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.
“Donna is a treasure. She and her husband Stephen work together and took excellent, loving care of our two cats and one dog. They are always on time, truly arm to love their jobs, and send warm, funny photos of our creatures every day. I felt 100% at peace knowing our three pets were in such good hands. Highly recommend Donna and Stephen!”
“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: 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!
“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!”
“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 have been around dogs most of my life. In my life time I had 5 dogs in my house hold but not all at once. I watched my brother German shepherd on multiple occasions and walked many dogs for my neighbors. I also volunteer at the local animal shelter to help them walk and foster dogs too! Can’t wait to meet your pet!! I can walk your dog anytime during the week and weekends, but prefer mornings or afternoons. I can also dog sit for any day during the week and weekends I have dealt with multiple dogs in my life time so I know how to respond in an emergency occasion. I can crate a dog if you need me to.
“Tiffany checked in on my cat, Tofu, while I was gone on a week long trip. She was very communicative and sent lots of cute pics. She brought an issue with our automatic feeder to our attention and went above and beyond to help us trouble shoot the issue. Tofu loved Tiffany and we will be booking her again in the future”
“Lucy went above & beyond, per usual. So thankful to have found her to care for my cats while i’m out of town. She’s so good with them and takes the time to give them both adequate attention and play time. She always communicates and really puts my mind at ease while i’m away knowing my babies are in good hands.”
About: I’m a passionate, reliable pet caregiver with over 10 years of hands-on experience caring for animals. I grew up surrounded by pets and have turned that lifelong love into a career, working with pet families, in pet retail at stores. I understand that every pet has a different personality, routine, and comfort level. Whether your dog loves long walks and playtime or prefers a calm, patient companion, I’ll provide attentive, loving care and treat them like part of my own family. I have a lot of spare time on my hands so I could use that time to care for your pet! I am your pet Nannie around the corner. I have experience dog walking, so I understand how it goes. I also have lots of experience playing with pets. I have a huge passion for pets
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.
About: I grew up with many pets so i’ve been taking care of them since I was very young. I’ve been dog and cat sitting for others for about 4 years now from all different ages ranging from a puppy to an elderly dog. I have a rabbit so Id be happy to rabbit sit! 🐰 I’ve also taken care of a bearded dragon! I’ve administered medication when needed such as insulin to dogs. Pet sitting fits into my daily routine through out the week from the morning time and afternoon time as well. I’m also free on weekends! I create a comfortable and loving environment in owners home so that your pet doesn’t get stressed while away. I keep their normal routine with feedings and walkings as well.
About: I’ve cared for dogs since our family fostered a neighbor’s pup when I was 8 years old. Since then, in my multi-dog household, I have successfully cared for, trained, and housebroken puppies as well as cared for senior dogs. I have extensive experience training and handling reactive and anxious dogs (medium & large breeds), including handling multiple at the same time. I’ve been relied on my neighbors, family, and friends to care for their beloved dogs and cats for many years. I am a warm and compassionate experienced pet owner who is used to caring for dogs of all sizes, ages, and temperaments. I currently do not work a 9-5 job, so I have lots of flexibility and time to spend caring for pets. I am available for dog walking as well as house sitting and pop-in playtime. ** Though I cannot board a pet in my own home, I am more than happy to spend lots of time with your pet to keep them company as well as playtime with my two dogs to keep them company if desired. I can provide a regular walk schedule on weekdays and weekends. I am available to house sit to keep your dog’s schedule and environment as consistent as needed. **
About: From zoos to animal shelters to animal hospitals, I’ve worked with all animals and I just can’t get enough with them! Whatever your pets needs, basic and specials, they will be in good hands with my excellent service, attention to detail, and reliability. I split time between the Evanston/Wilmette area and Des Plaines so let me know what you need and I’ll let you know if it’s feasible depending on the service! I work full time at an animal hospital. I rotate Saturdays and Mondays, working a morning shift one day and the other off. T-FR full 8 hour days. I have had plenty of success in petsitting with this schedule. If the gig is close enough to work, I can do a midday visit. If the gig is farther from work, then I will not do a midday visit. Keep this in mind when booking if your dogs need three walks a day. I stay overnight no problem! With dog walking or pet checkins, I will do them whenever fits with my schedule! Evenings and weekends are pretty much open. I make sure to keep a very clean space so that pets can’t get into anything, and I leave your home looking as though no one was even there. I always double check doors and fences and gates. I do like to brainstorm pet-safe enrichment for them too (comes from my zoo background). I keep their food and water bowls clean, and for dogs we do a lot of walks. 3-4 a day. If allowed, I like to take dogs for field trips like to forest preserves and dog beaches for extra exercise and a change of scenery. For nervous cats, I let them come to me. Normally with time they get a little more comfortable but I won’t force it. I send lots of video and photo updates to pet owners.
“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.”
About: I’ve had cats and dogs throughout my life and I have always felt a strong connection and kindness to animals. I have done petsitting for dogs, cats, and even a leopard gecko before! I have one cat who is 17 years old. His brother was the same age and passed away earlier this year. I had a dog that lived to about 15 and I lost him several years ago, so I have experience with taking care of senior pets and the process of loss. Taking care of pets is something I love doing! I work as a mental health therapist, with most of my shifts from 3pm-8pm on weekdays. I sometimes have meetings in mid-morning. With my job, there is tremendous flexibility due to constant shifts in my caseload and clients cancelling appointments. I am also in charge of my own schedule. Generally, I will be most available in the morning and afternoon for pet care. Weekend availability may fluctuate depending on my plans. I will happily follow your instructions and preferences regarding care for your pet, and I would love to send you pictures and updates! I appreciate it when my own cat-sitter does that for me, so I know you probably do too.
About: I have had cats, dogs, and fish for the past 15 years. I have boarded, walked, and sat many animals including the ones listed above. I have also done feedings and administering medications. I always like to get detailed notes and a walk through of the care you need so the pets are well taken care of throughout my time with them. I am currently open to any times and days. I am in school and am doing it completely online and asynchronous. I can work with you separately to figure out the best schedule. I am always wanting a walk through and detailed sheet of paper describing schedules and everything I need to know. I will also send frequent updates including pictures. I have administered medications before and ask to be shown how to administer so they don’t miss a day.
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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