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 82 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: My family has owned dogs and cats my entire life. I don’t think there has been a single day in my life where I didn’t own a pet or have responsibility for one. Including the Marines under my charge. Animals. Seriously, though… Pets love me. I am also a firm believer in following instructions to a T. People are often surprised when I ask to meet their dog, they tell me that the dog is skittish or afraid, and then the dog walks slowly up to me like they’ve known me forever and then we’re best friends. I feed my two cats, Chief and Cosmos, daily at 8am and 8pm. Cosmos requires special dietary food, so my wife and I bought chip-specific feeders for each cat. I also make sure they stay physical with my fishing rod toys, as well as ensure clean facilities for the… you know. It all comes down to showing them love, providing for them, and protecting them. I treat my two cats like they were my own kids. We don’t deserve their love if we can’t give it to them. It’s inhumane.
About: I have about 7 years of pet handling experience from my own animals to volunteering at animal shelters in LA. I have worked with dogs and cats of all ages, from puppies to seniors. I have gained experience from my own dogs, one of which was blind and deaf. With over 250 hours volunteering at my local city animal shelter, I gained additional experience caring for cats, dogs, rabbits, hamsters, and guinea pigs. I cannot wait to meet your furry friend! I currently have a very flexible schedule. I am usually busy on the weekends, but I could make myself free if I am given enough notice. When caring for a client’s pet, safety is very important to me. Following the owner’s rules and ensuring your pet is cared for and loved while you are away is my number one priority :)
“Molly was great! She took amazing care of my cat she even bought her toys, I’ll definitely be in touch with her again if I need anyone to look after my cat! Couldn’t be happier!”
“We have *never* come home from a trip with our cats so happy and unstressed as they were with Kimberly taking care of them. Even our older, anxious cat who usually hides from all pet sitters was happy to come out and see Kimberly during her visits. I also really appreciated how proactive she was with communications, and how understanding she was about the state of chaos our house was in since we are still moving in.”
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.
“I’ve had Sanaz as Argos’ regular dog walker now and she is so great with him! I appreciate her flexibility and optimism when I have last minute changes. Highly recommend!”
“Geena is amazing with both our small and big dog. They’re both a little bit rumbustious and she definitely handles them with grace and love. You can really tell she loves dogs and takes her job watching over them very seriously. She’s also trustworthy and i felt very comfortable and safe having her come inside my home and watching our dogs. Im very grateful to have found a dog sitter who my dogs look forward to having come over.”
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 🫶🏻
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: I have owned pets most of my life. I understand that every animal is different, so I’d love to take the time to get to know your pet. I have no doubt we will bond! I’m currently in-between jobs. I typically work remotely, so I’m pretty flexible. I’d love to have regulars when I can bond with your animals. ❤️ In my own home, my dogs are a bit spoiled. They’re older, so I want them to be as comfortable as possible. They never worry about food, water, walks, play time, and love! I’d be the same with your animals!
About: What sets me apart is the love and patience I have for animals. I personally raised my sweet dog since she was just one month old, so I understand how to care for young puppies with tenderness and responsibility. I may not have formal experience, but I treat every pet as if they were my own — with love, respect, and attention. I truly feel a connection with animals and enjoy making them feel safe and happy. I’ve also helped care for pets of family and friends, and I always do my best to make them feel loved while their owners are away. I have a flexible schedule that allows me to dedicate time to pet care during the mornings and some afternoons or evenings. I enjoy being active, so going on walks or playing with dogs fits perfectly into my daily routine. I’m very responsible with time, and I love spending quiet moments giving attention, cuddles, or just making pets feel safe and loved. When caring for pets in a client’s home, I make sure to follow all instructions closely to keep their routine as normal and comforting as possible. I give them fresh water, food, walks, and lots of attention — always with love and patience. I respect the client’s home as if it were my own, and I keep everything clean and organized. I also take time to connect with the pet, understand their behavior, and make them feel safe while their owner is away. I truly believe animals feel our energy, so I always bring calm, kindness, and warmth to their space. I care for them like I would want someone to care for my own dog.
About: My girlfriend and I work from home and are able to provide full time care for your pup! We have a large fenced in area that is great for play dates! Both my girlfriend and I work from home on an alternating schedule so one of us will always be home to care for your pup! Our dog is an inside/outside dog that is free to go in and out as he pleases. We keep our doors open all day so they never have issues trying to get out into the yard.
“Almira did a great job sitting my cat while I was on a long vacation. She is reliable, accommadating, and communicates very well. I was able to be away without having to worry about my cat. I would definitely use her service again!”
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.
About: Lived with and taken care of dogs my entire life, both medium and small sizes. I love all animals and my priority is keeping everyone’s furry loved ones happy, healthy, and safe during their time in my care. ❤️🐾 I am currently working part-time so I am home the majority of the day, which means plenty of time to play with and care for your pups. I make time for 1-2 solid walks a day, and am able to provide plenty of affection and care. There are two other adults living in my home who also love dogs and caring for them, so chances are someone will always be home to let your puppy out to do their business or to entertain them, even when I am at work. I have a private backyard where pups can sunbathe or do their business. Dogs are welcome on the furniture in my home, and are always treated with love. We have a lovely neighborhood where we will take our daily walks, and plenty of comfy spaces and beds for your pups to sit back and relax.
“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.”
The median cost per visit for pet sitting in Winnetka is $25
Pet parents share their Rover experiences - Winnetka
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!
Adriana is a natural with cats. We have two cats, one is outgoing and friendly, the other is shy and friendly. I didn't think she'd see the shy one for a few days, but during our meet Adriana sat down and the shy cat came running to her. Adriana visited the cats daily while we were away, took care of everything on our checklist and provided great photos along with a summary of each visit. 10/10 would recommend!
Halle provided 3x a day drop in visits over four days. She was always on time and stayed with Luka for at least the the amount of time requested. Halle did everything asked of her and bonded nicely with Luka. So much so, that I'm sure Luka was hoping that it was Halle at the door instead of us. I would gladly have Halle watch Luka again.
Athena was fantastic, not at all fazed by having three dogs at once, one of which can be a little hard to handle. A true professional who has experience. Athena is friendly with a calm manner that helps the dogs feel more at ease. I have already rebooked, highly recommended.
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet & Greet
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 near you
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 $27.75 per visit (as of June 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 June 2026, there are 16,034 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
- 93% 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.
Connect anywhere with the Rover app
