Pet Sitting Winnetka
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 169 pet parents in Winnetka have booked pet sitting
Winnetka, Find top rated pet sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
About: I’ve been around dogs since I could walk, and I know that every pup has their own unique personality and pace. I’ve had my own dog, Paloma, for five years now, so I’m well-versed in the routine and the responsibility. Whether your dog wants a high-energy trek or just a slow sniff around the block, I’m happy to follow their lead. I’ve got a flexible schedule and a very relaxed approach—I’m just here to make sure your dog has a great, stress-free time while you’re busy. I’m currently in a bit of a transitional period with my schedule, which means I have a lot of flexibility to prioritize your dog's needs. Whether it’s mid-day check-ins, afternoon walks, or weekend sitting, I can easily work around your timing. I'm usually around and available to provide consistent care and plenty of attention throughout the week. I live in a quiet, gated community that provides a secure, low-stress environment for your pup. My home features a private yard and court for safe playtime away from traffic. Beyond that, I live in a very walkable neighborhood and love taking dogs on more scenic adventures. Whether it’s a trip to a local dog park for some socialization or a nature walk to explore local trails, I’m happy to tailor the outing to your dog’s energy level. Having had dogs my whole life and caring for Paloma for five years, I’m always focused on keeping them safe, hydrated, and happy while we explore.
About: I’ve always had dogs growing up so i grew up a dog lover! I recently got a kitten and i’m in love with her. I’ve always been around animals and taking care of them. I work part time and have time to give other pets care when needed. I start school in August so my time will be less but for the summer i am free. I have two dogs in the back and a cat in the house. I’ve always grown up tasking care of the dogs my family have. Currently I take care of my cat for the most part bathe her when needed, feed her 3 times a day, and provide enrichment.
About: What sets me apart is the level of care and attention I bring to everything I do. I'm an active person who genuinely loves spending time outdoors, so taking dogs on fun, engaging walks is something I truly enjoy, not just a job. I'm dependable, detail-oriented, and believe every dog deserves individualized care. Whether that means sticking to their usual walking routine, making sure they get plenty of exercise, or giving them extra patience and affection, I'll treat your dog as if they were my own. While I don't have professional dog training experience, I have cared for and trained my own puppy, which taught me the importance of consistency, positive reinforcement, and paying attention to a dog's unique personality and needs. I'm committed to providing a safe, reliable, and enjoyable experience so you can have peace of mind while your pup is in my care. Pet care fits seamlessly into my current routine. I have a flexible schedule and full availability throughout the week, which allows me to dedicate my time and attention to each dog I care for. I genuinely enjoy being active and spending time outdoors, so dog walking is something I look forward to every day. As I'm exploring my next career opportunity, I have the flexibility to provide dependable care, accommodate different schedules, and give each pet the attention they deserve. Whether it's a daily walk or a last-minute booking, I'm committed to being reliable, responsive, and making sure every dog has a safe, fun experience. When caring for pets in a client's home, my priority is making them feel safe, comfortable, and well cared for while respecting the routine they're used to. I know how important communication is, so I'll provide updates and photos after each visit so you can have peace of mind knowing your pup is happy and in good hands. I'll also treat your home with the same respect and care I would my own.
“Quick and easy communication and was on time for every visit! Our dogs loved her and we are so thankful Molly was able to help. Cleaned up a few accidents, and made great notes so we always knew what was going on. Would recommend to everyone”
About: Neighbors, family and friends can always count on me for dog sitting with a simple food or water, attention, play time and lastly walks around the neighborhood I currently work part time and my job gives me a flexible schedule, so i have plenty of time! i’m available for walks around your neighborhood and even some play time at home My services includes me going to the clients house feeding, taking out to use the restroom, and engaging with the pet. Depending on the service I can check in multiple times a day and update the clients by sending pictures or videos. I also offer walking services for pets.
