House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 188 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 had many pets of all kinds. I love them all. As well as my own pets I have experience with other animals from volunteering at the West Valley Animal shelter as well as pet sitting for family and friends. I am very passionate about animal welfare. I’m happy to help with feeding, walks, playtime, cuddles, and just keeping them company. My goal is to make sure your pets feel safe, comfortable and loved while you’re away, giving you peace of mind they’re in good hands. I am currently not working so my schedule is very flexible. I am available for walks, drop-ins, and pet sitting. I love to hang out with my own pets and would love to hang out with yours too! I have two dogs, one cat, and two birds. The dogs and cat have access to a doggy/cat dog that leads to the back yard which is fenced in.
“Ariana was amazing with our two pups! She is very kind & sweet. Amazing energy & the pups felt right at home with her. We felt very comfortable leaving her with the dogs and taking care of our home while we were away. We will definitely be using her as our pet sitter for all of our needs in the future! ?”
“Could not ask for a sweeter kinder more knowledgeable sitter - it was a joy to have Julianna here and can’t wait for her to come back - our husky took to her the minute she wakes in the door !”
“Sanaz is absolutely wonderful! Milo and especially Atlas adore her! They snuggle right up and are completely attached whenever she’s around. It’s clear how much love and comfort she brings them. I’ve already booked her again! She is truly wonderful.”
“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!”
“Yana is so lovely! She talks to my dog, which he loves and gives him lots of cuddles. Very caring and clearly loves taking care of dogs, which makes all the difference. I feel comfortable with her taking care of my dog.”
“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.”
“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!”
About: My passion for pups began by caring for dogs of family and friends, into raising two silly, energetic, dachshund boys of my own! I know firsthand how hard it can be to leave your furry family members behind. This is why I treat every animal in my care with the same unconditional love, patience, and attention I would want someone to give my boys. Over the years, I’ve cared for dogs of every background and breed including tiny Chihuahuas, Yorkies, and Pugs to high-energy Boxers and German Shepherds. No matter their unique personality, I adapt quickly to what makes them feel happy and safe. When booking with me, you can count on Schedule & Routine Maintenance (e.g., following your exact schedule for meals, walks, medication, and playtime so your pup stays relaxed and happy), Warm and Clear Communication (e.g., sending regular updates, photos, and clear check-ins so you always know how your pup is doing), Cleanliness & Organization (e.g., keeping your home clean, tidy, and organized while managing your pup’s living areas and supplies, and Dependability & Trust (e.g., showing up on time, respecting your instructions, and providing consistent, dependable care you can count on every single time). Thank you for stopping by my profile! Feel free to message me with any questions or to set up a meet and greet. Looking forward to meeting you and your furry family member 🐾 Managing my own work and school schedule gives me complete flexibility to adapt to you and your pup’s needs! Whether that be mid-day drop-ins, flexible walk times, or even occasional overnight care. In your home, I prioritize safety, routines, and cleanliness. Whether house sitting, dog sitting, or a quick drop-in, I’ll make sure to follow routines (e.g., feeding schedules, medication needs, and favorite walk routes to ensure your pup feels safe and comfortable), to respect your space (e.g., making sure doors and gates are securely locked, keeping keys safe, and ensuring your privacy every step of the way), and keeping things neat (e.g., clean up after feeding time, handle potty duty right away, and make sure you come home to a space just as clean and cozy as you left it).
“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!”
“Great at communicating, sending photos and videos. There was one hiccup. In our opinion, best way to understand how good someone is is to see how they react to a situation. She was brilliant, organized and effective. Left the house beautiful and the pets happy. Will def use her services moving forward.”
“Diego was great! He came by a few days before to meet my pet Paco. They bonded right away! He took him out on long walks and was flexible with times I needed him. I will definitely be using Diego again!”
“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.”
“After our meet and great, I felt comfortable leaving my baby George an 8 year old spoiled sweetie with Helen but throughout the week each time I heard from her I was more and more relieved to know what good hands he was in. I am happy to give Helen a five star rating (out of five.) Thank you so much Helen!”
About: I have been an animal lover my entire life. I got my first pet at age 4 and have been taking care of cats and dogs ever since. I currently own 3 cats that are keeping me on my toes. I have experience administering medications when took care of my diabetic cat. I'm currently unemployed, so you have my undivided attention. I'm hoping to make pet sitting my next full time gig. I currently have full availability I currently live in a 2 BR apartment in a gated community, with a dedicated dog walking area. I will gladly let your dogs out in your yard, if that's what you're comfortable with or walk your doggo in his/her favorite stomping grounds. I'm totally flexible.
“Larry was an excellent dog sitter for our pup. Our dog is a COVID dog and used to being with someone 24/7. Larry stayed at our house and walked, played and kept our pup company. He was able to bond with Mozzi the first day. We came home to a clean house and a very happy dog. We would definitely hire Larry again. So glad we found him on rover.com.”
About: Ever since I was born, I’ve had a dog in my life. I’ve cared for dogs for as long as I can remember. All of my dogs have lived long lives and were cared for, loved, and spoiled. Dogs are my passion. I’m very intuitive when it comes to dogs needs and can sense when they are requiring extra care. I make sure water bowls are clean no film in the bowl and my dogs get filtered water, if your dogs are in my home they will get the same care. I love to take my dogs on long walks, and to visit dog parks. The dog park in my opinion is the happiest place on earth! I will care for your pets as if they were my own children. Attention to detail, and 100% focus on your pets is what I will guarantee. I am excited to meet your beloved pets and witness their unique personalities! I am available every day of the week and any time. Dogs are my passion and I give nothing but love. My schedule is pretty open! I am a home and dog owner so I know how to care for pets and the home properly. I have house sat before and have experience babysitting animals.
