House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 141 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%.
“IULIIA watched our dog again overnight for a second time and did great. We really trust her and know she is taking good care of our dog. We have already booked her again for another future trip!”
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.
“It is never easy leaving your pets when you have to go out of town, but Lila made it so much easier. She checked in with us often, sending cute pictures and videos. She was incredibly respectful of our home. Our animals loved being with Lila and we can’t wait to book with her again!”
About: What sets me apart is the genuine love and patience I have for every dog I care for. I treat every pup like my own, while making sure they feel safe, comfortable and loved. I’m attentive to their individual personalities, routines, and needs, whether they’re playful puppies, energetic adults, or sweet seniors. I’m also happy to provide plenty of walks, playtime, cuddles, and basic reinforcement of good behaviors. My goal is for both you and your pup to feel completely comfortable and confident while you’re away. I’m around animals for most of my days, so caring for pets is a natural part of my routine. My schedule is fairly open and flexible depending on the day, which allows me to accommodate different pets’ needs, routines, and care schedules. I’m happy to work with you to find a schedule that works best for you and your pet. I make sure every pet gets the care and attention they need, including regular walks, meals on their normal schedule, playtime, and plenty of love. I make sure they get their energy out and feel comfortable and happy while in my care. I also follow each pet’s individual routine and any specific instructions you provide.
About: I've fed, cleaned after, bathed, played with, and loved a lot of dogs as well as horses, cats, and fish. It's a privilege to help. I'm a creative freelancer working on several projects, so I set my own schedule and am very flexible! I usually fit my other responsibilities around being available for pet care at a moment's notice, whether it's a walk during some down time or dedicating the time to doing a sitting. I always make sure pets are safe, comfortable, happy, and feel loved and taken care of. I also value respecting your home and your privacy.
About: I have experience in caring for pets but also professional experience in the Veterinary field. I am a Vet technician so I am quite experienced with all pets and their needs. I currently work part time. My mornings are completely open and weekends as well! Please don’t hesitate to reach out to see if we can be a good fit! As an experienced pet owner/ vet technician, I understand every pet is different and depending on their personality I will work around each pets needs and respect owners requests.
About: I’ve been walking dogs and house sitting for years and have always grown up with pets of my own. I’m comfortable caring for dogs with different personalities, energy levels, and routines, and I genuinely love spending time with animals. I’m reliable, attentive, and will treat your pets and home with the same care I would my own! I’m currently working full time at a school, so I’m free during the week after 3pm and I’m free on the weekends for pet care or walks! I provide personalized care for pets in the comfort of their own home, helping them maintain their normal routine and reducing stress. Services can include feeding, providing fresh water, administering medications as directed, walking dogs, cleaning litter boxes or cages, playtime, exercise, and lots of attention and affection.
“Farrah was really great! She stayed at our house for a week with our dog and did an amazing job. She sent lots of updates and was always very reachable whenever we checked in, which gave us so much peace of mind. She was also kind enough to come by a few days before we left to do a walk-through of the house and meet our dog, which we really appreciated. We came home to a happy dog and a house left in great condition. We truly appreciated having someone so trustworthy and reliable caring for both our home and our dog. We would absolutely recommend Farrah and would love to work with her again.”
“Melanie was wonderful. She sent frequent updates, which made me feel so calm about my fur babes being with her. She was very flexible, kind, and caring. Would highly recommend!”
About: I have taken care of many dogs. I used to have a Samoyed and a multipoo myself for many years previously. I love how affectionate dogs are. I am great at sticking to feeding schedules. I enjoy petting and playing with a dog kindly and gently. I have a big backyard that is fenced where a dog can run and play safely. I work part time, not everyday, and just a few hours a day, so I am a great companion to your sweet lovable pet. I am gentle, caring, loving, warm hearted. I am very empathetic to pets because they are loving beings. I will often take them for bathroom breaks, pet, and feed on schedule. I want the pet to feel safe and happy and the owner to relax and enjoy their time away. I have a fenced backyard. I accept cats or small dogs only. The pet will have space to run and play. I am gentle with my voice and my affection to the pet. I have a big heart and am also good at keeping a feeding schedule. I am warm hearted and responsible.
