House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 121 pet parents in Winnetka have booked house sitting
Winnetka, Find top rated house sitting
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Jeni 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.”
“Iuliia was really great with our dogs Charlie and Pixie! She watched them for 3 nights at our home, and She sent us lots of pictures, videos, and updated us every day. We appreciate you watching them and caring for Charlie and Pixie! Thanks so much!”
“Bruna was absolutely amazing with my cat Carl and French Bulldog Daisy. I needed a sitter with less than 24 hours’ notice over the Fourth of July holiday, and she stepped in without hesitation. At the time, Daisy had just undergone surgery and required constant supervision along with medication administration. B handled everything flawlessly and gave me complete peace of mind while I was away. She sent frequent updates, photos, and messages, which meant so much given Daisy’s condition. Most importantly, it was obvious that both Carl and Daisy adored her. You can tell when someone genuinely loves animals, and they were comfortable, happy, and well cared for in her hands. I would not hesitate to book Bruna again and highly recommend her to anyone looking for a reliable, compassionate, and attentive pet sitter.”
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.
“Yana was amazing!! She watched our dog for 5 days in our home and did an amazing job caring for her. I think our dog may be sad to have us home and missing Yana! She sent lots of really cute pictures and videos too! We will be repeat customers for sure!!”
About: I have 3 dogs at home, two small and one large. I have had dogs all my life and I am comfortable with dogs of all breeds and sizes! I understand the importance of the first time meeting a dog and will be patient until they feel comfortable around me. I have worked with rescues before saving dogs from the streets which is where I learned a lot of my dog skills as well. I love my walks with my dogs and would love to walk yours! I do currently work full time but I am available after 5:00 PM Monday - Friday and all day on the weekends. I hope to get to meet your dog or dogs soon! I currently work full-time but am available for evening walks after 5 PM on Monday - Friday. On the weekends, I am available all day! I have experience dog sitting and always follow the instructions the owner has left for me. I am a guest in the home and always make sure I am on top of all my duties. I triple check everything is the way it should be prior to heading out the door to ensure the comfort and safety of my clients pet.
“Lilly was fantastic with our three dogs. Two of them are 15 y/o and needed a lot of personal attention - and she was terrific. The dogs all loved her, she stayed in touch with us and sent pictures. You know when you meet Lilly that you have a super dependable and kind person that will care for your pets like they were hers. The ratings only go up to '5' but she earned a '10'!!”
“We had a great experience with Geena. She took excellent care of both of our Labradors, Pilón and Clark. Clark is a young, energetic puppy with plenty of antics, and she handled him very well. It was clear that she knew how to work with dogs and how to manage his energy and enthusiasm appropriately. She also did a great job with Pilón, making sure both dogs were well looked after and had plenty of playtime and interaction. We felt confident leaving them in her care and appreciated her professionalism and experience. We would happily trust her with our dogs again and highly recommend her to anyone looking for a knowledgeable and reliable pet sitter.”
“Daniela was great with our puppy and our senior dog as well as multiple cats and birds when she house sat for us. We got lots of pictures and updates and could see the progress she was making in teaching the puppy to heel on walks. She went above and beyond to keep things organized and clean, which is not easy in our chaotic household. She even got our most timid cat to come out of hiding for treats. We’ll be booking Daniela for our next trip if at all possible.”
“Hailey is absolutely amazing! She takes the best care of my babies (big chocolate lab baby and sassy little cat) and they adore her! I feel no stress when I’m out of town knowing they are in good hands”
“Madelyn is now our 4-mo-old puppy's favorite person! She gave up her Thanksgiving to stay with Ziggy at our house, but it wasn't just a "stay." Madelyn played with her and give her so much love and attention. It was just what Ziggy needed and we were so happy to trust her with our puppy! We're also very happy that Madelyn will be coming back to stay with Ziggy again in a couple of weeks. Thank you, Madelyn!”
“We loved Caitlan and our little Mila was so happy. Thank you Caitlan. We came back from our trip and it was clear Mila was so comfortable and happy with your presence. We really appreciated the peace of mind that Mila was a loving hands.”
“Gillian takes great care of Pringle while I’m at work, and I really appreciate how punctual and responsive she is. I feel at ease knowing Pringle is in good hands, and I definitely plan to be a regular client!”
About: My family has owned dogs and cats my entire life. I don’t think there has been a single day in my life where I didn’t own a pet or have responsibility for one. Including the Marines under my charge. Animals. Seriously, though… Pets love me. I am also a firm believer in following instructions to a T. People are often surprised when I ask to meet their dog, they tell me that the dog is skittish or afraid, and then the dog walks slowly up to me like they’ve known me forever and then we’re best friends. I feed my two cats, Chief and Cosmos, daily at 8am and 8pm. Cosmos requires special dietary food, so my wife and I bought chip-specific feeders for each cat. I also make sure they stay physical with my fishing rod toys, as well as ensure clean facilities for the… you know. It all comes down to showing them love, providing for them, and protecting them. I treat my two cats like they were my own kids. We don’t deserve their love if we can’t give it to them. It’s inhumane.