“Ariana is absolutely wonderful! She took such amazing care of my cat, Juju. I could tell from her updates that she wasn't just checking off a list, she truly bonded with her. She even stayed longer than planned because Juju fell asleep on her lap and she didn't want to wake her! She also sent several photos and notes, and communication with her was easy, so truly it was relief knowing my pet is with someone so patient and caring. Highly recommend! :)”
About: I have always enjoyed being around animals ever since I was a little kid. I have owned and cared for rabbits, dogs, fish, turtles and parakeets. I work full time as an educator so most of the year I am only available weekends. However I am currently available during weekdays due to spring break. I would be happy to care for your pet in my home or at your home if that is your preference. I have one dog at home which would be kept in a different area.
“I had a great experience with Anna. I was comfortable leaving my 2 dogs with her while I was traveling. She was taking good care of them, made each visit on time and kept me updated about everything.”
About: I have taken care of cats and dogs since i was a teenager. I have walked all sizes of dogs and taken care of all types of cats. I am a cat owner myself of a senior cat who is 17 that i have had since he was a kitten and a 2 year old tuxedo cat both of who are adorable. I love all animals. I’m currently unemployed so my schedule is very flexible. I am looking to take on pets as i love animals and have time to help care for them right now I will ensure the pets are fully fed and taken care of. I will follow any specific instructions and give updates through the day. Your pets are in good hands.
About: We’re a friendly, reliable married couple with 26 years of combined pet care experience, offering personalized, loving care for your furry family members. Our services include daily walks, playtime, pop-in visits, and doggy playdates or daycare. We share our home with our 5-year-old Brittany Spaniel, who’s well-socialized and gets along with nearly every dog she meets. Whether your pup needs a fun day with friends or just a little extra love while you’re away, we’re here to make sure they feel happy, safe, and right at home. Pet care is a full-time part of our lives right now, which means we have plenty of time to give each client’s pet the attention, care, and love they deserve. Our flexible schedule allows us to be fully present for every visit—whether it’s feeding, playtime, or just keeping your pet company. We treat every animal like family and make their well-being a top priority in our daily routine. In our home, we offer a safe and engaging environment with a fully enclosed front and backyard where dogs can play and explore. We share our space with our 4-year-old Brittany Spaniel, who is well-socialized and loves the company of dogs of all sizes. We don’t crate dogs unless they are already crate trained and their crate is provided by the owner. We spend plenty of time playing, interacting, and attending to each pet’s needs based on their unique personality and comfort level. When caring for pets in our clients’ homes, we provide the same personalized attention—whether it’s playtime, feeding, or quiet companionship. We make it a priority to understand each animal’s temperament and routine so they feel secure and happy while you’re away.
“Kimberly has been very kind and is a great pet care giver. She knows what to do as far making your pet feel very comfortable with love and attention. Thank you Kim for taking care of our 6 year old cat Honey 😊”
About: I have 3 dogs at home, two small and one large. I have had dogs all my life and I am comfortable with dogs of all breeds and sizes! I understand the importance of the first time meeting a dog and will be patient until they feel comfortable around me. I have worked with rescues before saving dogs from the streets which is where I learned a lot of my dog skills as well. I love my walks with my dogs and would love to walk yours! I do currently work full time but I am available after 5:00 PM Monday - Friday and all day on the weekends. I hope to get to meet your dog or dogs soon! I currently work full-time but am available for evening walks after 5 PM on Monday - Friday. On the weekends, I am available all day! I have experience dog sitting and always follow the instructions the owner has left for me. I am a guest in the home and always make sure I am on top of all my duties. I triple check everything is the way it should be prior to heading out the door to ensure the comfort and safety of my clients pet.
“Almira was amazing! Had a family emergency and had to leave town super fast so had coworkers tag team watching my dog. Turned complicated so I looked at rover to see if anybody can help super last minute and Almira absolutely saved the day. Thank you so much for everything! Will definitely be contacting you again.”