About: Ever since I was little I’ve always had an unbelievable love for animals. I have been caring for pets since I was 12 years old, watching family, friends and neighbors dogs. I have also been working as a Veterinary Assistant/tech since 2021 and have my degree in Veterinary Technology. Caring for animals has always been my true love in life. I treat every pet as if they are my own, ensuring they receive love, attention, and the care they deserve, including never ending belly rubs. I’m committed to providing a safe and enjoyable experience not only your pets but you as an owner as well. Whether it’s an energetic pup or a senior pet who needs a bit more patience my goal remains the same. Need a cat sitter? I would love to watch your fur baby, do drop in visits or whatever else you may need. I understand the boundaries cats may have with touch and new people. I would love to meet you and your pet! I am currently working at an animal hospital in Encino and typically work Sunday-Wednesday 8am-7pm. Depending on the distance, I will be able to check in your pet during my lunch break at work. I am pretty flexible on Thursday, Friday and Saturday. I want not only your fur baby to be comfortable and feel safe but I want you as a pet owner to feel the same. I will treat your home with the utmost respect.
About: Dedicated pet professional with 6 years of experience. Highly skilled in safe medication administration, advanced canine care, and handling dogs of all sizes and breeds. Expert knowledge of brachycephalic health needs, backed by a decade of personal ownership of a Pug. Reliable, attentive, and trusted through years of diverse pet-sitting and walking experience. Working remotely from a fenced house allows me to balance professional focus with a peaceful home environment, enjoying the private outdoor space throughout the workday. Living in a fenced house has made me deeply vigilant. I always double-check gates, secure latches immediately, and watch for sliding doors to ensure zero escape risks.
“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!”
“Yoo Jee was so great with my dog Curly! She was very responsible and communicative, sent frequent updates, and gave Curly lots of pets and cuddles while I was away.”
About: Hi🐾 my name is Beray, i am 22 years old veterinary technician and a 1st year veterinary medicine student! In my free time i like to read (or study), watch movies, swim and cuddle with dogs❤️ I was taking care of dogs and cats just as a hobby only for people i knew, but decided i can help more pet owners and make their furry babies happy!! I have experiences with puppies and senior care. You will be receiving really nice photos of your pups🐶 I am at home 24/7 if needed (feel free to ask I don’t even leave for 5 minutes) no problem with that, home is fun with a furry baby we can play fetch, cuddle, watch movies!!! I know that all doggies need different care. For puppies, i am very good at potty training and obedience training. I also have first aid training🤍 Please read the following before booking either of these services: Day Care means: Between 0-10 hours Boarding means: Between 10-24 hours All of the pets i take care, they are my babies too!! They are all welcome for hugs and most importantly LOVE! For summer period i am free every day and i can start working really early if my client needs. I don’t like to go for walks so late for me and my client’s safety. We have a nice fenced backyard; we mostly play there and hangout i don’t let them out unsupervised. I only walk with leash, sometimes dogs see rabbits or squirrels and chase after them. We don’t want anyone to get hurt or scared 🫶🏻
“Antonia deserves 10 stars! She is lovely,kind, competent, and clearly loves animals. This was my first time having a petsitter in my home to watch my two little dogs and I must say I was a bit nervous. But Antonia washed away all of my doubts. For those of you who will be first-time petsitter users (and future users as well) Antonia is the way to go. Shes really a gift. Took excellent care of my pups and fed and walked them exactly as directed, gave them treats. She let them sleep in the bed with her. My pups fell in love with her. And she left my home immaculate! Also - she sent frequent videos of the pups so I could see how they were doing. I highly recommend Antonia to sit for your pets. They will be in great hands. I’m looking forward to working with her again in the near future. So glad I found her. Thank you, Antonia!!!”
