Dog Sitting in Winnetka
Book a Winnetka dog sitter to watch your dog in your sitter’s home or yours.
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Top rated Winnetka dog sitters
“Helped out very last minute for long term care of 2 cats. Great communication, reliable, and helpful. Great experience and would absolutely recommend Crystal to anyone looking for a pet sitter.”
“Leah was great! It was wonderful to have someone who overthought feeding my boys and making sure they got their medicines. One of my boys is super shy and she took the time to find his hiding spots to check on him and even sat near by to lure him out. My other guy got lots of attention as well. Leah also went beyond cat sitting to water the plants, bring in the mail and brought in the trash cans from the curb.”
About: I have several years of hands-on experience caring for dogs of all ages, sizes, and temperaments. From energetic puppies to senior dogs needing extra patience and care, I tailor my approach to each pet’s needs. I’m confident in handling feeding routines, administering medication, and maintaining a calm, safe environment, whether during walks, playtime, or overnight stays. What sets me apart is my attention to detail and commitment to each pet’s well-being. I treat every dog as if they were my own, ensuring they feel comfortable, engaged, and loved while you’re away. I’m also highly dependable, responsive, and respectful of your home and your pet’s routine. I currently work part-time, which allows me flexible availability to provide quality pet care. I’m available for dog walking and sitting before 4 PM and after 7 PM from Monday to Thursday, and on Fridays & weekends, I’m free before 1 PM and after 5 PM. This schedule ensures I can give your pet focused attention during these times while fitting care reliably into my day. When caring for pets in their own home, I prioritize creating a safe, calm, and comfortable environment that respects their routine and space. Whether I’m walking your dog or staying overnight, I follow all your instructions carefully, from feeding and exercise to medication and playtime. I maintain open communication with you throughout the care period, providing updates and photos to keep you connected. As a dog walker, I always make sure that leashes and harnesses are secure, stay aware of surroundings, and ensure your dog is safe and happy during every outing. For overnight stays, I treat your home with respect and maintain a clean, quiet atmosphere so your pet feels secure and relaxed while you’re away. Your pet’s safety and well-being are my top priorities, and I strive to build trust with both you and your furry friend through responsible, loving care.
“Adam was great! My pup Jax was in great hands. Adam left updates and paid close attention to my pups needs and corky ways. We definitely recommend Adam and will be using him again.”
About: I have spent my entire life surrounded by animals. I have taken care of not only my own but other peoples pets for many years now. I have worked in the veterinary medical field for the last 8 years and have experience in pet first aid and trauma response. I have just finished clinical rotations and currently have a pretty flexible schedule and am available 7 days a week to help take care of your pet. I am comfortable working with any breed or size pet. I have plenty of experience with basic pet care and medication administration. I will provide plenty of updates on how your pet is doing, and will treat them as I would my own pets.
About: I've had dogs my whole life, currently have a big lab/hound mix now. My first job in high school was working at a dog groomer so I have lots of experience with all sorts of dogs. As a bigger dude I have no problem walking big or small dogs. I'm a stay at home Dad so I can make most days and times work as long as the times can be a little flexible. I will care for your dog(s) however you specify. I will be patient and give lots of pets whenever I visit for a drop in or walk.
About: I owned a small dog and a fairly large one (a Rough Collie). I love animals. I want to do dog walking and sitting as my main job. I'm 5'10 and 210 lbs. I'm great with small and medium dogs. I'll take out a large dog who is leash-trained. On rare occasions, I take out extra-large dogs. Pet care will be my main priority. My other work is very flexible. I usually work from home or a cafe. For dog walking, I typically play with dogs. I'm patient, so we can take our time - even if that means sniffing every tree. I usually do dog sitting in the client's home and or yard. Occasionally, I board a small or medium-sized dog in my home. I have a small backyard/patio, which is shown in one of my photos.
