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.
“Andrew did a great job with our two animals while we were on vacation for about a week. He’s taken great care while house sitting, got our mail, and cleaned our cats litter box. We can always count on and trust Andrew with our pets!”
“Jason did a great job watching our dogs. He sent frequent, high quality photos throughout the stay, which we very much appreciated. He gave our pups lots of outside time and dealt well with administering their meds. We’d book with Jason again and recommend him to others.”
“Rebeca is an amazing dog walker! She was incredibly attentive and kept us updated throughout the entire time with plenty of pictures and videos, which we really appreciated. It gave us so much peace of mind knowing that Ripp was being so well cared for and was in such great hands. We could tell she genuinely cares about the dogs she works with. We wouldn’t hesitate to book with Rebeca again and highly recommend her to anyone looking for someone trustworthy and caring!”
“Sam was great with on our first experience having her watch our two dogs. The dogs were so happy when I returned, complete with background music playing to keep them company until I arrived home! Looking forward to having Sam back again soon!”
“Donna and Stephen stayed at our home to watch our older Samoyed. They were great communicators and took amazing care of our house. We would absolutely work with them again!”
“Gail is the best!! She took time to meet up with me beforehand to confirm all details and meet my kitty and she was very responsive, sweet and kind, and she gave my kitty a lot of love and company. My kitty is just as happy and active when I returned home. She is super responsible and even took care of my apartment for me.”
“Katelyn was great with our fur babies! She sent plenty of photo updates throughout the booking. She updated us about anything going on with the kids and asked questions along the way. We really appreciated her communication! The dogs loved her during meet and greet. I’m sure they wanted her to stay with all the doggy cuddle puddles! Would definitely book her again! It was so reassuring to have someone reliable, communicable, and compassionate. Made our vacation a breeze. We missed our doggos, but didn’t have to worry or stress with Katelyn!”
About: I'm attentive, detail-oriented, and generous with love and affection for all dogs I have the privilege to take care of. I have experience helping my family take care of our beloved dachshunds throughout my childhood (3 over the course of my life). I also have dog-sat for numerous families back when I lived in Minneapolis. I'm a dog lover through and through. I'm a busy grad student at Northwestern, so I can't have a dog of my own right now. Pet-sitting allows me to fulfill that desire for puppy cuddles when it fits my schedule! I have classes during the day and club activities at night, but lots of flexibility in my schedule to drive to pet sitting appointments. I would prefer to take care of dogs in their homes and go for walks in their neighborhood rather than stay in my small studio apartment. This makes the dog feel safe in their space. I am dedicated towards making dogs feel comfortable with me by following their existing routines and spending as much time as I can with them.
“Phenomenal experience while he house sat and dog sat for us. My dog loves him and he was so communicative and easy to work with! We unfortunately had a gas leak issue during our trip and he was not only quick in identifying it, but worked with our maintenance crew and updated us every step of the way. Would hire again easily!”
About: I grew up in a dog home and have always loved dogs. I worked at a daycare/boarding facility for 3 years, and finished my work there as a supervisor. There, i gained experience in caring for dogs from 3 months old to 18 years old, as well as dogs with health complications and mobility difficulties. I also volunteered at an animal shelter for 2 years as a handler for behaviorally challenged dogs. I currently work at another dog daycare boarding/training facility. I work Sunday and Friday afternoons, as well as Tuesday and Thursday mornings. I am available and looking forward to filling my time with more pups! Body language is a very important part of communication and safety with dogs. When i'm with dogs, i'm extra careful to pay attention to what they are telling me with their body! When im meeting a new dog, I make sure to avoid eye contact, turn sideways, and get lower to the ground, all things that show your pup im a friend, not a threat. All in all, every dog is different, has their own personality, likes, and dislikes. I make sure I learn and respect them so I can build trust, and keep everyone safe and happy.
“By far & away Coty was THE BEST dog sitter/house sitter I've ever had. She was incredibly responsive and communication cadence was exactly as I like. She sent me a daily update including pictures and video. She was extremely organized, asked all the right questions in preparation for the stay. The best part was coming home to my home cleaner than I left it. If I could give Coty 10 stars I would! Will definitely use again!”
About: No two dogs are the same, and I adjust my care to match. I have experience with puppies — including reinforcing basic commands and helping build good habits early on — as well as senior dogs, where I adjust to a slower pace and give extra attention to comfort and mobility. I pay close attention to each dog's personality and energy level, adapting my approach whether that means more playtime and structure for a young pup or a calmer, gentler visit for an older dog. I communicate clearly throughout every visit with updates and photos, and I always leave things clean and tidy behind me. Available for house/pet sittings and drop-ins all week. Guaranteed evenings and flexible during the daytime. Let's chat and coordinate the best care for your pet! I come to your home so your cat can stay in their own comfy space, sticking to their normal routine for feeding, litter, and playtime. I handle litter care thoroughly no matter the setup, and if your cat needs medication, I make sure it's given on schedule and exactly as instructed. I pay close attention to how your cat's doing — energy, appetite, mood — and I'll send you updates and photos so you're never left wondering. And of course, I always tidy up before I go, so you come home to a happy cat and a clean space!
“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.”
“Jewel was a perfect pick for our dogs! She was very considerate and did a wonderful job caring for them during our vacation and we wouldn't hesitate to book her again!!!”
“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!!”
“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!”
The median cost per night for house sitting in Winnetka is $50
Pet parents share their Rover experiences - Winnetka
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 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 7,735 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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