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.
“Because of Sarah’s kind demeanor and professionalism, my trip out of town was much more relaxing. I was a little nervous about my dogs and cat not knowing the person who was going to be taking care of them, but Sarah eased that worry by scheduling a meet a greet prior to my leaving town. She made the process so easy and my animals automatically knew she was a friend. Thank you so much Sarah!”
“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”
“Taylor did a meet and greet before our booking. We enjoyed getting pics and updates on our dog's activites while we were away. She went the extra mile to bring in our mail. Would for sure rebook with Taylor!”
About: I’ve had a passion for animals since I was a little girl. I get along with all my neighbors’ dogs and my neighbors rely on me to take care of them some times. My old roommate has a golden retriever and I love taking care of him, giving him a bath and walking him. I have two cats at home and I even taught them some tricks! I’m currently working part time only on Mondays and Thursdays. So I have lots of free time outside of work taking care of your dogs and playing with them! I also have a car so I can drive to wherever you are and take your dogs for a walk where they are the most comfortable with. I live right next to the bike trail and woods, which is a paradise for dogs! If you have an athletic or active dog, I’ll take your dog running the trails, swimming in the pond, and have all the fun in the outside world! If your dog is less active, I’ll give your dog all the comfort and love at home, making sure they are well fed and entertained.
About: Both of my parents are veterinarians, so I’ve grown up around animals all my life! I have basic animal care skills (walks, feeding, playing) and the extra ones too (animal body language, toxic vs nontoxic foods/materials, giving medication)! I have two cats myself, and have taken care of family and friends’ dogs for years. I’m currently working part time and have a flexible schedule, which means I have plenty of time to play with and visit your pets! I prioritize safety for your pet! I understand that I will be someone unfamiliar coming to the home, and will make sure to let your pet lead the way in our interactions.
About: I’ve had both dogs and cats since I was five years old—life just doesn’t feel complete without a furry friend by my side. After the passing of my own pets, I realized I still have so much love to give. That’s why I’ve found real joy in fostering and caring for other people’s pets—because to me, it’s all about sharing love and companionship. Whether it’s snuggles on the couch, long walks, or playtime (and more playtime!), I’m here to make sure your pet feels safe, loved, and completely at home—whether that’s in your space or mine. I work part-time with a flexible schedule, so chances are good I can match your pet’s routine and work around your calendar—allowing me to spend quality time with your pet when they need it most. When your fur baby is with me—whether in your home or mine—they’re part of the family! I stick to their usual routine, whether that means long walks, zoomies in the yard, or couch snuggles (my personal favorite). I don’t have any pets right now and my children are grown, so when they stay with me it’s a one-on-one hangout—just me and your fur baby getting all the attention they want. In your home, I’ll keep things just the way they like it, with lots of love and playtime mixed in.
“Our 6 month old puppy cuddled up with Revan after only a few minutes and I was convinced she really is the dog whisperer. Our cat came out to see her too! It's very rare that our cat comes out when a new person is in the house. We are excited to have Revan housesit next month and know our babies will be in the best possible care.”
About: I love caring for dogs. I will take good care of your dog in a safe environment. Enjoy playing with the dogs as well. I have dog of my own who is very friendly with other dogs she is an 8 year old schnoodle. She enjoys being around other dogs, but does not bother them in any way. I am responsible with feeding dogs and walking them as well if needed. I also have space if needed for dog to play and sleep. I am flexible with hours from morning, afternoon and nights. Although weekends are more restricted for me and not as much availability. I am very attentive and flexible and I will meet the needs for the care of the dog. Contact me if interested.
About: Throughout my life I have had a wide range of pets. I have had a couple dogs, cats, some rabbits, and a snake at one point. I spent a good part of my youth riding and caring for horses. I love all animals and want to do my best to assist you in caring for your beloved pet. I am currently in the mental health field and would like to walk dogs on the side for extra money and the extra cuteness of course! I will care for your pet however I am instructed to do so, but overall just keeping your pet happy, safe, and occupied for the time you are gone.
