Dog Sitting Winona
Book a Winona dog sitter to watch your dog in your sitter’s home or yours.
Over 48 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 joined Rover to help feed my love of multiple pets! Since I travel occasionally, managing one dog & cat full-time is enough for me. However, I grew up with 3 to 4 dogs on average. Choose me and your pet will have all the love and attention! I’m in my 30’s and work from home remotely M-F. I volunteer at multiple rescues, so have recent experience with different dog sizes and breeds. When I was younger, I use to be an AKC Junior Handler in dog shows. My personal dog experience ranges from Papillons, Lab/Golden Retriever mixes, Goldendoodles, and a Doberman. I’ve also owned multiple cats growing up, so are also available for feline drop-ins. I even have experience with tiger cubs! I spend a lot of time with my animals and will give yours the same attention. I am available for walks, drop ins and overnights. If your cat is accustomed to leash walks as well- I can do that too! I currently work remotely from home so have a pretty open schedule to come take care of your pet at your home or housesit during the week. I take care of your pets at your home so safety is not an issue. This gives my customers an ease of mind that their animal is in it’s normal environment.
“Lauren was very helpful, caring, punctual and was a great communicator for her drop in visits for my cat! She literally went the extra mile and walked up my snowy icy driveway when her car couldn’t make it up! My cat is a bit standoffish with new people, but he warmed up to her after just one visit! I will definitely be requesting Lauren to help out with my cat in the future!”
“Linsie is great! On time, and communicates! Even took my pup to the dog park (she checked first) and was aware of the environment to keep Dewy safe. Appreciate her communication! Highly recommend.”
About: I have worked with animals off and on my whole life. I’ve had four dogs growing up including my current dog. I do have experience with epilepsy since my current dog does have it. I can also help with basic training such as walking nicely on a leash. I am currently trying to find a new career so working with doggos in the meantime will help me in that journey. I am open for walks or checks in during the week, but can only do stayovers on the weekends. I unfortunately can not have pets at my current residence as it is my parents, but I am more than willing to multiple stops or even overnights for your pets. I will love and care for them as if they’re my own.
About: I have taken care of my two pit bulls since the start of high school. I love giving affection to them, including others I have met in person. I used to have a senior dog who had joint problems and needed help on the stairs, bed, and sofa. I also love meeting my friends’ pets and giving them the same affection as I do with my own pets. I do drop in visits, house sitting, and dog walking. I would love to give your fur babies a bunch of affection and care. I’ll make sure to update you regularly with pictures so you know that your pets are in safe hands. Your pets safety is my top priority. For dog walking, I’ll make sure they stay off the road when the pavement is too hot and/or a car is coming. I will also stay alert to my surroundings. I am unemployed, so I have plenty of time to take care of your dogs and/or cats! I will be available Sunday through Thursday. I'll do my best in following your schedule so your pets won't get stressed by any sudden changes. I'll make sure to ask any questions on how to take care of your dogs and cats so I won't make any needless mistakes. I will also send you updates of your pets by sending you photos and texts.
About: I have over 13 years of hands on experience caring for dogs, from raising puppies into adulthood to understanding how their needs change throughout different stages of life. I’ve learned how important it is for dogs to have healthy outlets for their energy, plenty of attention, patience, exercise, and a routine that helps them feel happy and cared for. I currently have a dog of my own, Reese, who I love taking on walks and runs, as well as three cats with their own unique personalities. Having both dogs and cats has given me experience understanding the very different ways animals communicate, build trust, and show what they need. I’m comfortable caring for puppies, adult dogs, high-energy dogs, and pets who may still be learning their manners or training. I believe every animal deserves patience and the opportunity to feel safe, appreciated, and understood. Whether your pet needs an energetic walk, playtime, companionship, or simply some extra love and attention while you’re away, I want to provide the same level of care I would want for my own animals. 🐾 With a flexible part-time schedule and a love for walking my own dog on the daily, I enjoy sharing fun, fulfilling walks with other dogs too. I’ve always been an animal lover and happiest when I’m spending time outside! I have a dog of my own, Reese, who I love taking on walks, runs, and little adventures, along with three cats who each have completely different personalities. Growing up around animals has taught me that every pet is different and deserves patience, attention, affection, and plenty of time to just be themselves. I love getting to know each animal’s personality and finding what makes them happiest—whether that’s an energetic walk, some playtime, exploring outside, or simply having someone there to give them attention. I’m also completely comfortable with puppies, high-energy dogs, and dogs who may still be working on their training or manners. I believe they deserve just as much patience and care while they’re learning! My goal is to give your pet a fun, positive experience while making sure they’re safe, cared for, and getting the attention they deserve. 🐾
About: HELLO! I have been taking care of all kinds of dogs from pups to senior pets who have special needs. I have done stuff like this ever since I was in middle school. I am very flexible with my time. I do have a cat allergy but that won’t stop me from that either! I’m always here to help you’re best friend 😊 Im very flexible with my schedule for a couple months! I can do early mornings to late nights. I’m always able to help with anything! I’m very detail oriented and need straightforward instructions in order to properly care for a pet. The more straightforward the instructions the better! I treat any pet as if they were my own. Maybe a chance to spoil with my special frozen pet friendly watermelon slush for the hot summer days? Or a little trip to get a pup cup? My dogs are spoiled and I miss them so much so this would be a win-win for the both of us 🤣
About: I have owned dogs for over 50 yrs and love working w them and creating a safe space for them to explore. Welcome to my home! I currently work part time as a nurse and will have lots of time to spend supervising your furbabies in my yard. I will treat them as if they are my own and keep them safe. I have a large fenced in yard and doggy door to lead into it. I have a little friendly dog that loves other dogs and be happy to play. I have plenty of time to supervise your pups and exercise them in a fenced in space.