About: I’ve been the owner of a pit bull/lab mix for 6 years. My doggie was definitely a trouble maker growing up, so I’m able to handle a lot of stress. I’ve house sat and watched my friends doggies countless times, and they always ask me whenever they need a pet sitter! I love love love doggies so much, so it’ll be amazing if I can get paid while spending time with them! I work 6am-3pm and after that I’m available to walk, baby sit, play with your doggies! I especially love long walks, and playtime with dogs! I always make sure that there’s a trust between me and the doggie first. I don’t want to make the dog overwhelmed so I let them sniff me first, and see how they react around me. If they are a little nervous and scared, I’ll try to ease them in with some treats or some pets. I always want to make sure they feel safe and secure.
About: I have always loved animals of all kinds and have taken care of a wide variety of them throughout my life. I have worked in animal rehabilitation, in a pet store, and in dog daycare. I also have experience training dogs, and can work training into any visit upon request. I am currently home from college for the summer and have very few other commitments, so I am able to focus on your pets and provide them with loving, attentive care around your schedule. I will follow all instructions provided to me and employ my wealth of knowledge to ensure that your pet is safe and looked after. I will be sure to provide the same level of care that you would, so you never have to worry about your pet while you're busy. I am happy to provide updates over text so you know that your pet is well taken care of.
About: I love hanging out with animals! I've been fortunate over the last few years to live with dogs of various ages and watched all kinds of breeds and personalities. I have experience with older dogs and more recently have experience with puppy care/training. I also have a high energy pup with separation anxiety, so plenty of applicable experience to give your furry friend the best care! Currently work flexible hours over the next few months. Typically, I'm more open in the morning but can make it work for you an your pup! Currently live in a dog friendly space in a walkable area with plenty of fun routes to take! I'm very attentive of dogs needs and always looking to read their energy. After recent experience with my puppy, I always have eyes on dogs to ensure they're happy while not getting into trouble!
“Marta was very good with Willow. She was able to accommodate us last minute and was very flexible when we needed to add a day. She took excellent care of her and kept us up to date on how she was doing.”
“Amazing!! Lauren watched our house for a week, picked up our mail, and fed and walked our dog everyday. She put away our groceries that were delivered to our home. We love Lauren!! We are so thankful for her flexibility and she eased our stress knowing our dog and home were taken care of while we were away. I hope you will choose her because she is amazing!!”
About: I've been fostering kittens and working with dogs for more than 10 years, and am currently taking a gap year before getting my Masters in Animal Studies! I have experience in everything from potty training puppies to giving elderly animals multiple types of medication, and I love dogs and cats of all shapes and sizes. I currently have a 5.5 year old Lab/Basset Hound mix named Betty and we walk around 3-5 miles everyday, so please let me know if your dog would be interested in a (discounted) group walk! I'm currently taking a gap year so my schedule is very available as of now. Please let me know if you would like to set up a routine time/schedule in advance so that I keep the same time available! I have experience in caring for dogs and cats between 5 - 145 pounds, and from ages ranging ranging from 6 weeks to 19 years old. I have also fostered more than 50 kittens, so I know that each and every animal has their own personality and quirks. Please let me know if there is anything I can do to make you or your dog/cat more comfortable so that they have an enjoyable time!
About: I am and always have been an animal lover. I am 45 years old and have always had a dog that I have been lucky enough to take care of throughout my entire life. I truly believe that animals make humans better people and that we can continually learn so much from them. I currently work part time as a piano teacher, and so pet care offers me flexibility as well as gives me the opportunity to take care of animals-something that is dear to my heart. I offer treats and allow my furry friends the freedom to explore my house as they please. They are more than welcome to hop up on my couch or bed if they like. And, if they have a favorite bed they like to use and bring along, they are more than welcome to do that too. Whatever makes them feel most comfortable.
About: I’ve taken care of dogs since I was ten, led a dog rescue, managed a dog hotel, and befriended dogs of every shape and size. As a father of both dogs and children, you will appreciate my experience, patience, and diligence. My schedule revolves around my clients and their dogs. You can expect the utmost professionalism and attention to your dog and their needs, big or small. When I come to your home you can trust both your dog(s) and house are well-protected. I am a veteran with Federal Trusted status and your neighbor. I have worked with dogs of all sizes, ages, and needs—in many settings.