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
We had a great experience with Samantha! She was very thorough with our instructions and sent pics and updates during the stay. She was also forthright with us about getting sick before our booking started so we could make an informed decision about whether or not we still wanted to proceed, which we thought was a responsible and classy move.
Yana stayed with my dog at my home for 5 days/4 nights. I am so happy I found her because she is so incredibly wonderful! She was accommodating to my odd traveling schedule, left my house better than she found it, and most importantly my (sometimes anxious) dog was calm and happy with her here. Yana is great at following instructions and she is also very proactive. I was able to relax on my trip because she sent me lovely updates of my dog and I could tell he was comfortable, happy, and very well cared for. I would wholeheartedly recommend Yana.
I could not have asked for a better dog and house sitter. I met Geena and explained what I wanted done with my dogs while I was away for 3 weeks; thier feeding times, walk schedule, sleeping arrangements, etc. I was relived that she was mature, responsibe, and trustworthy. She updated me daily with texts and photos of my (2) dogs whom I missed terribly. She brought in mail and kept the house nice and tidy and controlled the A/C. I was able to travel without worrying as I knew Geena was giving love and attention to my little ones. Without reservation I would hire Geena again !!!
Helen was a wonderful and caring sitter for our kitties. She was responsible, attentive, and an excellent communicator throughout her sitting. We felt very comfortable knowing our cats were in such good hands. We highly recommend Helen to anyone looking for a reliable and caring pet sitter!
We couldn’t have asked for a better sitter for Diesel while we were out of town for two weeks! Sanaz was absolutely amazing with him. She didn’t just take wonderful care of him, she spent time training him, gave him so much love and attention, and kept us updated with tons of photos and videos, which gave us such peace of mind while we were away. Most importantly, we completely trusted her with Diesel and our home. She was reliable, caring, attentive, and clearly formed a real bond with him. In fact, I truly believe Diesel misses her! Since we’ve been home, he honestly seems a little heartbroken that his new best friend isn’t coming over anymore. That alone tells me how loved and well cared for he was while we were gone. I would absolutely recommend Sanaz to anyone looking for someone trustworthy who will treat their dog like her own. We will definitely be calling her again! ❤️
I have 2 small rescue dogs. They are nervous and timid. IULIA is so gentle and sweet with them. She communicates the whole time she is with them sending updates and photos. She is very detailed on what care each dog needs individually. We highly recommend them to anyone looking for a reliable, caring, and professional dog sitter. Thank you for taking such wonderful care of our furry family members!
Gillian was amazing!! She stayed at our house to watch our dog and two cats. She was very easy to communicate with and followed all directions! She kept us updated each day which was great. When we got home, the house was perfectly clean. I would highly recommend her!! She was also more than willing to do a meet and greet before the stay! Thanks Gillian!
Anthony did an amazing job caring for our dog and our home. Our dog is very shy but he took the time to build a great relationship with her. He even bathed her and left the house spotless! He provided is updates during our trip and really did an amazing job. We would love to have him watch her again in the future!
Caitlan was an absolutely wonderful dog sitter for our anxious dog, Alfie, and our cat, Roland. Caitlan made Alfie feel very calm and loved, and from the first moment they met I knew she'd be a great fit for an anxious doggo! Caitlan followed our requests to a T and went above and beyond with a checklist noting his meds being taken, and walks 2x a day. Alfie struggles with leash aggression with other dogs sometimes, and Caitlan really helped him with this behavior...he definitely seems to have improved! Roland, our cat, also struggles with wanting nighttime feeding and she managed to help him reduce his 'poking' for food behaviors down to just 1x a night. We didn't realize when we booked Caitlan that she is not just a dog/cat sitter but something of an animal therapist as well, lol! Caitlan communicated often about how they were doing, sent photos etc. We knew they were in such safe and loving hands with her! To top it all off, when we got back after three weeks she had washed her bed linens and sofa throw, and made us the most delicious banana bread. Caitlan was uber professional but most importantly she really connects with animals and intuitively seems to know what is best for them. We are definitely going to book her again for any future trips!
Brianna was amazing with our 10+ year old fur baby who has significant medication needs. She administered eye meds 3 times a day and gave him his night time allergy meds without fail. We came home to a very happy and healthy dog. Would highly recommend her services.
Bruna was absolutely amazing with my cat Carl and French Bulldog Daisy. I needed a sitter with less than 24 hours’ notice over the Fourth of July holiday, and she stepped in without hesitation. At the time, Daisy had just undergone surgery and required constant supervision along with medication administration. B handled everything flawlessly and gave me complete peace of mind while I was away. She sent frequent updates, photos, and messages, which meant so much given Daisy’s condition. Most importantly, it was obvious that both Carl and Daisy adored her. You can tell when someone genuinely loves animals, and they were comfortable, happy, and well cared for in her hands. I would not hesitate to book Bruna again and highly recommend her to anyone looking for a reliable, compassionate, and attentive pet sitter.
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