House Sitting Winnetka
Find a loving house sitter to watch over your pets and your home.
Over 33 pet parents in Winnetka have booked house sitting
Winnetka, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Alex was great our dog Lulu had a great time with her. She diligently said updates and responded very quickly to questions and shared lots of pictures! Our house was immaculate when we came home! We will always be using Alex from now on whenever possible! Your pets in great hands with her!”
“Andrew did a great job with my pooches. I think they didn’t even miss me after three days being gone. He was very quick to respond and was great with the communication. The dogs instantly took to him when they met him. Would definitely use his services again.”
“Jason was so awesome with our young golden retriever. Took tons of great photos and kept her happy all weekend. Super communicative and the house was in perfect shape on our return. I will def book him again if given the chance!”
“Alyssa was great! She was super flexible with our schedule, she showed up in a timely manner, and she really cared for Lucy. She played with her, gave her treats, let her outside and have her lots of company! She was great and we are definitely rebooking!”
“Donna and Steven were great. We adopted our very first dog this year and was not sure how Alduin would be while we went away for the weekend. Donna and Steven gave us as much time as needed for Alduin to get used to them. Teemo, his cousin was also visiting from Los Angeles and Donna and Steven also took time to come out and meet both of them when Teemo arrived. We left them to Donna's care the whole day Saturday and Sunday and Saturday evening. Everyone got along well, the puppies were well taken care of. In addition to Alduin and Teemo, they also took care of our 2 fish tanks, and Lisky our gecko lizard. I would ask Donna and Steven again to watch our beloved pets and recommend to anyone who needs pet sitting services.”
About: My names Gail! I am 26 years old and look to make some new furry friends. I have experience watching dogs and cats! I have gone to the clients house to watch the dog/cat or I pop in to make sure they are fed, go to the bathroom, and make sure they are walked and played with so they don’t feel lonely. I have also house sat as well if needed! I have my own way of transportation and super flexible in times. I like to take pictures to send to the families of the pet. I love being around dogs and cats! I currently work about 5-6 days a week. I do choose my own schedule at the end of the week, so I am very flexible on time! I have my own car, so I am able to get around very easy. I am able to put puppers in or out of crates if needed! I am able to distribute any medications to pets. Making sure the pets feel safe and comfortable while their family is out of town!
“I was terrified about finding someone to watch my little Velcro baby. But Rebeca put me at ease. Her communication with me and love she gave my baby is beyond what I could have expected. I am so happy to have book with Rebeca and next time I am in Chicagoland I will definitely book with her again! Thank you Rebeca!!!”
“Addison was awesome from the very first message, where she initiated the meet and greet. She was great, very communicative, professional, and Tessa, our dog who has high anxiety, seemed to really like her when they first met. When we got home Tessa was super happy so we couldn't be happier with Addison. We would definitely use her again if we had the opportunity to.”
“Kevin was wonderful. We could not have been more confident in his ability to care for our pup during our trip. He asked all the right questions and truly paid attention to detail. During the stay, he sent plenty of updates and pictures which made us so happy to see! He was prompt, professional, and friendly! Our normally nervous pup warmed up to him almost immediately which just shows how lovely he is. Ollie loved him! He drew us a custom picture of Ollie and it truly is the coolest thing ever. We’ll be hanging it up! If you’re looking for a sitter who is attentive and will love on your animals the way you would, Kevin is your guy! Thank you Kevin for taking great care of Ollie!”
“Darla is amazing! Our two dog love her and always have so much fun when she comes to stay. An added plus, is that she takes great pictures of our fur babies while she’s here.”
“Madeline was fantastic! Our dog was immediately smitten with her. Not only was Madeline attentive to all of the instructions I shared with her, but she was also flexible when it came to scheduling, since we didn’t know how long we’d be gone for. I’d highly recommend Madeline as a responsible, dependable, and caring sitter for your pets!”
