Dog Sitting Winnetka
Book a Winnetka dog sitter to watch your dog in your sitter’s home or yours.
Over 9 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 have experience caring for dogs through pet sitting, dog walking, and caring for pets for family, friends, and clients. I’m comfortable with feeding, walks, playtime, and following specific care instructions. I’m reliable, responsible, and treat every pet like my own to ensure they feel safe, happy, and loved while you’re away. I am currently working part-time, which gives me a flexible schedule and plenty of time to care for your pets. I can provide walks, playtime, feeding, cuddles, and lots of attention throughout the day to keep your pet happy and comfortable. Your pet’s safety and happiness are my top priorities. I follow all care instructions, maintain their routine, provide plenty of exercise and attention, and send regular updates so you can have peace of mind while you’re away.
“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: I’ve had dogs my entire life and have extensive hands-on experience caring for dogs of various breeds, sizes, and temperaments. Growing up with dogs has given me a strong understanding of their daily needs, behavior, exercise routines, and overall care. Over the past two years, I’ve also expanded my experience by professionally caring for other families’ dogs, including large breeds. My responsibilities have included walking, feeding, playtime, maintaining routines, providing companionship, and ensuring each dog feels safe, loved, and well cared for. I’m comfortable handling larger dogs with confidence and patience, and I’m committed to providing dependable, attentive care tailored to each pet’s individual needs. I’m currently studying full time. But during the day I have enough time to take care of pets in differents times of the day. I'm looking for pet care in the customers' house. This way I can make sure that the pets are comfortable and safe in the place where they live. Sometimes when they are transferred to another place they can suffer from stress or anxiety
About: I have owned and loved dogs my entire life. I've had Labs (I currently have a Golden/Lab mix named Joey! He has ALL of the Golden retriever energy), Greyhounds (RIP sweet Gloria and Cougar!), Austrailian shepherds, and German shepherds as my own and/or family pets, and am very comfortable with high energy, big breeds. I love giving extra smart dogs some fun mental challenges to keep them occupied, and of course am happy to rub bellies for as long as the dog requests. I love the high energy and silly quirks of smaller dog breeds too! I've house sat and cared for animals off and on for over a decade, but have just recently reactivated my Rover profile and am looking to accept new clients. I work part time as a yoga instructor, and homeschool my kiddos. My schedule is VERY flexible, and I am often able to pick up day-of requests. I've a Type-A scheduler too though, so I love some advanced notice! I can't imagine my life without pets and feel strongly that a home just doesn't feel like a home without pets. I will treat your pets just like a family member, because that's exactly who they are! I love specific requests, and accomodating exactly what your pet is used to so they don't feel lonely or confused.
“Michelle M. is awesome! She was great with our English Mastiffs, managed to help us bathe them despite their hyped-up state. She's very personable and easy to relate to as well. We look forward to having her housesit for us in the future. Thanks, Michelle!”
“Can’t say enough good things about Camila. Quick to respond to my request, flexible to setup a meet and greet, great with the dogs, sent pictures and was very informative about how they were doing and arrived within the agreed upon appointment time. I would absolutely recommend her and use her again.”
“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!”
About: I provide loving, reliable care tailored to your pets needs! With experience in house sitting, dog sitting, and caring for my own fur babies throughout the years, I understand the importance of trust and personalized care. Whether it’s energetic playtime, gentle senior care, or sticking to a routine, I’ll make sure your dog feels safe, happy, and loved while you’re away. As a teacher, my summers and weekends are flexible, giving me plenty of time to provide attentive, loving care for your pup. Whether it’s daily walks, playtime, or overnight stays, I’ll make sure your dog gets the care and attention they deserve! "I provide personalized, attentive care whether in my home or yours! In your home, I ensure your pet sticks to their routine, offering plenty of love, exercise, and companionship. I keep their space clean, follow feeding and medication schedules, and provide regular updates for your peace of mind. If caring for pets in my home, I create a safe, comfortable environment with plenty of playtime, cuddles, and enrichment to keep them happy and relaxed. No matter the setting, your pet’s well-being and happiness are my top priorities.
About: I’ve been around dogs and cats all my life, recently worked with animals as big as horses and cows, to chickens and ducks. Friends and family trust me with their animals! My schedule is currently free, weekdays and weekends and nights! I am willing to work holidays. I will also walk in any type of weather! I have a fenced in backyard, with 2 very friend dogs for yours to play with! I do have crates (if needed) and lots of treats!
About: My house has always been filled with pets! My entire life I have never had less than two pets in the house, currently owning three cats and one dog. Being brought up in a household like this has allowed me to gain natural skills in pet care, with those skills becoming second nature today. Pet care is not something I can consider a job, as it is too much of a personal passion! I’m currently a college student working towards a career in wildlife rehabilitation, hoping to continue caring for animals. I am experienced with pets of all ages and can ensure that your pets will not only be safe and cared for, but loved and cherished as my own! I am currently a college student on summer break, allowing me much availability over the next few months! While I am working one other job, it is part-time and I will remain available on days I am working. I offer services that involve pet care outside of my personal household. Any instructions given to me for the particular household will be thoroughly followed with immense care.
“Leah was prompt with her check in and check out times and continually sent us pictures from each visit and an update as to what she did. On her initial visit to meet our 2 cats, one of our cats was a little moody that day and wasn't interested in meeting Leah. But by the second day Leah told us that that particular cat was her new "bestie". The cats were well cared for and everything was done that was noted to be done.”
“Parisa was an absolute angel. Our beloved pet rabbit became sick while we were out of town, and she immediately stepped in to provide emergency care without hesitation. Her compassion, attentiveness, and genuine love for animals truly saved our little one’s life. We are forever grateful for what she did. she went above and beyond in every way imaginable. It’s rare to find someone as kind and dedicated as Parisa, and we can’t recommend her enough to anyone looking for a trustworthy and caring pet sitter. She’s simply amazing”
“Paige is FANTASTIC! My dogs loved her the minute they met her. She took great care of them and communicates well. I had no worries at all going away and leaving my 2 Danes in her care! She’s definitely added to the top of our pet sitter list!”
“Nancyanne was terrific with our cat Kate while we were away on a long weekend trip. She stopped in as scheduled to check on her and provided us with very cute photos on each visit. It was reassuring to know she was in good hands while were were away. Thank you, Nancyanne!”
The median cost per visit for dog sitting in Winnetka is $20
Dog parents share their Rover experiences - Winnetka
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 Rover works
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet & Greet
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 dog sitting clients
FAQs for Drop-In Visits - Winnetka
Frequently asked questions about Rover
The average cost for Dog Sitting in Winnetka on Rover is $22.2 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 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 July 2026, there are 11,955 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.
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