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.
About: I've taken care of dogs of every kind since I was 12. Neighbors, friends and family have relied on me to walk, feed and bathe their pets. Animal lover will care for your pet with love, cuddles, and attention. Hello I’m currently working part-time, so I'll have plenty of time to play with your pups! I'm available for boarding on weekends, and weekdays and Holidays. Hello I have a fenced yard with grass and two friendly dogs to keep your fur baby company. I can easily crate your dog if needed...
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
Yana stayed at our home and took wonderful care of our Charlie girl during our six-day trip! She sent photo and video updates that gave us so much peace of mind. When the power went out at our house, she handled everything with ease, taking Charlie to her home and even moving all of Charlie’s frozen food to her own freezer so it wouldn’t spoil. We were so grateful for her thoughtfulness and flexibility! Her husband was also very kind and helped when we picked Charlie up. Yana truly went above and beyond, and we would happily book with her again!
Sam was amazing! Her communication is quick and clear. She is warm, friendly and smart. We left her with our year old dog (who can be quite high maintenance, and our senior cat while we were out of town, and Sam gave frequent updates and photos. If she had questions, they were always of a nature that let me know she was mature, and taking good care of our pets as well as our house. Everything was clean when we returned and our pets were happy! Highly recommend Sam🙏
Taylor was the absolute best! Our boy can be anxious and reactive and Taylor handled his reactivity like a champ and was such a calm presence for him. He cuddled up to her very quickly and it’s obvious he trusts her.. such a relief for us to know ghus is being well taken care of
Julia spent a full week with my two small dogs while I traveled. She was incredible. They are timid rescues. She won them over! She is so patient and gentle. She took the best care of them, walked them, and communicated with me all week long. She sent videos and photos daily. My dogs adore her and so do I
Emma was wonderful with Cosmo! She truly spoiled him and followed all of my instructions carefully. Since Cosmo is a senior, I really appreciated how gentle and patient she was with him, especially helping him up and down his ramp and taking him out in his stroller as instructed. She gave him lots of belly rubs, attention, and love, and it showed! When we got home, Cosmo was happy, relaxed, and showed no signs of stress, which gave me so much peace of mind. Emma also kept our house clean and sent daily updates with photos and videos, so we always knew how Cosmo was doing while we were away. I highly recommend Emma and will definitely be booking with her again. Thank you for taking such great care of our little guy! ❤️
Alice was absolutely incredible and took amazing care of Rocky! She was incredibly communicative and flexible, and left my home absolutely spotless. She sent tons of photo updates and loved Rocky as if he’s her own! I cannot recommend her enough and will definitely be booking with her again in the future!
It's always great when Anthony is available to watch our dog at our place. He is very calm and works great with her, even though she's quite shy. He always takes great care of our dog and our home. She's always happy when we come home and the house is always clean. Anthony always keeps in contact and provides updates. I would love to book him again.
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! ❤️
Shannon was wonderful! She provided thoughtful updates and loads of photos to make us feel at ease while we were away from our fur babies! She was flexible, responsive and gave our pups loads of love and snuggles! I will absolutely book her again when we need in home care!!
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!
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 house sitting
1. Search
Browse profiles of sitters near you who offer house 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 house sitting - Winnetka
Select a filter and find qualifying sitters offering house sitting.Sitters in Winnetka average 3 repeat house sitting clients
FAQs for House Sitting - Winnetka
Frequently asked questions about Rover
The average cost of House Sitting in Winnetka on Rover is $94 per night as of October 2026. Most bookings cost between $42 and $150 per night. 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 11,892 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.
<b>Tip:</b> 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 , 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 .
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 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 .
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.
Yes, you can find sitters who have experience with handling special pet needs in Winnetka. On Rover:
- 88% of sitters can help with special care needs
- 92% can help with giving oral medications or injections
- 96% 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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