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 54 pet parents in Winnetka have booked pet sitting
Winnetka, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I’ve been around dogs my entire life, mostly chihuahuas and rescues, so I’m very comfortable with pups who need a little extra patience, reassurance, or understanding. My hands-on experience goes far beyond casual pet care. At Miami University, I was part of Paws for a Cause, where we helped train dogs to prepare them for working with children or future companion roles. This gave me a strong foundation in obedience training, reading body language, and supporting dogs with different temperaments. More recently, I’ve been volunteering with the Evanston Animal Shelter, working with dogs who have a wide range of behaviors and needs. There, I’ve assisted with medication administration, training sessions, enrichment, and helping nervous or high-energy dogs feel more comfortable and confident. I’m also on a path toward becoming a Physician Assistant, which adds to my calm, attentive, and health-focused approach. I’m comfortable managing routines, monitoring for changes, and making sure each dog feels safe and cared for. Overall, I bring a mix of lifelong experience, formal training exposure, shelter work, and genuine love for dogs of all personalities. Your pet will be treated with patience, structure, and plenty of affection. I work full-time as a medical scribe during the day (9–5), so evenings, weekends, and holidays are when I’m most available for pet care. During those times, I’m fully focused on your pet’s needs—whether that’s walks, playtime, feeding, or just keeping them company. My schedule outside of work is very flexible, so I can reliably fit in consistent visits or longer stays. When I’m caring for pets in a client’s home, I follow their normal routine as closely as possible—feeding schedules, walk times, crate routines, and any training cues you use. I take time to get to know your pet’s personality, comfort level, and boundaries so they feel safe and relaxed. I provide plenty of attention, enrichment, and calm companionship, and I always keep water fresh, watch for behavior changes, and send regular updates so you feel connected. If I’m hosting in my home (or doing extended stays), I make sure pets have a quiet, clean space to settle in, regular potty breaks, structured playtime, and a consistent routine. Safety is a top priority, doors secured, no access to anything unsafe, and lots of supervised time. Whether I’m in your home or mine, your pet gets patient, reliable care with the goal of making them feel comfortable, understood, and well-loved.
“Andrew was wonderful. My two standard Poodles liked him right off the bat. He was communicative, punctual and always happy with a smile on his face even when it rained.”
About: Hi! I’ve been a lifelong animal lover, and I’ve had pets all my life — so I know how much pets mean to their families. My girlfriend introduced me to Rover, and since then, I’ve been all in. I currently walk up to 10 dogs a day and board around 2 dogs each month, and I truly enjoy every minute of it. Whether it’s a high-energy pup who needs long walks or a shy cat who just wants a quiet companion, I treat every pet like my own. I know how important trust is when it comes to pet care, and I always go the extra mile to make sure your furry friend feels safe, happy, and loved while you're away. I’d love the chance to meet your pet and give them the care and attention they deserve! Pet care is a major part of my daily routine. I work in real estate, which gives me a flexible schedule and plenty of control over my time. This flexibility allows me to dedicate consistent blocks of time each day to walking dogs, doing drop-in visits, and boarding pets comfortably in my home. Whether I’m caring for pets in my home or in a client’s home, safety and trust always come first. In my home, I create a calm, clean, and pet-friendly environment. I make sure there are no hazards within reach, keep any unfamiliar pets separated as needed, and provide plenty of space for relaxation, play, and personal time. I follow any routines or rules you provide so your pet feels comfortable and secure—just like they would at home. When I care for pets in a client’s home, I treat it with the same respect and care I would my own. I follow all instructions closely, keep your pet’s schedule consistent, and provide regular updates so you can feel confident they’re in good hands. I’m always attentive to their behavior, energy levels, and comfort to make sure they’re safe and happy throughout the visit. Whether it’s walks, playtime, meals, or quiet companionship, I’m committed to providing a trustworthy, low-stress experience for both you and your pet.
About: I have many years of experience with dog-sitting from energetic puppies to 60 pound golden doodles. I have experience with walking/ caring for more difficult dogs. I’m comfortable with dogs and cats and I love all animals! I’m home for the Summer from college so I have a lot of flexibility. The only times I’m unavailable are July 11-18 and August 10-14. I will keep your home clean and tidy and respect your space like it’s my own. I’m a small person so I can accommodate any living space.
“Shailyn was amazing! She exceeded expectations in every way. From the get go she made it a priority to get to know me and my cat Pepper, ensuring that I felt safe leaving Pepper in her care. She was very accommodating and understanding. I would definitely recommend her to others.”
“Yimei was GREAT. Highly recommend. She went above and beyond taking care of Lucy, my 15 year old very needy cat! Lucy was very well taken care of. Yimei also communicated promptly after every visit.”
