House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 118 pet parents in Winnetka have booked house sitting
Winnetka, Find top rated house sitting
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Jeni is a talented, trusted, handler. She is kind, patient, punctual, honest, friendly, fun, and extremely loving. I can’t possibly express how grateful I am to have Jeni help me with my precious dogs. Her expertise, patience and knowledge have added so much to their lives. They both enjoy-walks, playtime, socialization. My dogs, Brutus (6 year old male Pekingese) and Rambo (1 year old male pug mix, rescue, are thrilled when Jeni comes to take them for their walks, and play dates. Rambo is very shy and panicky. Jeni takes as much time as needed to let Rambo settle which is within seconds. Brutus loves everybody so he and Rambo enjoy their time with Jeni tremendously. Highly, highly, recommend Jeni. I welcome any questions.”
“Oh my gosh, she saved the day! We have a new puppy, but have some event we couldn’t get out of.. I needed an extra early morning request.., she said no problem, then I had to change it to an even earlier time, And she said no problem! She came on time.. sent pics.. couldn’t be more happier! Will definitely use her again!!”
About: I have about 7 years of pet handling experience from my own animals to volunteering at animal shelters in LA. I have worked with dogs and cats of all ages, from puppies to seniors. I have gained experience from my own dogs, one of which was blind and deaf. With over 250 hours volunteering at my local city animal shelter, I gained additional experience caring for cats, dogs, rabbits, hamsters, and guinea pigs. I cannot wait to meet your furry friend! I currently have a very flexible schedule. I am usually busy on the weekends, but I could make myself free if I am given enough notice. When caring for a client’s pet, safety is very important to me. Following the owner’s rules and ensuring your pet is cared for and loved while you are away is my number one priority :)
About: My family has owned dogs and cats my entire life. I don’t think there has been a single day in my life where I didn’t own a pet or have responsibility for one. Including the Marines under my charge. Animals. Seriously, though… Pets love me. I am also a firm believer in following instructions to a T. People are often surprised when I ask to meet their dog, they tell me that the dog is skittish or afraid, and then the dog walks slowly up to me like they’ve known me forever and then we’re best friends. I feed my two cats, Chief and Cosmos, daily at 8am and 8pm. Cosmos requires special dietary food, so my wife and I bought chip-specific feeders for each cat. I also make sure they stay physical with my fishing rod toys, as well as ensure clean facilities for the… you know. It all comes down to showing them love, providing for them, and protecting them. I treat my two cats like they were my own kids. We don’t deserve their love if we can’t give it to them. It’s inhumane.
“Madelyn is now our 4-mo-old puppy's favorite person! She gave up her Thanksgiving to stay with Ziggy at our house, but it wasn't just a "stay." Madelyn played with her and give her so much love and attention. It was just what Ziggy needed and we were so happy to trust her with our puppy! We're also very happy that Madelyn will be coming back to stay with Ziggy again in a couple of weeks. Thank you, Madelyn!”
“Shanneal is a fantastic sitter - she took care of our two puppers, one of whom can be challenging and needs some specific care, for a couple nights at our house. She sent lots of pictures and did a great job making sure the doggies were happy. Highly recommend!”
“Alondra was great. She took excellent care of my dogs and my home, and followed all instructions. My dogs love her, including my picky chi-pug that usually is a bit more standoffish. I can tell she give them lots of attention and love!”
“She was fabulous. Very sweet and took great care of our little puppy. Even right after his neuter surgery. She took photos and videos throughout the night. Very polite.”
“Kimberly was amazing!! I highly recommend her for your home and pet sitting needs. She is extremely communicative - always answers my messages right away and sends lots of photos and videos. Kimberly is flexible and easy to work with. She's friendly and my pets took a liking to her right away! I was very nervous about leaving my babies (2 dogs and 2 cats) with a stranger, but her work ethic and my happy animals made it much easier. Thank you, Kimberly! <3”
“Yana was amazing!! She watched our dog for 5 days in our home and did an amazing job caring for her. I think our dog may be sad to have us home and missing Yana! She sent lots of really cute pictures and videos too! We will be repeat customers for sure!!”
“Amanda was great with our dog. She sent us photo updates frequently and took amazing care of our fuzzy son. We will call her every time we need support and supervision for our dog!”
About: Hey, I’m Anthony! I’ve been around animals since I was born. Grew up on a mini farm and took care of countless of dogs, as well as cats. I actually have a Siamese cat! I’ve always felt so connected with animals my entire life and most (if not all) pets of friends/family love me :) I’ve also watched a lot of pets in my life from time to time, whether it’s for a friend, neighbor, or family member. I work part-time at the moment and I have a lot of time on my hands, aside from work and occasional hobbies. My work schedule is given out a month in advance, so I always know when I’m available in the future and when I’m not. I’m very good with respecting the boundaries of animals and providing the care that they need. Your animal needs a lot of playtime? I got that covered. Your animal needs company but is more on the shy side? Got it, we can just hang out! Let me know what is needed for your pet, how their usual day looks, and I’ll be more than happy to put my all into caring for them
“Larry was great with Pringle. He is very professional, punctual and knowledgeable about dogs. He took great care of Pringle while I away at work and made sure she got lots of attention. It’s clear he really understands and loves working with dogs. I highly recommend.”
“Gillian takes great care of Pringle while I’m at work, and I really appreciate how punctual and responsive she is. I feel at ease knowing Pringle is in good hands, and I definitely plan to be a regular client!”
“We loved Caitlan and our little Mila was so happy. Thank you Caitlan. We came back from our trip and it was clear Mila was so comfortable and happy with your presence. We really appreciated the peace of mind that Mila was a loving hands.”
