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.
“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: 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 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: 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!
About: I require any visiting pets to be vaccinated and on flea preventitive! I have trained many kinds of dogs for many different things! I have a service dog that I trained Bella! I also have a cat that is trained to sit, spin, and jump! I have experience with diabetic animals and with most animals in general! I am educated on animal CPR and heimlich. 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: ✅ Personalized, Attentive Care We provide attentive, structured, and individualized care for pets of all breeds, sizes, ages, temperaments, and energy levels, always tailored to each pal’s routine, personality, and comfort. Our personalized approach is highly requested by pet parents who value dependable, attentive, and individualized care. Every pal receives thoughtful care—never a one-size-fits-all approach. Our goal is to provide a safe, comfortable, and nurturing home away from home where every pal feels seen, respected, and well cared for. 🩺 Experience With Special Needs & All Species Our experience includes caring for: * Deaf and blind/visually impaired pals * Seniors * Pets with medical or specialized needs We approach every situation with patience, consistency, and calm reassurance. 🔍 Additional Knowledge We care for small pets, birds, and reptiles with proper handling, habitat awareness, and species-appropriate care. We also provide on-site farm animal care, but do not offer boarding for farm animals. 🧠 Professional Experience & Reliability One of us has professional animal-care experience, and we offer reliable, year-round availability, including: * Weekends * Holidays * Last-minute bookings (when availability allows) ✨ 🏡 Supervision & Safety Standards We provide 24/7, full-time supervision during boarding stays, ensuring your pal receives consistent care and attention throughout their time with us. We are highly observant of behavior and body language, allowing us to recognize subtle changes and respond appropriately in real time. ❤️ Socialization & Boundaries Your pal will never be introduced to other pets without prior notice and your permission. We always respect each pet’s: * Temperament * Boundaries * Socialization needs 🤝 Thoughtful Pal Matching When appropriate, we thoughtfully match your pal with other pets in our care based on factors such as gender, age, size, temperament, energy level, experience with other animals, socialization style, and individual needs or conditions. We take the time to consider each pal’s personality and experience level to help create compatible, positive interactions rather than taking a one-size-fits-all approach. Any introductions are handled thoughtfully and with your permission. Our priority is making sure every pal feels safe, comfortable, respected, and appropriately matched throughout their stay. 🏆 Returning Client Priority We value our returning clients and appreciate your continued trust in our services. When scheduling allows, returning clients are given priority consideration and may be offered preference when reviewing new bookings! 📸 Communication & Updates Throughout your pal’s stay, we provide periodic check-ins and updates, giving you peace of mind while they’re in our care. 🕦 We provide reliable, 24/7 care year-round, including weekends and holidays, so your pet can enjoy consistent supervision and attention whenever they stay with us! 🏠 We maintain a structured, comfortable home environment and follow each pet’s individual routine, including feeding schedules, potty breaks, exercise, playtime, rest, medications, and any specialized instructions provided by their family! 🏢 Apartment Home Notice: We live in an apartment complex with shared walls/common areas. If you or your pet have sensitivities, please keep this in mind when booking.
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. 🐾
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
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 $18.87 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 258 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 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 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.
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