Dog Sitting Winnetka
Book a Winnetka dog sitter to watch your dog in your sitter’s home or yours.

Over 8 pet parents in Winnetka have booked dog sitting
Winnetka, Find top rated dog 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 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.
About: My daughter and I have been boarding dogs for years and love it, we really focus on one families pet at a time so we give him/her our full love and attention. We will take up to 2 dogs at a time. We love to walk and play with the dogs. We have a large fully enclosed back yard in addition to a park at the end of our block we can walk dogs around a large walking path. We text photos and funny videos of us with your pet. My daughter is off to college this year and this will assist her school fund. We love these dogs as if they were our own. WE love taking care of pets, We love staying active walking and playing with the dogs. We will not take dogs if we do not have time for them. I have an enclosed back yard that is perfect for active dogs to chase birds and have a bit of an area to run free. We do walk the dogs to our local park at the end of our block.
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: 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!
“Jacky went above and beyond with our two dogs while we were gone for a week! One of our dogs got sick right before we left and she was so helpful giving his meds and watching out for his symptoms. I knew they were in great hands. Thanks again!”
About: I have been pet-sitting for 7 years; caring for animals is my passion! My style of sitting is treating every pet as if they’re my own😊🐾 I am currently working a part time job, so I may have certain windows of availability—but I am more than happy to work with you on times :) In my clients home, I will follow all rules and guidelines relating not only to their pet, but also to respecting their space as well.
“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.”