About: I have 3 dogs at home, two small and one large. I have had dogs all my life and I am comfortable with dogs of all breeds and sizes! I understand the importance of the first time meeting a dog and will be patient until they feel comfortable around me. I have worked with rescues before saving dogs from the streets which is where I learned a lot of my dog skills as well. I love my walks with my dogs and would love to walk yours! I do currently work full time but I am available after 5:00 PM Monday - Friday and all day on the weekends. I hope to get to meet your dog or dogs soon! I currently work full-time but am available for evening walks after 5 PM on Monday - Friday. On the weekends, I am available all day! I have experience dog sitting and always follow the instructions the owner has left for me. I am a guest in the home and always make sure I am on top of all my duties. I triple check everything is the way it should be prior to heading out the door to ensure the comfort and safety of my clients pet.
“We had a great experience with Geena. She took excellent care of both of our Labradors, Pilón and Clark. Clark is a young, energetic puppy with plenty of antics, and she handled him very well. It was clear that she knew how to work with dogs and how to manage his energy and enthusiasm appropriately. She also did a great job with Pilón, making sure both dogs were well looked after and had plenty of playtime and interaction. We felt confident leaving them in her care and appreciated her professionalism and experience. We would happily trust her with our dogs again and highly recommend her to anyone looking for a knowledgeable and reliable pet sitter.”
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
Yana is the best! She has helped take care of my dog many times and is consistently so amazing. She is very attentive to my dog’s well being and is a great problem solver too. She watches out to make sure my dog doesn’t eat random things during walks and thinks about the little things like the best time for his walk depending on how hot the pavement might be. When Yana is with my dog, I know he will be cared for so well!
We highly recommend IULIIA to anyone who needs a wonderful dog sitter! IULIIA watched our dog Molly, for 2 days and stayed overnight at our house. She did an amazing job taking care of everything. She made sure Molly was eel-fed and took her in many great walks. We loved that IULIIA consistently sent us pictures of Molly on her walks and relaxing. It gave us total piece of mind while we were away. On top of that, she kept our house completely clean and tidy. We look forward to having. IULIIA help us again in the future. If you want a trustworthy and caring sitter, IULIIA is the perfect choice!!
Samantha took wonderful care of Morgan, and I couldn't be happier with the experience. She was reliable, professional, and clearly has a genuine love for animals. Throughout the booking, she provided updates and gave me peace of mind knowing Morgan was in excellent hands. When I returned, Morgan was happy, well cared for, and clearly comfortable with Samantha. It is not always easy to find someone you can trust with a beloved pet, but Samantha exceeded my expectations. I would gladly book with her again and highly recommend her to anyone looking for a caring, responsible, and attentive sitter. Thank you, Samantha, for taking such great care of Morgan!
We had a great experience with Geena. She took excellent care of both of our Labradors, Pilón and Clark. Clark is a young, energetic puppy with plenty of antics, and she handled him very well. It was clear that she knew how to work with dogs and how to manage his energy and enthusiasm appropriately. She also did a great job with Pilón, making sure both dogs were well looked after and had plenty of playtime and interaction. We felt confident leaving them in her care and appreciated her professionalism and experience. We would happily trust her with our dogs again and highly recommend her to anyone looking for a knowledgeable and reliable pet sitter.
I appreciated Emily’s observational skills and calm response to my dog being sick while I was gone. She took good care of her and used good common sense in caring for our dog. Our dog was happy and seemed fully recovered when we returned home. The house was clean and she went beyond to make sure everything was back to normal when we returned. Thank you.
Jesse was such a great help to me in taking care of my dog when I was setting up a party. My dog was a bit anxious and overstimulated from all my running around while doing party prep and Jesse helped calm him with cuddles and reassurance. It was a relief to not have to worry about my dog during my party because I knew he was in great hands.
Bouvier was above and beyond communicative and caring of our 2 senior Golden Retrievers, one with medical needs and the other that developed a medical need while we were gone. We felt in the loop the entire time although we were a Continent away. She took over sitting in between another sitter’s stay and was more than willing to communicate personally with her about the status of the pups. We are grateful to Bouvier and look forward to having her our pups in the future.
Taylor is amazing. She was wonderful with our dogs, who she willingly got to know prior to our trip. They immediately bonded with her, even tho one of our dogs is usually slow to connect with new people. She is super responsible and always communicated with us on a daily basis while we were gone. She also took good care of our home and plants. We highly recommend Taylor!
This is our second time using Emily and she is just fantastic! I cannot recommend her enough, she is so caring and thoughtful and provides such excellent care for our fur baby. She sends daily updates and pictures and also took great care of the house since we had her stay at the house for the duration of our vacation as well. Highly trustworthy and responsible, we would continue to use her again every time!
Cynthia watched my dog, Rocco, at my hotel while my husband and I went to dinner and a concert. She was very flexible about coming to our hotel. Cynthia had great communication and made me feel reassured that Rocco was in good hands. She sent texts and photos throughout the night. She took Rocco for a couple walks and fed him dinner. I would definitely recommend her others and will select her again the next time we are in Las Vegas.
Sanaz took wonderful care of our two dogs and two cats while our family was away on vacation. Her communication was always prompt whenever we had a question or wanted to check in. She sent several photos / videos each day and helped administer medication for our cat. I definitely recommend Sanaz as a trustworthy and caring pet / house sitter.
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 house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. 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 3 repeat house sitting clients
FAQs for House Sitting - Winnetka
Frequently asked questions about Rover
The average cost for House Sitting in Winnetka on Rover is $94.35 per night (as of June 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .
As of June 2026, there are 11,887 sitters on Rover offering House Sitting across Winnetka. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winnetka walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Winnetka maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
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!
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.
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 .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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.
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
- 94% can help with giving oral medications or injections
- 97% 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.
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