House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.

Over 132 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.”

“Jen helped us with our pups at our house overnight and with a last minute drop in visit while we were out of town. She is reliable, responsible, and quick to respond! Thank you so much!”

“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.”

“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.”

“Lila was great! She was very communicative and provided regular updates. We returned to a clean house and happy dogs. We will definitely rebook with her in the future.”

“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! ❤️”

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.
“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!!”

“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!”

“AMAZING!!! I just got a new pup only 9 weeks old and we have been attached at the hip. I had to go to an office lunch and was in such a stress to find him someone good. After being cancelled on I found Daniela. I knew off the bat she was a dog lover because she didn’t mind my little Harlows kisses ! She was truly great and I felt so relieved. She sent tons of feedback and pictures and even waited for me as I was running late. 100%%% recommendable. Thank you daniela!”

“Taylor was really patient with Luna, and built a relationship with her overtime. We are so grateful to have found Taylor and recommend her to others. She is a welcome addition to the pack! 🐾”

“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!”
“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: I’m a reliable, attentive, and caring dog walker and sitter who treats every pet like my own. I prioritize safety, consistency, and making sure dogs feel comfortable, happy, and well-exercised. I’m great with different temperaments, follow instructions closely, and communicate clearly with owners. Whether it’s a quick walk or an overnight stay, I make sure pets are well cared for and owners feel fully at ease. I work in the restaurant business waiting tables at night. So I’m free during the day whenever someone needs me to walk their dog or come over to let them out. Always on time. Or even a little bit early. Very patient willing to walk dogs and let them out when needed. Non aggressive with the pets

About: What sets me apart is the genuine love and patience I have for every dog I care for. I treat every pup like my own, while making sure they feel safe, comfortable and loved. I’m attentive to their individual personalities, routines, and needs, whether they’re playful puppies, energetic adults, or sweet seniors. I’m also happy to provide plenty of walks, playtime, cuddles, and basic reinforcement of good behaviors. My goal is for both you and your pup to feel completely comfortable and confident while you’re away. I’m around animals for most of my days, so caring for pets is a natural part of my routine. My schedule is fairly open and flexible depending on the day, which allows me to accommodate different pets’ needs, routines, and care schedules. I’m happy to work with you to find a schedule that works best for you and your pet. I make sure every pet gets the care and attention they need, including regular walks, meals on their normal schedule, playtime, and plenty of love. I make sure they get their energy out and feel comfortable and happy while in my care. I also follow each pet’s individual routine and any specific instructions you provide.
“Molly watched our two cattle dogs for a weekend away and we were so relieved to have someone who loves dogs so much and has so much experience. Our dogs warmed to her right away and we felt confident with them in her care.”

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.

“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!”

About: Hello, my name is Emily Woodland. I have 2 documented experience at dog board facility in Calabasas. I also have done 3 house sits while the family was away. I can do dog walking as well as feeding and play time. I own 2 dogs and 3 cats I know how to clean a litter box, feed dogs and cats, walk dogs, and play. I feed my dogs and cats early in the morning and in the evening. If I am off of work late my dog insists on going for a walk and I end up walking him at 11:30pm sometimes. I clean my cats litter box everyday before work. I usually enjoy going to clients homes more. I feel as if the dog may have less stress instead of being left with a stranger in a different home. I like giving the dogs treats to help them gain their trust. I can do walks, feedings, play time. Whatever you need.
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
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.

We had a great experience with Samantha! She was very thorough with our instructions and sent pics and updates during the stay. She was also forthright with us about getting sick before our booking started so we could make an informed decision about whether or not we still wanted to proceed, which we thought was a responsible and classy move.

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! ❤️

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!

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!

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 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 September 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 September 2026, there are 11,934 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.







