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 55 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: 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.
“The very very very best. I leave for trips with complete peace of mind that they will love our pets and treat them like we do. We come back to happy, beautifully cared-for animals, every time.”
“Stephen and Donna did an excellent job walking our Great Pyrenees mix several times over a few weeks. You could feel their love for dogs from the moment we met them and they were very communicative and kind throughout the whole process. Our boy enjoyed and looked forward to his walks with them and we would definitely recommend and use their services in the future.”
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 been an animal lover my whole life and have had pets since I was 5 years old. I currently have two cats who I am the primary care giver. My late dog, Mara (a black lab), became diabetic when she was 11. For the last 3 years of her life, I administered her insulin shots twice a day. From March 2019-March 2020, I volunteered at CARE Skokie and have watched friend’s cats and dogs over the years while they were away. Animal welfare means a lot to me and I understand the importance of providing consistent and loving care. I would love to have the opportunity to be of service to you and your four-legged family member(s)! I recently resigned from my job in Wealth Management and am focusing on doing things that are more fulfilling and I love animals. I am currently working part time at a local garden shop and have a flexible schedule that allows me time to tend to your pet(s) as needed! I grew up with a dog and have two cats at home who I am the primary care giver for. I am an advocate for all animals to be well taken care of and understand the importance of their needs being met through consistency and loving care.
“For anyone looking for a sitter go ahead and just hire Jacqueline now! Jacqueline dropped everything to come and meet my cat and then take over watching her for 10 days when our previous sitter cancelled at the very last minute. She truly loves animals and was so happy to take care of my cat! She provided amazing detailed daily feedback on my kitty, was immediately responsive to any messages I sent her, and really just made me feel that my cat was in great hands when I was away. I can’t recommend her more! Absolutely hire her now!”
“Susan was a wonderful cat sitter! She's communicated daily and sent pictures that gave me peace knowing that my furry family was being well cared for while I away. I will be contacting Susan again when I go on my next vacation.”
About: I've always had dogs my whole life. Friends and family can always rely on me to take care of their pets or check in on their pets whenever they are out of town or busy at work. I will feed, walk, and play for however much time is needed. I currently work early mornings but there is someone always at the house to feed, play and keep your furry friends company! My whole day after work is completely open so I can't wait to take care of them. Huge fenced yard as well as a my own pet to play with your furry friend if needed. Plenty of toys to keep them occupied as well as plenty of treats to spoil them.
“Tiffany was able to take on a last minute requests after an emergency medical situation with our previous sitter. Great communication - making sure we are updated on our cat’e welfare and care. I’m glad we gave her a try - and so should you.”
“Brittany did a great job taking care of my cat! She was always on time for her visits and provided detailed updates and pictures after every check-in, which gave me peace of mind while I was away. She was attentive, caring, and made sure my cat was well taken care of and got plenty of love and attention. I really appreciated her communication and reliability. I would definitely recommend Brittany to anyone looking for a trustworthy and caring sitter!”
About: I love animals, I feel connected to them. Pets have been in my heart, life and home since I was 5 years old. I’ve walked dogs for friends, family and for elderly friends. Also, I substitute for my dog-sitter/walker friends on Rover when they aren’t available. I helped breed Yorkies at one point, and helped find them homes. I’ve fostered cats in the past and currently own one :) I am available during the day between 10am and 2pm, Monday through Friday. I work part time before and after that, but I will be as flexible as possible I do have a fenced yard. Also, I am a runner. I can walk or jog with your pup if you’d like the exercise for them.
About: Hi! I'm Megan, and I am a dog lover. :) While I have family members with allergies who have prevented me from having dogs of my own, I have dog sat for 6+ years and have also babysat for families with dogs for 7.5 years. While I didn't grow up with dogs in my own home, I have owned 2 hamsters, 3 guinea pigs, as well as numerous fish throughout my life, starting when I was just 3-years-old! I understand the attentive and diligent care pets need, and I can guarantee I will exceed your expectations! I truly have a love for dogs, and I would love to love and care for your pups! I dream of the day I can own my own golden doodle :) I work a hybrid internship, so I have flexibility with caring for your dogs. My availability also reflects when I can be attentive to caring for your dog(s). :) I will be very diligent when walking/taking care of your dogs by only taking them through safe areas and ensuring that they are out of harm's way.
“I appreciate that Arianna spent the extra time to give our cat Finley the attention he craves when we’re away. She gave him a treat each day and spent time brushing him (his favorite). I also appreciated the photo updates. Thank you Arianna!”
About: Enthusiastic and engergetic dog sitter. I love dogs. I love taking them to dog parks and on long walks in the forest preserve by my house. I've had dogs my whole life and always have taken great care of them to make sure they have a happy and fulfilled life. My most recent dog is a Collie named Buehrle with lots of energy. He loves to go for runs in fields and play with other dogs at the dog beach.
“thanks for taking care of my babies! i literally couldn’t have asked for more; great communicator, lots of pictures, and went above and beyond in terms of caring for them.”
“Rebekah was on time, patient with my anxious doggo even offering to come back later if needed. I appreciated the communication throughout the drop-in visit and the many pet pictures. Pets were left happy.”
“Katelyn took my appointment on very short notice and did an amazing job. She was very accommodating and kept me updated throughout the night while I was out of town at a wedding. I’m very new to leaving my dog with someone and Katelyn made the process very easy for me and did a great job keeping my mind at ease. My dog really liked her and had a great time. I highly recommend booking Katelyn”
The median cost per visit for pet sitting in Winnetka is $20
Pet parents share their Rover experiences - Winnetka
Jiayi was terrific! She kept Me updated with excellent photos of the cats and chores completed, feeding, litter, taking in mail. She was very thorough with daily communication. The Cats are happy and calm and the house is as I left it. I would definitely use her again!
Rosy was great! Both of my cats need pills and one is particularly adept at hiding in general, so we were worried about how he would react. She tried various strategies to get a pill in him, and even though it was unsuccessful in the end, I really appreciated her tenacity. She sent pictures and very reassuring updates after each visit.
Katie did a wonderful job with my kitty! She was very nice and easy to communicate with and followed all instructions with no issues. I really appreciate her going the extra mile to make sure my cat was comfortable and well taken care of. I would absolutely hire Katie again and highly recommend her if you’re looking for a cat sitter!
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.
How to book pet sitting
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 for pet sitting - Winnetka
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winnetka average 6 repeat pet sitting clients
FAQs for Pet Sitting - Winnetka
Frequently asked questions about Rover
The average cost of Pet Sitting in Winnetka is $28 per visit as of October 2026. Most bookings cost between $19 and $39 per visit. On Rover, 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 October 2026, there are 12,072 sitters on Rover offering Pet Sitting across Winnetka. 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.
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 .
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 , 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:
- 85% of sitters can help with special care needs
- 90% can help with giving oral medications or injections
- 94% 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 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 .
sitters on Rover set their own , 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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