“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!”
About: I have had a dog for over 10 years. I take care of them all the time I used to walk dogs and I foster cats. I only go to school from 7 AM till 2 PM. But anytime after that, I’d be happy to take care of dogs and provide excellent care! Well in a client’s home. I would respect anything in their house, I would ensure a dog is able to get physical activity and its needs as well.
“Anna took care of my two pups while I was out of town. They are 14 and 11, so it made us feel much more at east to know they were comfortable in their own home in Anna's care. She communicated with us regularly and sent photos of the pups enjoying their meals. Anna even took in packages for me and kept an eye on the house. We would definitely use her again and highly recommend her to anyone.”
Loving dog sitters in your neighborhood
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Crystal P.
“Helped out very last minute for long term care of 2 cats. Great communication, reliable, and helpful. Great experience and would absolutely recommend Crystal to anyone looking for a pet sitter.”
Leah G.Star Sitter
“Leah was great! It was wonderful to have someone who overthought feeding my boys and making sure they got their medicines. One of my boys is super shy and she took the time to find his hiding spots to check on him and even sat near by to lure him out. My other guy got lots of attention as well. Leah also went beyond cat sitting to water the plants, bring in the mail and brought in the trash cans from the curb.”
Alexa D.
“I cannot recommend Alexa enough as a pet caregiver. From the moment we met her, it was clear that she has a genuine love for animals and a natural ability to connect with them. She took the time to learn about my dog’s unique personality, preferences, and routines, which immediately put me at ease. My dog can be a bit shy around new people, but he warmed up to Alexa within minutes, something that doesn’t happen often. Alexa is not only incredibly loving, but she’s also very responsible and detail-oriented. She followed all of my instructions perfectly, from feeding times and medications to play routines and bedtime rituals. I felt 100% confident that my dog was safe and happy in her care.”
Adam H.Star Sitter
“Adam was great! My pup Jax was in great hands. Adam left updates and paid close attention to my pups needs and corky ways. We definitely recommend Adam and will be using him again.”
Jacob B.
“It took about 5 minutes for my fur babies to connect to Jacob in ways that not very many ppl can. Even my big ole grumpy Labsky tried to sit in his lap!! He has a genuine gift of empathy and special love for all creatures, great and small!”
Suzanne & Benjamin G.
“We so appreciate Suzie and Ben! They took great care of Lucy and even braved the foul weather to make sure our pets and home were safe. Thank you.”
Colin K.
About: I've had dogs my whole life, currently have a big lab/hound mix now. My first job in high school was working at a dog groomer so I have lots of experience with all sorts of dogs. As a bigger dude I have no problem walking big or small dogs. I'm a stay at home Dad so I can make most days and times work as long as the times can be a little flexible. I will care for your dog(s) however you specify. I will be patient and give lots of pets whenever I visit for a drop in or walk.
Megan D.
“My cats love Megan! She is a spectacular cat sitter. She is SO attentive to them. She's very creative and makes up the funniest games. My cats are a year old, so still kittens. One is friendly and the other one is timid. She tends to hide from strangers, even my Mom. By the second time Megan came to sit for me, my shy cat was out from under the bed to greet her! They both like to be where "Auntie Megan (Midge)" is. The real proof of her cat watching talents is when I get home from a week long trip. In the past my Mom would come over twice a day to feed them and play with the fishing poles. Before using Megan, when I would arrive home, my cats were almost unhinged. They would be all over me and at bedtime try to sleep on my face. It would take a couple of days for them to relax again. Now that I have Megan sleep over, the cats are SO RELAXED & CHILL. It's 180 degree difference. They sleep with Megan...a true test, and cuddle with her. The difference in their contentment is really obvious. More than my cats liking her, I can tell she really enjoys hanging out with them. She does some remote work while there, but my fur babies were her priority. When they walk over her laptop keyboard, she doesn't mind. They are playful adolescents. She even brought them some new mouse toys. Also, she's more into tech than I am. She introduced them to Cat TV and cat iPad games. I liked the daily photos she sent. Megan offers a very high end and loving experience for your cats. I highly recommend.”
