House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 143 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%.
“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!!”
“Molly is absolutely amazing. She is so patient and understanding with my reactive dog even when he's at his worst! Molly is a great communicator and I trust her with my dogs and home 100%!”
About: I have personal experience caring for both a dog and a cat, which has taught me how to provide loving, attentive care for pets with different personalities and needs. From daily walks and playtime to feeding, cuddles, and keeping pets comfortable, I understand how important it is to make every pet feel safe and loved. I’ll treat your furry family member like my own! 🐶🐱❤️ I’m looking for a part-time opportunity and am available a few days a week. I can fit pet care into my schedule and provide reliable, attentive care, making sure every pet feels safe, comfortable, and loved. I’m happy to coordinate with pet owners to find a schedule that works best for everyone! 🐾❤️ I provide loving and reliable care for dogs and cats in the comfort of their own homes. For dog walking, I focus on safe, enjoyable walks tailored to each dog’s needs, energy level, and pace. For in-home pet sitting, I make sure pets are fed, have fresh water, and receive plenty of attention, playtime, and affection. I also respect each pet’s routine and follow the owner’s instructions carefully to help their furry friends feel safe, happy, and comfortable while they’re away. 🐾❤️
“Third time having Lila house sit for our dog and cat and we love her! She is trustworthy, kind, and timely. Always sends pictures of our animals and is quick to respond. We will 100% keep booking with Lila as our regular pet sitter!”
“After several failed attempts of boarding my reactive dog, Mrs. Erika came to my rescue. I spent a week in Atlanta and Erika took amazing care of my pup Champ. She sent me pictures each day and made sure I felt comfortable and trustful of her. I have absolutely no complaints. She has been a life saver for me. She was patient, understanding, and flexible to my pups needs. I look forward to my next trip now that I no longer have anxiety about finding the perfect sitter. I recommend Mrs. Erika for anyone needing an in house sitter for their reactive dog. Also, my place was spotless when I arrived back home. 10/10!”
“Ariana is our favorite sitter for our cat, Remy. She’s very communicative and provides great updates while we’re away. Our place always looks better than we left it and our cat is always well-cared for when we return.”
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.
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: 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.
“If I could leave 10 stars I would. She house sat and cared for my 7 month old puppy and 14 year old senior dog so well. She went above and beyond especially because so many different things happened during the stay that were out of the ordinary (a prowler trespassing, a tree branch falling and damaging our fence, our puppy going into her first heat) and she handled it all with ease and grace. Will hire her again and highly recommend!”
“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.”
About: I have always been a dog owner my entire life, this is actually the first time where I do not have a dog, I am waiting for the right moment, but I would love to be around dogs and being able to be a huge help for all pet parents :) I work full time and am a student. Pet sitting would help so much in earning extra money. I love animals and would be happy to meet new ones. I will always make sure your pet is within my sight, I will ensure doors are not left open and when outside I will always ensure the safety of your fur baby.
About: I have grown up with pets of all sizes, including large dogs, cats, birds, rabbits, hermit crabs, and more. I give special attention to each pet's personality and needs to help give the best possible care. I'm currently working part time, so my flexible schedule allows me to work around your needs. I am typically available any day in afternoons and evenings, including weekends. I provide attentive, reliable care in your pet’s home, helping them stay comfortable in their familiar environment. I follow your pet’s routine closely, including feeding, exercise, playtime, medications (if needed), and lots of affection and companionship while you’re away.
About: In my household, we have always had a dog a part of our family. Growing up with dogs ignited my love for animals and being surrounded by pets. My most recent (now senior) dog has gone through surgeries, cancer treatments (with medication), and strict dieting so I am familiar with having to keep pets to a strict schedule and habits — while also giving them the best life possible with many walks and plenty of pets. I work a 9-5 job during the week with Fridays working remotely. I go in office usually from 9am -3pm and work the rest of the day remote but is subject to change. I am happy to accommodate and make it work for what you need and what works best for your pet(s)! I can also tomato by before and/or after work & dog/cat sit over weekdays and weekends. More can be discussed when booking, happy to answer any questions! I love and care for pets as if they are my own. In an initial visit meeting your animal(s), I take thorough notes to what your pet needs, what their usual schedule looks like, and any other important information regarding care. Making sure your pet is safe, healthy, and happy is first priority.
About: I’ve cared for dogs through sitting and boarding for friends and family, providing a safe, loving, and dependable environment while their owners are away. I make sure every dog is well taken care of by keeping them fed, active, and happy with daily walks, playtime, and lots of attention. I’ve also volunteered at animal shelters and fostered dogs in need, giving me experience with different breeds, personalities, and care needs. I treat every dog like they’re part of the family Pet care fits naturally into my daily routine because I currently work on building my at-home business, which gives me the flexibility and availability to dedicate quality time to dog walking, sitting, and boarding. I’m able to provide dogs with consistent attention throughout the day, including walks, feeding, playtime, bathroom breaks, and lots of care and companionship to ensure they feel comfortable and well looked after. I provide a safe, clean, and loving environment where pets feel comfortable, secure, and cared for at all times. In my home, I make sure pets have a calm space to relax, regular potty breaks, daily walks, playtime, fresh water, and feeding schedules that match their routine. I always pay close attention to each dog’s personality, energy level, and specific needs to help them feel at home. When caring for pets in a client’s home, I respect their routines and instructions to keep their pets comfortable and stress-free in their familiar environment. Whether it’s dog walking, drop-in visits, boarding, or overnight care, I prioritize safety, communication, cleanliness, and making sure every pet receives plenty of attention, affection, and proper care.