About: After working at several high quality pet supply companies, I know a great deal about pet nutrition and pet care. I have owned dogs and cats my entire life. I have experience with large dogs, we always had/have German Shepherds, and small dogs, as well as cats. I can take care of seniors, adults, and puppy’s; I have experiencing administering pills, and putting additives into the pets food. I can bring my lifelong pet ownership experience into caring for your lovely pet. I love learning new things about different breeds and different personalities. No pet, like no person, is the same nor should they be treated the same. I am excited to get to know your pet and their unique way of living life! I’ve just moved back to LA from spending 6 years in the United Kingdom, so your pet will be my full focus as I’m not otherwise employed currently. I take care of your pet(s) as if they are my own. I take any special requests seriously and have clients who have used me for years and trust me in their homes. I understand how serious that is, and take respect to the highest level, paring that with safety.
About: So many friends and neighbors wanted me to take care of their dogs when i was just a kid cause they knew that i can understand their language. I was taking care of dogs and cats just as a hobby only for people i knew, but decided i can help more pet owners and make everyone’s life easier!! I have experiences with puppies and senior care. You will be receiving really nice photos of your pups🐶 I am at home 24/7 if needed no problem with that, home is fun with a furry baby we can watch movies and cuddle!!! I know that all doggies need different care. I am very good at potty training and obedience training. I also have first aid training🤍 Please read the following before booking either of these services: Day Care means: Between 0-10 hours Boarding means: Between 10-24 hours All of the pets i take care, they are my babies too!! They are all welcome for hugs and most importantly LOVE! For summer period i am free every day and i can start working really early if my client needs. I don’t like to go for walks so late for me and my client’s safety. I have a nice fenced backyard; we mostly play there and hangout i don’t let them out unsupervised. I only walk with leash, sometimes dogs see rabbits or squirrels and chase after them. We don’t want anyone to get hurt or scared 🫶🏻
The median cost per visit for pet sitting in Winnetka is $25
Pet parents share their Rover experiences - Winnetka
Andrew was amazing! He helped me out last minute, and I was so thankful he was available. He took great care of my dog, kept me updated, and made everything so easy. It gave me so much peace of mind knowing my dog was in good hands. I’d definitely book with Andrew again. Thanks so much!
Emily is fantastic! She completed her drop ins at the time scheduled and sent lots of pictures. You could tell my cats were super happy with having her there. Even my super scaredy-cat warmed up to her while I was away my schedule is just all over the place and she was so accommodating to last-minute changes as well which I really appreciate.
Caira was wonderful! She was very sweet and I felt comfortable leaving my cat in her care. She even took the time to meet my cat beforehand, which I greatly appreciated. It gave me peace of mind knowing my cat was well looked after. I would happily book with her again.
Sanaz took wonderful care of my two cats while I was away for two weeks. She visited every day to feed and check on them, and she consistently sent photos and videos that gave me peace of mind while traveling. She was reliable, responsible, and a pleasure to work with throughout the entire experience. I came home to two happy, well-cared-for cats. I would definitely book Sanaz again and highly recommend her to anyone looking for a trustworthy pet sitter.
We are so happy we found Cecilia to take care of our two cats. It was a huge relief to be able to relax and enjoy our vacation knowing that they were in good hands. Cecilia was super responsive to messages, very reliable and consistent with time, and she even managed to get our very shy rescue cat come out to say hello! The photos she sent every day made us smile and we knew the cats were happy based on their behavior. We would highly recommend and will absolutely be booking Cecilia again next time we travel!
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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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 pets like family
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Select a filter and find qualifying Winnetka sitters!Sitters in Winnetka average 6 repeat pet sitting clients
FAQs for Drop-In Visits - Winnetka
Frequently asked questions about Rover
The average cost for Pet Sitting in Winnetka on Rover is $21.09 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .
As of July 2026, there are 16,443 sitters on Rover offering Pet Sitting across Winnetka. 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 Winnetka 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.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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.
Yes, you can find sitters who have experience with handling special pet needs in Winnetka. On Rover:
- 89% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 96% 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.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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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