Marcus A.
“Marcus is hands-down one of the few people we trust with our dog, Sam — and that’s saying something, because Sam is family. He’s not just a sitter, he’s Sam’s uncle, and treats him with the same love, attention, and structure that we do. Whether it’s a weekend trip or a long stay while we were overseas, Marcus has always gone above and beyond. He keeps Sam safe, happy, well-fed, and even a little spoiled (in the best way). If you’re looking for someone who takes pet care seriously and truly bonds with your animal, Marcus is the guy. Couldn’t recommend him more.”
Sadie D.
“Great with our cat!”
Grayson N.
“Grayson has looked after my cat multiple times and pays so much attention to detail when it comes to her! She has very specific dietary needs and they are always prepared for anything that I’ve needed. They are also so friendly with all animals and so excited to get to know them! I’d recommend Grayson to anyone and will keep coming to them for anything to do with my cat!”
Paul H.
“Paul is the best of the best when it comes to caring for furry friends! He knows how to deal with all different kinds of dogs. He always has a calm, steady energy no matter what kind of energy the animals around him have. He knows how to meet dogs wherever they are, and has experience with issues like separation anxiety, reactiveness, and high energy. Can’t recommend him enough!”
Marta L.
“Marta was very good with Willow. She was able to accommodate us last minute and was very flexible when we needed to add a day. She took excellent care of her and kept us up to date on how she was doing.”
Lauren & Lauren P.Star Sitter
“Amazing!! Lauren watched our house for a week, picked up our mail, and fed and walked our dog everyday. She put away our groceries that were delivered to our home. We love Lauren!! We are so thankful for her flexibility and she eased our stress knowing our dog and home were taken care of while we were away. I hope you will choose her because she is amazing!!”
Spencer K.
“I’ve never met anyone who loves animals more than Spencer. He is kind and responsible and is entirely focused on my dog and how she is feeling every minute that he is around her. He is punctual and a standup person in every regard. He takes the time to really know your pet and their special needs and wants and will do everything in his power to ensure that they are comfortable and happy, whether it is pet sitting or simply just taking your sweet dog for a walk. You will not find a better caregiver for cats or dogs than Spencer!”
Katie T.
“I have known Katie for over 20 years and have seen her work throughout multiple environments. She is selfless, honest, and trusting of others. She has gobs of energy and natural sense of grit and tenacity. She has always been a huge animal lover!! If she was a dog she’d be a golden retriever!No doubt you will be greeted with a sense of genuine love the moment you met Katie.”
Andrew K.
“Andrew has been caring for my rescue dog for the last 3 years. Whether I’m at work or out of town, I know my dog is safe, cared for, getting lots of belly rubs, and is in the best hands. I highly recommend Andrew for his trustworthiness, flexibility, and deep understanding of my dog’s needs. Knowing that I can count on Andrew to provide personalized care brings me piece of mind. If you’re looking for someone who will treat your dog like family, I highly recommend the Andrew.”
Nancyanne S.Star Sitter
“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!”
Vivien N.
About: I have had a dog for over 10 years. I take care of them all the time I used to walk dogs and I foster cats. I only go to school from 7 AM till 2 PM. But anytime after that, I’d be happy to take care of dogs and provide excellent care! Well in a client’s home. I would respect anything in their house, I would ensure a dog is able to get physical activity and its needs as well.
Anna D.
“Anna took care of my two pups while I was out of town. They are 14 and 11, so it made us feel much more at east to know they were comfortable in their own home in Anna's care. She communicated with us regularly and sent photos of the pups enjoying their meals. Anna even took in packages for me and kept an eye on the house. We would definitely use her again and highly recommend her to anyone.”
Winnetka dog parents share their Rover experiences
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Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Winnetka.
Rover makes it easy to find Winnetka dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
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