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%.
“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.”
“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.”
“Lexy house sitted for 3 nights. Kept the house really clean and the dog super happy! Received a couple updates and many pictures a day. Will definitely recommend her! Trustworthy and kind”
“So happy to have Lisa watching my 2 pups the last three days. It was our first time with her and won't be the last! I've already booked her again. Lisa was great about communicating with me. She sent an update and pics twice a day without my having to prompt her. She had great rapport with my dogs, even with shy Riley. The house was in great condition when I got home. Lisa really cares about animals and doing a good job. I appreciate all you did while I was gone.”
“Oh my gosh, she saved the day! We have a new puppy, but have some event we couldn’t get out of.. I needed an extra early morning request.., she said no problem, then I had to change it to an even earlier time, And she said no problem! She came on time.. sent pics.. couldn’t be more happier! Will definitely use her again!!”
“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!”
“Javi is terrific. He has taken care of my high energy dog multiple times. My dog took to him immediately! He loves dogs and they love him ! He is easy to communicate with and is super friendly.”
“Yana is so lovely! She talks to my dog, which he loves and gives him lots of cuddles. Very caring and clearly loves taking care of dogs, which makes all the difference. I feel comfortable with her taking care of my dog.”
“Jesse was wonderful! Communicative, punctual, and super sweet with my rescue dog Monty. Monty loves cuddles and affection and I got great picture updates of him looking super comfortable with Jesse. Would recommend!”
“We hired Arianna to watch our 2 kitties while we were on vacation and they immediately loved her. She sent a bunch of pictures and updates and was super communicative. We came home to a cute note, very happy kitties and a clean house. We will definitely be hiring her again when we go on our next vacation.”
“Taylor was a pleasure to work with! She was very communicative and kept us updated with our pet's needs. Letting us know if they were eating properly and how they were doing on their walks. Taylor was great with our dogs and sent wonderful pictures. She was very flexible when our dog had to have eyedrops given last minute right before we left. Her positive attitude and dedication gave us peace of mind while we were gone on vacation for a week. We knew our dogs were getting well cared for and wouldn't hesitate to use her again! We highly recommend her!”
“Erika was great with my Labrador, she took great care, kept me updated, and followed all the instructions. She is super nice! She also left the house super clean and a special note for us. I am sure we will use her again.”
“Alyssa did a great job watching our dogs at our house while we were away. You can tell they were well cared for and happy when we got home. She sent at least one update a day with pictures. Will definitely use her again in the future.”
“We had Austin housesit with our pet Ollie, for 5 days while we were on vacation. He was very sweet to our dog and provided the loving presence we desired for her in our absence. We will certainly hire him on our future vacations and will recommend him to our family members and friends.”
“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!”
“Jeremy is truly the best, he has watched our boys multiple times now and they can be a handful! Our pups are always in good spirits after hanging with him for a few days and our home is always very clean when we get back! He’s the best sitter we’ve had in the LA area 😊”
“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!”
“This was our first time having a stranger house sit for us and we were super nervous, but upon meeting Ellie we knew our pups were going to be in great hands! We were gone for about 3 days and Ellie sent us pictures and updates of the pups everyday. When we got back home we were so happy to see how well the pups and the house were taken care of. We are super happy with Ellie and will definitely be asking for her help in the future! Thank you Ellie!”
The median cost per night for house sitting in Winnetka is $65
Pet parents share their Rover experiences - Winnetka
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.
Yana stayed with my dog at my home for 5 days/4 nights. I am so happy I found her because she is so incredibly wonderful! She was accommodating to my odd traveling schedule, left my house better than she found it, and most importantly my (sometimes anxious) dog was calm and happy with her here. Yana is great at following instructions and she is also very proactive. I was able to relax on my trip because she sent me lovely updates of my dog and I could tell he was comfortable, happy, and very well cared for. I would wholeheartedly recommend 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! ❤️
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!
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.
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 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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