“Isabella has been wonderful and adapted to my flight changes during the government shutdown. She took get care of my fur baby and will definitely be using her in the future!!!”
“Adam was able to fit a last minute booking into his schedule! We are very happy with his responsiveness and his care of Gable! He is fantastic and Gable looks forward to more drop-ins w his new buddy!”
About: I’ve been around cats my entire life, so building trust and connecting with them comes naturally to me. I also gained experience dog sitting for neighbors when I was younger, which helped me develop a strong sense of responsibility and attentiveness when caring for pets. Today, I occasionally volunteer at Tails Together Animal Shelter, where my love for animals continues to grow. Whether it’s playtime, walks, or simply providing companionship, I’m committed to making pets feel safe, comfortable, and cared for while you’re away. My schedule is very flexible. I’m an honors student at Depaul on summer break. I’m available to work as early as 8 AM and as late as 10 PM. I have reliable transportation and have always taken being on time seriously. I’ll come to your home and follow any instructions you have for taking care of your babies! I’m organized and neat and understand that cleaning up after pets is part of the deal.
“They are amazing! This is the first time we’ve ever let anyone outside our family take care of our dogs and they truly put us as ease. The dogs loved them and they truly cared for our dogs. Can’t wait to use them again!”
“Andrew did an amazing time helping drop-in on our dog while he was sick and we were out of town. Early mornings, late night. He did so with an incredibly helpful and reassuring attitude. Our dog was so happy to have Andrew keeping an eye on him. I would recommend Andrew to everyone”
About: Ever since I was a child, I have had a passion for dogs and animals of all sorts. Growing up in the Philippines, my relatives found it strange to have such compassion for animals. I'd always begged my parents for a dog while doing avid research and volunteering at pet-related jobs to prepare myself if my dream was to come true. When I was 17, my parents finally agreed to get a dog-- but not just any dog. I wanted my dream dog: an Alaskan Malamute. Huge, stubborn, and a daily shedder, it was a huge challenge I took on myself. However, this Malamute was well trained, house-broken, and friendly. I believe I can take care of a dog of any size, temperament, or history. I am a graduate from the University of Illinois in Chicago with a Bachelor’s Degree in Biology/Sociology. I volunteered at the Chicago Canine Rescue downtown where we play and walk with shelter dogs. I have copious experience with boarding, walking, and overall loving dogs. As a past dog boarder, I understand the care and attention that must be given to a pup to create a trusting bond with them. For more pictures of our past clients and to get a better idea how I interact with your pup, check out this instagram: powerpuffdogs May have to step out a few times a day, or if I have an outing I would make sure your pup has had plenty of exercise and pets before leaving. I adhere as closely as possible to the pet’s existing schedule— routine is key! Other than that, if you are comfortable with it, I can take your dog on forest walks, dog parks (only if you’d like, and with ample supervision), or on play dates with my own well-socialized dogs!
About: I have taken care of two dogs for the past 14 years. Unfortunately, our oldest passed away in October. Both dogs were inseparable since puppies when we rescued them fron a shelter. I have availability every day but times may vary week to week. I will be able to accomodate requests with a days notice. Availabilty evenings and all weekend is most open as well most weekday mornings. I aleays ensure both a harnesss, collar and tags are used. Also, will always take advantage of secure, fenced yards. When walking with the dog, i am always careful with other dogs.
The median cost per visit for pet sitting in Winnetka is $20
Pet parents share their Rover experiences - Winnetka
Shailyn was amazing! She exceeded expectations in every way. From the get go she made it a priority to get to know me and my cat Pepper, ensuring that I felt safe leaving Pepper in her care. She was very accommodating and understanding. I would definitely recommend her to others.
The best pet sitter. Rosy literally just saved my cat’s life, when she noticed he was not his usual self, took him to the vet, where they identified he had a urinary blockage and likely just hours to live. How lucky for us that Rosy was caring for our animals and so observant. Thank you, forever. 🌟🌟🌟🌟🌟
Absolutely recommend Rebeca! You can tell she really cares about dogs and loves what she does. My dog Snoopy has anxiety & is very shy at first but he felt at ease with her as soon as he met her during the meet and greet. She was so gentle, patient & sweet with him right away. I felt completely at ease knowing he was in such caring hands. I will def be booking with her again!
Kaitlin was very caring and attentive to our indoor/outdoor cats! She was able to connect with them quickly- even our very shy female- and made sure they had all they needed. She is very responsive and reliable, providing regular updates and quick feedback to any questions.
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 pets like family
1. Search
Browse profiles of sitters near you who offer pet 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 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 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 12,518 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:
- 91% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% 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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