House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 33 pet parents in Winnetka have booked house sitting
Winnetka, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Andrew did a great job with our two animals while we were on vacation for about a week. He’s taken great care while house sitting, got our mail, and cleaned our cats litter box. We can always count on and trust Andrew with our pets!”
“Samantha was recommended to me by her roommate, my dog's regular sitter. She was booked and referred me to Samantha. Samantha is a true professional. Not only she gave me updates and my geriatric dog, Rico Suave, the royal treatment. She also gave me peace of mind. I came back to a very happy dog that I don't think really knew I was gone due to all the special care he received. I will definitely book with her again if my regular sitter is not available.”
“Great experience with Alex! Communicative and flexible when booking, thoughtful and accommodating to my pup’s needs, and her warm and caring spirit quickly put both my anxious dog and I at ease ☺️”
“Shailyn is super patient and super skilled at reading pets! We are so grateful it has been Shailyn who has answered our requests to care for our loud, well-meaning and stubborn little guy in the wake of his sister’s passing. Shailyn is committed! ♥️😊”
“Keeley was an amazing sitter. Sent so many pictures and updates and truly just loved on our pet with cuddles, car rides and great walks and playtime. Left the house clean and tidy and was just a pleasure to work with. Will be rebooking her soon!”
“I was terrified about finding someone to watch my little Velcro baby. But Rebeca put me at ease. Her communication with me and love she gave my baby is beyond what I could have expected. I am so happy to have book with Rebeca and next time I am in Chicagoland I will definitely book with her again! Thank you Rebeca!!!”
“Iwona is great with our dogs! She has house sat for us twice and taken such amazing care of both the dogs and the house. She loves on our dogs so well, they barely even notice that we are gone!”
“Michael was fantastic! We have 2 large dogs, one has pretty bad anxiety, he handled him so well! He communicated, sent pictures, and really cared about taking care of our dogs! I would recommend him to anyone. He did some training with our dogs as well which helps with getting energy out, I just really appreciate how caring he was with our dogs!”
“Donna and Stephen knocked it out of the park again. We ran into flight issues for our travel and the team jumped into action. . .went above and beyond to make sure our Gypsie was well cared for in our absence. I will continue to have them care for our dog and highly recommend them for your pet.”
“Ella was great! She sent photos every day and took excellent care of our little fur baby and our home. We were able to relax knowing our pup was in good hands. We’ve already booked her for another in our home stay.”
About: I am currently a college student who loves animals. I have a dog and three cats at home, and I have volunteered at animal shelters in the past, so I’m very experienced with pets. While I am newer to house sitting, I am definitely not new to loving and caring for our furry friends! I work part time so I am available multiple times every day. I can stop by homes in the morning before work, and then after work in the afternoon and evening. I walk my dog and he loves our fenced in yard. I also am accustomed to feeding and cleaning litter boxes. And of course, care, love and attention are important every day!
“Tiffany was a fantastic house sitter for our 9-month-old puppy! She was responsive, professional, and made sure our dog felt comfortable and well cared for while we were away - which gave us great peace of mind. We will definitely use her again and highly recommend her!”
“Madeline was fantastic! Our dog was immediately smitten with her. Not only was Madeline attentive to all of the instructions I shared with her, but she was also flexible when it came to scheduling, since we didn’t know how long we’d be gone for. I’d highly recommend Madeline as a responsible, dependable, and caring sitter for your pets!”
About: Hi! I’ve been a lifelong animal lover, and I’ve had pets all my life — so I know how much pets mean to their families. My girlfriend introduced me to Rover, and since then, I’ve been all in. I currently walk up to 10 dogs a day and board around 2 dogs each month, and I truly enjoy every minute of it. Whether it’s a high-energy pup who needs long walks or a shy cat who just wants a quiet companion, I treat every pet like my own. I know how important trust is when it comes to pet care, and I always go the extra mile to make sure your furry friend feels safe, happy, and loved while you're away. I’d love the chance to meet your pet and give them the care and attention they deserve! Pet care is a major part of my daily routine. I work in real estate, which gives me a flexible schedule and plenty of control over my time. This flexibility allows me to dedicate consistent blocks of time each day to walking dogs, doing drop-in visits, and boarding pets comfortably in my home. Whether I’m caring for pets in my home or in a client’s home, safety and trust always come first. In my home, I create a calm, clean, and pet-friendly environment. I make sure there are no hazards within reach, keep any unfamiliar pets separated as needed, and provide plenty of space for relaxation, play, and personal time. I follow any routines or rules you provide so your pet feels comfortable and secure—just like they would at home. When I care for pets in a client’s home, I treat it with the same respect and care I would my own. I follow all instructions closely, keep your pet’s schedule consistent, and provide regular updates so you can feel confident they’re in good hands. I’m always attentive to their behavior, energy levels, and comfort to make sure they’re safe and happy throughout the visit. Whether it’s walks, playtime, meals, or quiet companionship, I’m committed to providing a trustworthy, low-stress experience for both you and your pet.