About: I have a passion for caring for all kinds of pets and have always had both a cat and a dog (and often more) in my life growing up. I'm experienced with dogs of all sizes. Your pet's needs and preferences will always be my top priority, and I will take any special requests or concerns seriously. For me, this isn’t just a job; it’s like a playdate with your pets! I’m a laid-back person with good intentions, so please feel free to reach out. Thank you, and I hope I can assist you. I currently work hybrid 2-3 days a week Thursday to Saturday from 10 AM to 3 PM, but I'm available most days of the week to care for your wonderful pets. I can take care of them in my home, yours, or simply take them out for walks. I will do my best to accommodate your needs, and I promise to keep your pets safe and protected at all times. Your pet's needs and preferences will always be my top priority, and I will take any special requests or concerns seriously. For me, this isn’t just a job; it’s like a playdate with your pets! I’m a laid-back person with good intentions, so please feel free to reach out. Thank you, and I hope I can assist you.
About: Caring for animals has been second nature to me since childhood. Over the years, my experience has spanned far beyond standard pet care- I've raised and cared for everything from dogs and cats to ferrets, bunnies, goats, pigs, and chickens. That diverse hands-on background taught me how to read animal body language, manage different temperaments, and handle daily routines with patience and confidence. Today, our home is a true animal-loving environment. We share our space with our sweet rescue dog, Valentina Bella, whom we welcomed into our family nearly two years ago. My two children have grown up sharing that same respect and gentle affection for animals, making our house a warm, nurturing second home. Expect to have a safe, calm environment: Your pet's comfort and routine come first. We prioritize safety, clear boundaries, and saree-free transitions. Attentive Care & Exercise: Whether your dog loves neighborhood walks, active playtime, or just lounging nearby while receiving gentle affection, their daily needs will be met. Consistent Communication: I know how important peace of mind is when you're away. You can count on regular updates, notes, and photos throughout their stay. Comfort with All Personalities: From outgoing social butterflies to rescues that need a little extra time and patience to feel secure, we know how to meet animals where they are. Because we already share our home with our own rescue dog, a steady, dependable pet routine is second nature to our household. My schedule allows for dedicated time before, during, and after work/school hours to give dogs the exercise and care they need. Mornings begin with breakfast and a solid walk to burn off energy before the day starts. During the day, our setup ensures pets are safe, comfortable, and never left unattended for extended periods. Evenings and weekends are completely centered around family and pets - featuring long neighborhood walks, play sessions, and calm downtime. We treat pet care as a priority and make sure visiting guests receive the exact same consistency, affection, and structure as our own dog. Safety is top priority. We start with a mandatory meet-and-greet to ensure compatible temperaments before any stay. Inside our pet-proofed, secure home, visiting pets are closely supervised, and slow, respectful introductions are always practiced. With years of experience managing diverse animals and rescues, I am vigilant about body language and routine boundaries. Your dog will never be left unattended with other pets or children without direct supervision. When walked, pets are always securely leashed. You'll receive prompt daily photos and honest updates so you always know your pet is secure and comfortable.
About: There has never been a moment where there has not been at least one dog in my home for the last 15 years. I have experience training both puppies and adult dogs. No dog is too much of a task and I look forward to working and walking your babies. I currently have a pretty free schedule and have plenty of time to work with your pups! Am also willing to adjust my schedule to better provide. I do not offer in home boarding at my home, but I absolutely love keeping your fur babies company in your home for as long as needed.
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
Bouvier was amazing with our dog. She sent picture updates, was very attentive, and left the house spotless. She even went above and beyond by washing the sheets and remaking the bed; and running a load of laundry we forgot about. This was our first time working with Bouvier, and we will definitely use her services again.
Helen was so amazing! I was super nervous leaving my boys alone for the first time and she was the best. They loved her and she kept me updated with pics and videos. She asks great questions and you can really tell she cares about their well being. She was respectful of our home during her stay. We couldn’t ask for a better and more trustworthy person.
It’s our first time looking for a dog sitter so I was very nervous about it but I’m so grateful for Lila! My anxious dog loved her and she did everything we asked for + more and updated us with pictures and what they did all day. She’s the best, highly recommend!!
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 !!!
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! ❤️
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
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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 is $94 per night as of November 2026. Most bookings cost between $42 and $278 per night. On Rover, 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 November 2026, there are 11,920 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 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 Meet & Greet.
sitters on Rover set their own cancellation policy, 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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