About: I have always had a love for animals especially dogs. I’ve had opportunities to train puppies and be around senior dogs. I currently have 1 dog of my own who I rescued during COVID. I work full time during the week. But I am looking to pick up some extra dog walking hours in the evenings and or weekends . When I’m caring for your pet I will care for them as if they were my dog. No need to worry if they’re being giving all the love attention they deserve.
About: Since I was a teen, I've always been the go-to person asked to pet sit for people when they went on vacation. I've done it for 10+ years. I recently graduated from law school in May, and I am currently studying for the BAR. I would love to make some money on the side, caring for your special guys and girls! Currently, I have full availability because my sole focus is studying for the BAR. So I can make myself available at any time day or night! I love animals, and I recognize how much they crave attention, especially when they're missing their owner. I would love to provide that necessary attention in your absence. I will make sure that your place is the same as it was when I got there. With a fresh litter box cleaning for cats.
“My cat received caring and helpful attention from Kara, the cat sitter. Especially when, as she is so friendly, kitty Francine did let her approach! It's the first time ever in this former hoarding victim's life, a stranger was allowed to see, and photograph, Francine! Thank you so much Kara!”
About: Used to have my own dog (also cats when I was younger). Now I love to play with and take care of the pets of my friends, family and neighbors! Excited to care for your animal :) Currently on break for the summer so I have a lot of flexibility when I am in town to go for walks, hang out or extended stay care. I will be respectful of your space and make sure your animal feels comfortable in their environment. Let me know what your pet needs and I will do my best to accommodate.
About: I’ve had dogs in my family since I was in elementary school. I’ve been responsible for things like feeding them, walking them, and taking them out at night and in the morning Right now, my only commitments are on Sunday mornings, when I teach religious school in Deerfield. I’m looking for my next full time job currently, and heard about Rover through word of mouth. I’ll take your dog out first thing in the morning and last thing before bed. I’ll feed them right after they go out in the morning, and before I have dinner myself. I’ll also walk them at least once a day, weather dependent
About: I love making friends with doggies and cats. i love taking picture of them while spoiling them with their favorite toys, treats, couches and so on. I am currently a graduate student at Northwestern University and work part time on digital marketing consulting. I have very flexible schedules and home most of the time. i have a large fenced in backyard and I love taking dogs for a nice long walks! I love spoiling them with all the comfy beds/chairs and treats!
About: I’ve spent some time in high school training service dogs for injured war vets! I also have worked in quite a few doggy day cares! I grew up with dogs and have loved them since infancy! I’m currently working a pretty flexible job allowing me more time to ensure your loved fur babies can be properly taken care of! I have a pretty open weekly routine so I have so much time to put towards pet care! I have 1 dog and 2 cats I care for them by making sure all they’re needs are met between both my cats one’s high energy one’s chill I make sure my high energy girl is played with and stimulated mentally every day, same for my dog we go on long walks twice a day!
About: I've owned two dogs and cared for both from puppyhood through their senior years, so I'm familiar with the different needs that come with each stage of life. My second dog also managed to get into more than a few unexpected situations, which taught me to pay close attention, stay calm, and recognize when something doesn't seem right. In addition to caring for my own dogs, I've dog sat for a number of others, each with their own personalities, routines, and preferences. I know every dog is different, and I enjoy getting to know what makes each one feel comfortable and happy. I treat every dog in my care like they're my own and always do my best to make sure they feel safe, loved, and well cared for while you're away. I currently work at Starbucks as a supervisor. I have semi-flexible hours and given enough notice I can make myself more available. (3 or so weeks) I always work try and work my schedule around yours. I typically work 8 hours a day and can’t usually step away to do a pop in during that time. I always strive to leave your home as you left it and your pups happy to see you arrive home again! If you need me to do house duties while I’m there I will do my best to assist with it.
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?
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 dog sitting
1. Search
Browse profiles of sitters near you who offer dog 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 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 of Dog Sitting in Winnetka on Rover is $21 per visit as of October 2026. Most bookings cost between $14 and $42 per visit. 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 11,571 sitters on Rover offering Dog 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.
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 .
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.
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 .
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:
- 85% of sitters can help with special care needs
- 91% 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.
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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