About: Growing up I have always had 3 cats at home and have pet sitted for a little over 5 years! My clients have had a mix of dogs and cats so I have experience with both! I can do drop-in visits in the mornings and evenings to feed them, walk them, etc. But the time frame can vary depending on the pets needs and my work schedule I feed them, play with them, walk them, and change the litter boxes (cats). If any more care is required you can text me if needed!
“Cody is amazing! She took the time to learn my dog’s specific needs and personality, and tailors her interaction with them. Her many years of experience with dogs was evident in the way that she cared for my senior dog’s needs and quirks. Aside from her professionalism (always on time, dependable, reliable, trustworthy), she is passionate about dogs, and my little one absolutely loved her! She went out of her way to make sure that my dog felt safe and happy while I was away, and sent me lots of cute pics. I can’t say enough great things about her. You will love her. I will definitely be rebooking her again!”
About: I love animals. Growing up with pets of all kinds I learned to appreciate them and recognize their needs. I know the importance of bonding with them and find great joy in forming that bond. I did domestic care for four years and my primary job was tending to the animals. I am trustworthy and caring and I will put the needs of your pet first. Every time. I have made pet care my priority. I presently work full time in pet car. I also love pet photography and offer that as a service I am available on a drop-in basis and I can make myself available for overnights and extended stays as well. Whatever you need, don't hesitate to ask. I have cleared my schedule to make myself available to tend to dogs and cats full-time. I will walk your dog or simply hang out with your pet, whichever you need. I will build a trust with you, and your pet will know. I look forward to meeting you. I am very conscientious and responsible. I lost my own dog of 14 years and this has opened the door for me to be able to tend to your dog or cat. I can only offer the same loving care that I showed my own dog.
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.
About: I’ve taken care of dogs since I was a kid. I would care for my neighbors animals when they were out of town. I’ve always loved dogs and have a 7 yr old Labradoodle, Max, that I rescued when he was a four month old puppy. He had escaped from his original owners and was missing for two days. When the police found him, he had been run over by a car. They couldn’t save his leg so he’s a tripod. He doesn’t even know he’s missing a leg. Max loves walks, water, and playing with his best doodle friend, Molly. I also have a lot of experience administering insulin shots for dogs. I would love to care for your fur babies the way I care for mine. I am semi retired and my time is very flexible. I’m available for daily walks or pet sitting. I’ll care for your fur baby exact same way I care for mine. My dog Max is living his best life with me. He receives lots of love, walks, snuggles, and playtime. I would give your dogs the same care and affection.
About: We've had dogs and cats in our family for years and miss hearing the patter of paws! We treat our pets well and enjoy playtimes and grooming dogs. Either my son or I are home to be with your pet. I work part time and my son is here when I work. He is working on his master's in business and loves to walk and play with the dogs. We do not have any pets of our own at present. This is a pet friendly home and yard on a quiet cul de sac. We dog sit other family members pets at time. Dogs are welcome in most rooms of the house.
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.
About: I am a life-long animal lover that turned that love into a career after moving into my home with a fenced yard. I have experience caring for dogs of all shapes, sizes, and temperaments. I purchased my home with my dogs in mind as I've got a fenced yard and I wanted to make sure that they had plenty of room to run around. Your dog will be treated like family while they're staying with me. I have three dogs of my own that range in age from 2 to 12, so no matter what speed your dog likes to go we've got something for them. For anyone little who needs it I've got stairs to get up on furniture. My pup, Lego, LOVES to play and will welcome any playmates with open paws. We've got tons of toys and chews around the house and lots of beds and couches to lounge on if that's what they're into. Other than occasional errands I may need to run, I am home full-time with the dogs. Due to this, the dogs don't have a lot of opportunities to get bored…in fact I have many owners texting me after telling me how tired their dog was after staying here! I try to let the dogs be outside and play to their heart’s content (weather permitting, of course). I started Rover as something to do on the side to spend time with dogs, and it has grown to be a full time gig for me and I couldn’t be happier. Being around dogs is truly what brings me joy--it would be my pleasure to take care of your pup while you're away. WHAT KIND OF DOGS DO BEST HERE? My goal is to let the dogs interact and play as much as possible, so well socialized dogs do best at my house. If your dog prefers to be alone or has aggressive/anxiety-based behaviors, then I may not be the sitter for you. Please keep this in mind as you consider me as a potential dog sitter. I am not for every dog and we want to ensure your dog is comfortable in its environment. Please note that I do foster dogs for Chicago Rescue Authority. Foster dogs will never interact with any guest dogs until they have been fully vetted and thoroughly tested to ensure they can safely interact with the pack. I purchased my home with my dogs in mind as I've got a fenced yard and I wanted to make sure that they had plenty of room to run around. Your dog will be treated like family while they're staying with me. I have three dogs of my own that range in age from 2 to 12, so no matter what speed your dog likes to go we've got something for them. For anyone little who needs it I've got stairs to get up on furniture. My pup, Lego, LOVES to play and will welcome any playmates with open paws. We've got tons of toys and chews around the house and lots of beds and couches to lounge on if that's what they're into.
The median cost per visit for dog sitting in Winnetka is $20
Dog parents share their Rover experiences - Winnetka
Donna and Stephen were absolutely fantastic with Jax! From the moment I left him, I felt completely comfortable knowing he was in such caring and attentive hands. They treated Jax like he was one of their own, and I especially loved receiving pictures throughout his stay. Seeing how happy and comfortable he was gave me such peace of mind and let me know he was being well cared for and having a great time. It means so much to find people you can truly trust with your fur baby, and Donna and Stephen are definitely those people. Jax gives them five paws! 🐾🐾🐾🐾🐾 I would absolutely recommend them and will definitely be using them again. Thank you both for taking such wonderful care of Jax! ❤️

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!

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 dogs like family

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Popular requests for dog sitting - Winnetka
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winnetka average 7 repeat dog sitting clients
FAQs for Dog Sitting - Winnetka
Frequently asked questions about Rover
The average cost for Dog Sitting in Winnetka on Rover is $21.09 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog 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 Dog Sitting. For more information on service fees, click here .
As of September 2026, there are 11,678 sitters on Rover offering Dog 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.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winnetka choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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.
A Meet & Greet is a short introductory meeting between you, your dog, 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winnetka with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
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.
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.








