House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 130 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 is a talented, trusted, handler. She is kind, patient, punctual, honest, friendly, fun, and extremely loving. I can’t possibly express how grateful I am to have Jeni help me with my precious dogs. Her expertise, patience and knowledge have added so much to their lives. They both enjoy-walks, playtime, socialization. My dogs, Brutus (6 year old male Pekingese) and Rambo (1 year old male pug mix, rescue, are thrilled when Jeni comes to take them for their walks, and play dates. Rambo is very shy and panicky. Jeni takes as much time as needed to let Rambo settle which is within seconds. Brutus loves everybody so he and Rambo enjoy their time with Jeni tremendously. Highly, highly, recommend Jeni. I welcome any questions.”
“IULIIA watched our dog again overnight for a second time and did great. We really trust her and know she is taking good care of our dog. We have already booked her again for another future trip!”
“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'!!”
“Molly was incredibly flexible & willing to work with us to make sure our 7 month old puppy was adequately cared for while we were in and out over the long weekend. She was attentive to our pup’s needs, and provided care as if our pup was one of her own!”
“Sanaz took care of our two dogs with so much care while staying at our house. She also watched over our bearded dragon and three leopard geckos, making sure their lights were on and off when they were supposed to be and their water topped up. I would have her in our home again! I felt very safe with her care and attention to all. Thank you, Sanaz!”
“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.”
“Larry was an excellent dog sitter for our pup. Our dog is a COVID dog and used to being with someone 24/7. Larry stayed at our house and walked, played and kept our pup company. He was able to bond with Mozzi the first day. We came home to a clean house and a very happy dog. We would definitely hire Larry again. So glad we found him on rover.com.”
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.
About: I have about 7 years of pet handling experience from my own animals to volunteering at animal shelters in LA. I have worked with dogs and cats of all ages, from puppies to seniors. I have gained experience from my own dogs, one of which was blind and deaf. With over 250 hours volunteering at my local city animal shelter, I gained additional experience caring for cats, dogs, rabbits, hamsters, and guinea pigs. I cannot wait to meet your furry friend! I currently have a very flexible schedule. I am usually busy on the weekends, but I could make myself free if I am given enough notice. When caring for a client’s pet, safety is very important to me. Following the owner’s rules and ensuring your pet is cared for and loved while you are away is my number one priority :)
About: Animals have always been a huge part of my life, and I treat every pet like they’re my own. I have experience caring for dogs of all ages, from energetic puppies to senior dogs who need extra patience, medication, and specialized care. I’m dependable, attentive to each pet’s routine, and committed to keeping them safe, happy, and comfortable while you’re away. Whether it’s walks, playtime, feeding, or simply providing companionship, I’ll make sure your pet receives plenty of love and attention. My schedule allows me flexibility for walks, drop-in visits, and pet sitting throughout the week and on weekends. I pride myself on being reliable, punctual, and responsive, and I always make sure pets stay on their normal routine. Your pet’s safety and happiness are always my top priorities. I understand how important it is to trust someone with a beloved family member, and I take that responsibility seriously. I carefully follow each owner’s instructions regarding feeding, medications, exercise, and routines while providing plenty of love, attention, and supervision. I strive to create a calm, positive environment where pets feel comfortable and secure, and I’ll keep you updated with messages and photos/videos; as many as you need so you can have peace of mind while you’re away.
“Ariana stayed at my house to watch my two dogs and was tremendous. She’s trustworthy, good communicator, loves animals, and responsible. I’d give 6 stars if I could and look forward to using her again!”
“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!!”
“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.”
“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 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: I am a veterinary technician who has worked in the veterinary field for 5+ years. I love all animals and have experience handling/caring for dogs, cats, rabbits, birds, pocket pets, and a variety of reptiles. I am a UC Davis Alumna and have a bachelor's degree in Animal Science. I am currently a CVM student at MWU. With my extensive knowledge of animal behavior and handling, I am well-prepared to care for pets of all species. I am comfortable with medication administration, including giving pills, liquid medicine, and insulin shots. Put your mind at ease with a pet sitter who truly cares for your furry, feathery, and scaley friends. If you have any questions please don't hesitate to reach out! :) I have a very flexible schedule. I am also available to stay overnight at your house to keep your pets company, let the gardeners in, take the trash out, make sure your plants are watered, mail is taken in, etc. Dog walking: Your pets' safety is always my top priority. I only walk pets from one household at a time to ensure they have my undivided attention. I will keep an eye for any signs of heat distress during the summer and ensure the pavement is an appropriate temperature for walks. If deemed unsafe, I will contact you immediately to discuss postponing the walk at a later time. House sitting: I am very reliable and take pride in ensuring your pet is in the safest hands while in my care. I am also very accommodating with any special requests for your fur babies. Does your dog like to get pup cups from Starbucks? Do they have a favorite treat? Does your pet like to get brushed? Let me know so I can provide your beloved fur babies with the best care possible!
About: I’ve taken care of my family’s pets like dogs and cats while they’re gone and follow their instructions on when to walk, feed, and play with them. My schedule is currently free since I am a student and it is summer so I’m on break meaning I have time to tend for all of your animals needs! I have a big backyard where your pets can run around in to their hearts content. It is enclosed with a gate so they won’t be able to run out.
“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!”
“Daniela took great care of both our cats and our home. She was communicative, professional, and caring. I would definitely book her again and recommend her to anyone I know.”
“Kimberly was amazing!! I highly recommend her for your home and pet sitting needs. She is extremely communicative - always answers my messages right away and sends lots of photos and videos. Kimberly is flexible and easy to work with. She's friendly and my pets took a liking to her right away! I was very nervous about leaving my babies (2 dogs and 2 cats) with a stranger, but her work ethic and my happy animals made it much easier. Thank you, Kimberly! <3”
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
Jennifer was great, in the end, my dog was happy and stress free when i returned from a trip, quite a feat for a dog with separation anxiety. She befriended my dog to make it feel taken care of and loved, and it shows. My house was in the exact shape I left it as well. We could not be happier with Jennifer, we plan to use her services again!!
I have 2 small rescue dogs. They are nervous and timid. IULIA is so gentle and sweet with them. She communicates the whole time she is with them sending updates and photos. She is very detailed on what care each dog needs individually. We highly recommend them to anyone looking for a reliable, caring, and professional dog sitter. Thank you for taking such wonderful care of our furry family members!
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!
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.
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
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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 for House Sitting in Winnetka on Rover is $94.35 per night (as of August 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 August 2026, there are 11,825 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.
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