sure your pup feels loved, safe, and happy. My schedule is flexible. I work part time so I am unavailable Tuesdays , Thursdays, and Fridays 4pm-11pm. I am also unavailable Saturday 11am-5pm Available all other times when needed I have 2 mid-size dogs that are highly energetic and playful. They love attention and affection. I guarantee to treat all dogs the same as my very own <3
About: I’ve had animals all my life, would adopt every animal I could if I had the room! I pay attention to detail, will keep you updated with good communication! I am a stay at home grandmother and can adjust my time and days as needed to accommodate the needs and care of your loved pets! I have a fenced in back yard for your animals and I have 2 younger fur babies of my own for your babies to play with! I have ample room inside my home for your pets, crates, playing areas and toys!

About: I have been in the veterinary field and pet sitting field for over 10 years, I love animals so much! and will care for yours with love and respect, as if they were my own. I am a full time veterinary technician, but make time for part time pet sitting and pet transportation. I will usually do check ins between 7-8am on the weekdays and Night time check ins around 9pm depending on the week. one week I'll work Friday-Sunday and my check in may be later at night, and the next week I have the weekends free and check ins can be anytime of the day. Depending on distance from my work I can do mid day check ins. I also do over night stays, and have a spot open for 1-2 small animals- same family for boarding. I follow every instruction that is left for me, go above and beyond to keep pet happy. I take pictures and send updates always. I make sure my pets are always left comfortable and safe, well fed and happy. I have a separate, very spacious room where i can safely board 1-2 cats of the same family, or one cat and one small dog, same family. I do have cats of my own but they do not have access to that area. I also accept small critters- reptiles as well. Cage and supplies will need to be provided.
About: Training and playing and teach them from my sign language and give them my love and cuddle and ride in car and treat them good Anytime and any day as needed holiday as needed I will be available mostly if need watch dogs I will love take care as needed Will be there for them and take care of them and play with our dogs friendly, as needed watch them I glad get petting sitting
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: 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: I have had animals and have pet sat my whole life ! I am committed to ensuring your babies are taken care / loved for during any occasion ! 💙 I currently work at Walmart part time, but am always open to caring for your babies without any hesitation. 🥰My schedule comes out a month in advance so lmk & we’ll get them taken care of ! I have a very big fenced in yard along with four dogs of my own (which are all females ages 1 and a half - almost 3 yrs old.) I would love to make your pet feel at home & comfortable whether that be here or there ! 😊I can uphold many commitments of : feeding, walking, potty breaks, play time, baths, & so much more ! Your pet will feel as if you’ve never left!
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?
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
It's that easy! All payments are processed through Rover's secured platform
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 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 August 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 August 2026, there are 310 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.