“Kevin was wonderful. We could not have been more confident in his ability to care for our pup during our trip. He asked all the right questions and truly paid attention to detail. During the stay, he sent plenty of updates and pictures which made us so happy to see! He was prompt, professional, and friendly! Our normally nervous pup warmed up to him almost immediately which just shows how lovely he is. Ollie loved him! He drew us a custom picture of Ollie and it truly is the coolest thing ever. We’ll be hanging it up! If you’re looking for a sitter who is attentive and will love on your animals the way you would, Kevin is your guy! Thank you Kevin for taking great care of Ollie!”
“Jiayi was AMAZING with our pets!! We have a ZOO and she was so on top of everything. She sent photos and reached out with any questions and made me feel very comfortable having my fur babies in her care. I would recommend her to anyone. She’s really a gem. Thank you Jiayi!!! We will definitely use you again.”
About: I believe in maintaining your pet's routine as closely as possible, minimizing stress and making their time without you feel seamless. I'm not just a sitter; I'm a dedicated, compassionate companion who genuinely loves animals and treats every pet as if they were my own. As a teacher, my summers are completely free, making it the perfect time to dedicate myself to pet care. I live only a half block from a large park and am very close to the lake, which is ideal for long walks. I genuinely love walking, so integrating multiple walks throughout the day for your dog is a pleasure, not a chore. This prime location also offers easy access to plenty of green space for playtime and exercise. Services include feeding, fresh water, walks, playtime, litter box/cage cleaning, medication administration, and plenty of cuddles. I'll also bring in your mail and water plants, giving you complete peace of mind while you're away.
About: I've been a dog daycare attendant for 6 years and have been involved with dog sitting for the same period, caring for a range of dogs of various ages! Have suitcase, will travel! When not working at K-9 Luxury Pet Hotel Sun-Thurs, 6-2, I'm available to come and stay with your pup, including weekends and holidays, to offer quality care. I offer round the clock monitoring and feeding schedules, any medication administration while also watering plants, monitoring mail and packages and ensuring property is secured.
The median cost per night for house sitting in Winnetka is $50
Pet parents share their Rover experiences - Winnetka
Rebeca did a great job house sitting for us while we were out of town! Our dog is normally slow to warm up to people but she really opened up to Rebeca very quickly. She obviously cares a lot about pets, was proactive about confirming appointments and did a great job communicating with us and giving updates during her stay. We look forward to having Rebeca watch Izzy again in the future. Thanks!
Shailyn watched my dog for a few nights, and I have nothing but good things to share! Shailyn is responsive in booking the service and scheduling a meet and greet. She shared plenty of pictures and updates throughout the weekend, and definitely made me feel more comfortable about being away from my pet!
Madeline was fantastic! Our dog was immediately smitten with her. Not only was Madeline attentive to all of the instructions I shared with her, but she was also flexible when it came to scheduling, since we didn’t know how long we’d be gone for. I’d highly recommend Madeline as a responsible, dependable, and caring sitter for your pets!
Ella and her partner were terrific! I had to board my three month old puppy and was nervous about leaving her with someone so soon but the daily updates and pictures assuaged my fears! They were kind, patient and even gave me some training advice. I wouldn’t hesitate to use them again in the future. Georgie had a blast!
Rosy and Josh were excellent house sitters. They were great communicators with frequent updates on how Izzy was doing. They definitely gave her lots of love and attention while we were out of town. We could tell when we got back home that she was very comfortable with them and had a good time. We will definitely be asking them to house sit again for us. Thanks!
Jiayi was AMAZING with our pets!! We have a ZOO and she was so on top of everything. She sent photos and reached out with any questions and made me feel very comfortable having my fur babies in her care. I would recommend her to anyone. She’s really a gem. Thank you Jiayi!!! We will definitely use you again.
We cannot say enough good things about Ana! We hired her to house sit and pet sit during our vacation, and we were very nervous about leaving our five-month-old puppy for the first time. From day one, she made everything feel easy and completely worry-free. She kept us updated every morning and evening, sent lots of pictures, and clearly gave our puppy so much care and attention — plenty of walks, cuddles, and patient, expert handling of teething/nipping. It was also such a relief to have someone we trusted at the house to bring in packages and mail and let our cleaning crew in. We came home to a happy puppy and a house that was in the exact condition we left it (maybe even a bit cleaner!). Overall, an excellent experience — we’d hire her again in a heartbeat and recommend her highly.
Katelyn was timely and wonderful for popping in and taking care of the cats. She communicated well and dealt with any request we asked. We’re extremely grateful for her being prompt on a short notice. She followed instructions extremely well. We appreciate her effort.
As the owner of 3 dogs, Andrew is very knowledgeable about dogs. He immediately connected with our dog right when he walked in the door. Andrew took her outside and to the basement to get exercise and have some play time. He did a great job! I’d recommend him to any dog-owner for pet sitting.
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.
Meet local sitters who will treat your pets like family
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 near you
Select a filter and find qualifying Winnetka sitters!Sitters in Winnetka average 4 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 $66.6 per night (as of July 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 July 2026, there are 7,889 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:
- 93% of sitters can help with special care needs
- 94% 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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