About: I have taken care of my own dog as well as taken family friends dogs on walks and runs. I am currently training for a half marathon, so if your dogs loves long runs or long walks I would love to help them get outside and exercise. I currently am working part time on top of school. Most days I can take dogs on a walk or run in the morning to later afternoon! I currently live in an apartment where pets are not allowed, so for now I will stick to taking dogs on walks and runs whether that’s around a safe neighborhood or at a park.
About: Hi! I'm Jade, an experienced animal caregiver who believes every pet deserves individual attention, patience, and care. 🐾 I don't believe pet care should be one-size-fits-all. Every animal has its own personality, routine, comfort level, and needs, and I take the time to learn what makes each pet feel safe and comfortable. I'm comfortable caring for dogs and a variety of small animals, including rats, mice, hamsters, guinea pigs, rabbits, birds, fish, reptiles, and other companion animals. Please note: I do not offer in-home cat sitting in my own home. I do offer drop-in visits and house-sitting visits at your home, where I am happy to care for your cats and other pets while you're away. Whether your pet needs a walk, a drop-in visit, feeding, playtime, companionship, or someone to stay with them while you're away, I'll treat them with the same patience and care I would want for my own animals. I understand that leaving your pets with someone else can be stressful. My goal is to give you peace of mind by following your instructions carefully, maintaining your pets' normal routines as much as possible, and keeping you updated throughout their care. I'm dependable, patient, observant, and attentive to changes in an animal's behavior or routine. Your pets' safety and well-being come first. Have a pet that isn't a dog or cat? Ask me! I especially enjoy helping families who have animals that can be more difficult to find experienced care for. I'd love the opportunity to meet you and your pets and become someone you can trust whenever you need a helping hand! 🐶🐱🐭🐰🐹🦎🐦🐠🐾 cpr and heimlich trained I'm happiest when I'm spending time with 6 dogs at a time lol it's so much fun! I don't have space to take more than one large dog or 2 small dogs at a time but someday I will! I am working on getting fencing for my yard! I only let 1 dog out at a time. I follow owners feeding schedule. I chart every feeding, drink of water that i see, and every potty break. I send updates daily and am well educated on how to calm an anxious dog!
About: Hello! my name is Kayla, and i’m so excited to meet your furry friend! i have been a dog owner since the time I was a child, and have enjoyed caring for friend and family’s pets over the last few years. I am looking to fill my free time with boarding, house sitting and dog walking and can’t wait to hear from you soon! I work Monday-Friday but can let your pets out during my lunch break. I am free on weekends. I am a single mom and am looking to fill my up my schedule on the days I don’t have my kiddos. Your furry friend will be my new best friend. I love cuddles, being active and going on walks, and playing with your pets. Your doggo will be treated like a member of my family!
The median cost per visit for dog sitting in Winona is $17
Dog parents share their Rover experiences - Winona
Erica & Ciara are the best! My pup gets pretty sad when I leave but the extra time and love they give her makes so much difference. These sitters take time to really learn about all the things that make my animals happy. I always return to a house full of content animals I highly recommend Erica and Ciara!
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
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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 September 2026. Most bookings cost between $16 and $28 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 September 2026, there are 255 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a 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.
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