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 was wonderful with our puppy, Bob. He had no accidents in the house, as he is in potty training. She played with him a lot, and he was a very happy puppy when we came home. She followed instructions and she was on time, and very nice. We will use her again! Thank you!”
“Jeni was wonderful. She's quick to respond - sends great pics, videos, and updates - and seems to know/understand dogs really well. We felt very comfortable with her staying at our home with our puppy.”
“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.”
“Went above and beyond to make sure that I felt comfortable, followed all directions and was very attentive and very flexible. Will definitely use her anytime. I’m in vegas thank you so much Cyndi .”
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.
“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!”
“We just did our first overnight stay with Daniela watching our two dogs and one cat. She was fabulous! We’ve never been comfortable leaving our dogs because they have some weird quirks — and one is quite reactive on walks — but she was a true pro and handled everything beautifully. We got lots of updates and photos and all the animals were very happy. She also went above and beyond to wash the sheets before leaving! We’ve definitely found our go-to sitter.”
“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.”
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.
“Leyla did an amazing job with my dog while I was out of town. She’s so caring and gave him so much love that I could see he was missing her. She updated me with pictures and videos every day plus all the activities and routine during the days. She followed all my instructions. I couldn’t ask for more. She left my place tidy and super clean. She became Pablito’s official dog sitter 🐶 Thank u Leyla for all your love and caring for him!”
“Taylor took great care of my two chihuahuas and home while my husband and me were gone for the holidays. We so appreciated her availability on Christmas! The dogs seemed happy when we returned and the house was in good order.”
“Nicola stayed at our house and watched our dogs for a week while we were on vacation. Nicola was fantastic with our dogs and took very good care of our home. Nicola was very communicative all week, sending great pictures of the dogs and the house. Nicola was a pleasure to work with, and we would definitely hire Nicola to help with our dogs in the future. We would highly recommend hiring Nicola for any dog/house sitting or dog walking jobs.”
About: I am a caring, attentive, and reliable pet caregiver with 10 years of professional experience. I have worked primarily with dogs, though I also have some experience with cats, small mammals, and birds. I treat every pet in my care as if they were my own, ensuring them lots of attention, affection, and love. I have experience working with dogs of many different sizes, breeds, and ages. I genuinely love and enjoy taking care of animals and hope you will choose me as your next pet caregiver! I am fortunate to have a very flexible part-time work schedule, which allows me to be available for all of your pet care needs! BOARDING: I live in a 2nd-floor apartment in a quiet, peaceful, and walkable community. I accept boardings for one family at a time, ensuring a calm and peaceful experience for all. Due to the quiet nature of my apartment community, I prefer to board calm-tempered dogs to avoid noise complaints from excessive and/or loud barking. I can board 2 dogs from the same family at a time, though for large dogs I limit to 1 due to the size of my apartment. I have a large and safe, pet-proofed balcony where the dogs are welcome to lounge and explore. I also welcome pets on my couch and bed to ensure maximum comfort. While boarding dogs, I make sure to be present all or majority of the time. HOUSE SITTING: For pet sitting in your home, I follow all instructions provided to me while staying respectful of your space and privacy. I always clean up after myself and leave the space cleaner than I found it.
About: Watching dogs for a living?! Who wouldn’t want that! I loved watching dogs for my family and friends for as long as I can remember, was and am happy to hear about Rover. Walk, wash, play, anything you need. I’m your pal! I’m currently working freelance so hours are all over, which allows me a heck of free time! I am able to work with your schedules and availability. I live in a gated complex, no running into the streets. The area is pretty spacious so walks may be down within the gated complex.
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 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.
“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 always enjoyed being around animals ever since I was a little kid. I have owned and cared for rabbits, dogs, fish, turtles and parakeets. I work full time as an educator so most of the year I am only available weekends. However I am currently available during weekdays due to spring break. I would be happy to care for your pet in my home or at your home if that is your preference. I have one dog at home which would be kept in a different area.
About: My name is Elena I have worked with animals since high school. I currently attend cal poly Pomona for animal science to go to vet school after. I currently work at an emergency and specialty hospital for pets in studio city. Well rounded in animal behavior and dos and donts. I have worked in the field for about 5 years from general practice to volunteer work to now. I have one client who always brings her pets for me to pet sit when she’s on vacation and I decided to pick up rover as a side gig since I can’t do a lot of hours at work due to school. I Love working with animals whenever I am not at the vet practice I help others on vacation or with busy schedules aid in animal care! I have a fenced patio/yard space! And i have a cat that is indoor full time, she grew up around dogs so is okay with interaction however if i step out to the house both dog and cat have separate rooms.
“Lexy did a great job with Kobe. Kobe is a high energy puppy , especially when meeting someone new and Lexy was patient with kobe and he eventually calmed down as Kobe got comfortable with Lexy and had a great overall experience. Highly recommend Lexy for her patience with dogs, attention to house instructions and competence.”
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
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.
Yana was an amazing dog sitter. She was extremely loving and kind to our two dogs. 💕 She followed our instructions and kept our house clean. Her communication was great; she sent a couple updates each day with photos and videos. We could tell our dogs were having a great time with her because they were extra playful. We highly recommend booking 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! ❤️
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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