About: I grew up with dogs, cats, and lizards. I have worked at an animal sanctuary, I have worked with disabled animals, and will give your pet the attention and love they deserve. I just graduated from the university of Vermont with a bachelor's degree in philosophy, I am taking a few months off of my regular 9 - 5 to take time for myself so I have a very open schedule. There is no time too early or too late for me to come help, just let me know what works best for you and your animal. I will feed, play with, walk, and spend time with your animal to make sure that they feel loved and cared for. I have no problem staying the night if your animal gets anxious without people around or making multiple visits within a single day.
“Valentyna was terrific with my anxious dog, comforting him during a thunderstorm. She was thorough in caring for our dog and asked questions when she needed clarification. We will definitely use Valentyna in the future.”
“Tiffany did a wonderful job taking care of my anxious dog Churro! My house was spotless when I got home and she sent regular photos and updates, and handled his medication schedule too. He was happy and well cared for all week. Churro and I look forward to working with Tiffany again!”
“Jiayi was AMAZING with our pets!! We have a ZOO and she was so on top of everything. She sent photos and reached out with any questions and made me feel very comfortable having my fur babies in her care. I would recommend her to anyone. She’s really a gem. Thank you Jiayi!!! We will definitely use you again.”
The median cost per night for house sitting in Winnetka is $50
Pet parents share their Rover experiences - Winnetka
Ella did a great job with our dogs. We have always boarded our dogs at kennels and this was the first time we had someone stay in our home with our dogs. We were very nervous about how our dogs would react, and more importantly how a dog sitter would handle our dogs. Ella seemed to genuinely care about our dogs and this gave us great peace of mind while we were gone. She would send us an update each morning with a couple of pictures. I really appreciated her quick responses to my text before we left on our trip. It never took her more than five minutes to respond to one of our texts. We wouldn't hesitate to use Ella again if she would be willing to stay with our dogs.
Melissa sent updates of the fun she had with my dogs, never hesitated to ask if she had a question, followed directions perfectly, and left my house cleaner than I left it!! I wanted a sitter who truly would spend time with my dogs as they are used to someone here mostly at home and Melissa did just that! She showed love and care for my dogs the week we were away. Thank you, Melissa!!
We had a great experience with Jiayi! She was incredibly communicative, respectful, and thoughtful throughout her stay. She kept us updated and was very easy to coordinate with. We really appreciated how responsive and responsible she was, and we’d be happy to have her sit for us again!
Addison was awesome from the very first message, where she initiated the meet and greet. She was great, very communicative, professional, and Tessa, our dog who has high anxiety, seemed to really like her when they first met. When we got home Tessa was super happy so we couldn't be happier with Addison. We would definitely use her again if we had the opportunity to.
Shailyn graciously agreed to come sit with our anxious dog on short notice which we greatly appreciated. She offered to come over early to have more time to meet with Zoey before our scheduled departure time. Shailyn has a wonderful calm and peaceful energy and it was clear that Zoey was happy in her company. We would absolutely have Shailyn back to care for our dog.
Madeline was fantastic! Our dog was immediately smitten with her. Not only was Madeline attentive to all of the instructions I shared with her, but she was also flexible when it came to scheduling, since we didn’t know how long we’d be gone for. I’d highly recommend Madeline as a responsible, dependable, and caring sitter for your pets!
We cannot say enough good things about Ana! We hired her to house sit and pet sit during our vacation, and we were very nervous about leaving our five-month-old puppy for the first time. From day one, she made everything feel easy and completely worry-free. She kept us updated every morning and evening, sent lots of pictures, and clearly gave our puppy so much care and attention — plenty of walks, cuddles, and patient, expert handling of teething/nipping. It was also such a relief to have someone we trusted at the house to bring in packages and mail and let our cleaning crew in. We came home to a happy puppy and a house that was in the exact condition we left it (maybe even a bit cleaner!). Overall, an excellent experience — we’d hire her again in a heartbeat and recommend her highly.
Katelyn was timely and wonderful for popping in and taking care of the cats. She communicated well and dealt with any request we asked. We’re extremely grateful for her being prompt on a short notice. She followed instructions extremely well. We appreciate her effort.
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 4 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 $66.6 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 7,755 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:
- 93% of sitters can help with special care needs
- 95% 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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