“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.”
“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 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.
“My cat needs especial treatment due to his urinary issue. Leyla did a great job, feeding him on time with the exact instruction I asked her plus the medication. I recommend her to ALL cat's parents!”
The median cost per night for house sitting in Winnetka is $64
Pet parents share their Rover experiences - Winnetka
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!
Samantha was amazing! She kept in close touch with us, and our dog loved her! He was happy and relaxed when we got home. Samantha spent tons of time with him. I think he’s going to miss her, as are we. I highly recommend Samantha! You’ll feel so safe and secure when you leave your dog in her care.
Caitlan was an absolutely wonderful dog sitter for our anxious dog, Alfie, and our cat, Roland. Caitlan made Alfie feel very calm and loved, and from the first moment they met I knew she'd be a great fit for an anxious doggo! Caitlan followed our requests to a T and went above and beyond with a checklist noting his meds being taken, and walks 2x a day. Alfie struggles with leash aggression with other dogs sometimes, and Caitlan really helped him with this behavior...he definitely seems to have improved! Roland, our cat, also struggles with wanting nighttime feeding and she managed to help him reduce his 'poking' for food behaviors down to just 1x a night. We didn't realize when we booked Caitlan that she is not just a dog/cat sitter but something of an animal therapist as well, lol! Caitlan communicated often about how they were doing, sent photos etc. We knew they were in such safe and loving hands with her! To top it all off, when we got back after three weeks she had washed her bed linens and sofa throw, and made us the most delicious banana bread. Caitlan was uber professional but most importantly she really connects with animals and intuitively seems to know what is best for them. We are definitely going to book her again for any future trips!
Brianna was amazing with our 10+ year old fur baby who has significant medication needs. She administered eye meds 3 times a day and gave him his night time allergy meds without fail. We came home to a very happy and healthy dog. Would highly recommend her services.
We can’t recommend Melanie highly enough. Her communication was excellent throughout, and she kept us in the loop with regular photos and updates. It gave us real peace of mind knowing our dogs were in good hands, and we appreciated that she never left our pup alone for long stretches. We came home to happy, well cared for pup and will absolutely be booking with her again.
Bruna was absolutely amazing with my cat Carl and French Bulldog Daisy. I needed a sitter with less than 24 hours’ notice over the Fourth of July holiday, and she stepped in without hesitation. At the time, Daisy had just undergone surgery and required constant supervision along with medication administration. B handled everything flawlessly and gave me complete peace of mind while I was away. She sent frequent updates, photos, and messages, which meant so much given Daisy’s condition. Most importantly, it was obvious that both Carl and Daisy adored her. You can tell when someone genuinely loves animals, and they were comfortable, happy, and well cared for in her hands. I would not hesitate to book Bruna again and highly recommend her to anyone looking for a reliable, compassionate, and attentive pet sitter.
Yana is the best! She has helped take care of my dog many times and is consistently so amazing. She is very attentive to my dog’s well being and is a great problem solver too. She watches out to make sure my dog doesn’t eat random things during walks and thinks about the little things like the best time for his walk depending on how hot the pavement might be. When Yana is with my dog, I know he will be cared for so well!
We had a great experience with Geena. She took excellent care of both of our Labradors, Pilón and Clark. Clark is a young, energetic puppy with plenty of antics, and she handled him very well. It was clear that she knew how to work with dogs and how to manage his energy and enthusiasm appropriately. She also did a great job with Pilón, making sure both dogs were well looked after and had plenty of playtime and interaction. We felt confident leaving them in her care and appreciated her professionalism and experience. We would happily trust her with our dogs again and highly recommend her to anyone looking for a knowledgeable and reliable pet sitter.
I appreciated Emily’s observational skills and calm response to my dog being sick while I was gone. She took good care of her and used good common sense in caring for our dog. Our dog was happy and seemed fully recovered when we returned home. The house was clean and she went beyond to make sure everything was back to normal when we returned. Thank you.
Jesse was such a great help to me in taking care of my dog when I was setting up a party. My dog was a bit anxious and overstimulated from all my running around while doing party prep and Jesse helped calm him with cuddles and reassurance. It was a relief to not have to worry about my dog during my party because I knew he was in great hands.
Bouvier was above and beyond communicative and caring of our 2 senior Golden Retrievers, one with medical needs and the other that developed a medical need while we were gone. We felt in the loop the entire time although we were a Continent away. She took over sitting in between another sitter’s stay and was more than willing to communicate personally with her about the status of the pups. We are grateful to Bouvier and look forward to having her our pups in the future.
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 3 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 $94.35 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 12,034 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:
- 90% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 97% 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.
Connect anywhere with the Rover app
