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!”
“Em was so good with our dog Tessa and I plan to use her again. She was very professional from the beginning. She sent pictures every day and communicated with us to let us know what was going on at home and with our dog. She was a great caretaker for our old dog.”
“Katie was absolutely amazing! Both of my dogs loved her, but she was especially wonderful with Bella. Bella can be very scared and gets sad when we leave, so Katie was quick to make sure she was eating, gave her extra attention, and made sure she was comfortable and feeling loved. That meant so much to me and gave me such peace of mind while we were away. ❤️Great at communicating, sent lots of pictures and updates, and made sure both dogs got treats, walks, playtime, and plenty of attention. I would absolutely book with her again and truly can’t say enough great things about her. She went above and beyond!”
“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.”
“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 many pets so i’ve been taking care of them since I was very young. I’ve been dog and cat sitting for others for about 4 years now from all different ages ranging from a puppy to an elderly dog. I have a rabbit so Id be happy to rabbit sit! 🐰 I’ve also taken care of a bearded dragon! I’ve administered medication when needed such as insulin to dogs. Pet sitting fits into my daily routine through out the week from the morning time and afternoon time as well. I’m also free on weekends! I create a comfortable and loving environment in owners home so that your pet doesn’t get stressed while away. I keep their normal routine with feedings and walkings as well.
“Alanoud came to our house to help one busy evening for a few hours. It happened to be pouring rain, but she took care of our big, rambunctious pup in good cheer nonetheless. I'm feeling quite confident about having her stay at our home for a few days while we attend a wedding out of town later this month.”
“Jamie is simply and absolutely the best. Period end of story! Not only would we highly recommended her in a instant but we would not go with anyone else. We know there are a lot of good pet sitters but we have no reason to go with anyone else but Jamie. Jamie is genuinely compassionate and noticeably very caring and most of all she had fun taking care of our loved one. Thank you Jamie. You are now part of our family.! We are very grateful to you.”
“Renee is great. Simple as that. Our sometimes tweaky, neurotic terrier, Molly, loved every minute with her housesitter. Renee was thorough, attentive, playful, and giving. She went above and beyond to ensure Molly got all the snuggles, walks, required meds, and love she so needs. I don’t think she wanted her week with Renee to end. Renee is personable, on top of things, and clean. Was my home cleaner when I got back? Holy cow, it was. Thanks Renee. Book her now before I do, again and again.”
About: I've always had dogs my whole life. Friends and family can always rely on me to take care of their pets or check in on their pets whenever they are out of town or busy at work. I will feed, walk, and play for however much time is needed. I currently work early mornings but there is someone always at the house to feed, play and keep your furry friends company! My whole day after work is completely open so I can't wait to take care of them. Huge fenced yard as well as a my own pet to play with your furry friend if needed. Plenty of toys to keep them occupied as well as plenty of treats to spoil them.
“Bridget was the best dog sitter we have ever had (that is saying a lot because we have had him for 11 years)! She communicates with us the whole time and sent a ton of great photos. Our dog has some special needs (arthritis and doesn’t love other dogs) and she handled it perfectly. We will book her for all future vacations and dog walks.”
About: My cousin goes out of town often, so I would stop by her house to check on her dogs (feeding, playing, taking them out for walks, and changing out the pee pads). I also helped care for my roommate’s dogs/puppy. Additionally, I’ve volunteered for dog walks from a local dog shelter! I love taking dogs on walks and hikes to keep them active! I’m a nurse, so I only work 3 nights a week (7pm-7:30am). I have more than half the week available to walk/play/take care of your pets! This also means I am available in the mornings after a shift, as well. Although my work nights vary weekly, I am more than happy to coordinate our schedules that work best for you :) I live close to a lot of forests, trails, and parks, so your pup will have a wonderful time staying active outdoors! I am very attentive to details and will adhere to specific dietary needs!
About: My daughter and I have been boarding dogs for years and love it, we really focus on one families pet at a time so we give him/her our full love and attention. We will take up to 2 dogs at a time. We love to walk and play with the dogs. We have a large fully enclosed back yard in addition to a park at the end of our block we can walk dogs around a large walking path. We text photos and funny videos of us with your pet. My daughter is off to college this year and this will assist her school fund. We love these dogs as if they were our own. WE love taking care of pets, We love staying active walking and playing with the dogs. We will not take dogs if we do not have time for them. I have an enclosed back yard that is perfect for active dogs to chase birds and have a bit of an area to run free. We do walk the dogs to our local park at the end of our block.
“Ali did a great job with my pugs! They sent lots of pictures and my dogs were well-cared for and able to stay in their familiar environment. They were punctual and a great communicator. I would use their services again”
“We had a wonderful experience with Ariel! She was extremely responsive and communicative throughout our time away, which gave us so much peace of mind. She took excellent care of our animals and treated our home with great care as well. Everything was just as we left it, and our pets were clearly happy and well-loved. We would highly recommend her to anyone looking for a reliable, thoughtful pet sitter and absolutely plan to use her services again.”
“Great as always! It’s comforting to know my boys are in good and caring hands with Michelle when I have to leave them. Good communication with pictures and lots of walks and play! Would recommend for others in need of house sitting or dog walking.”
The median cost per night for house sitting in Winnetka is $50
Pet parents share their Rover experiences - Winnetka
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.
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.
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.
How to book house sitting
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 of House Sitting in Winnetka is $67 per night as of October 2026. Most bookings cost between $27 and $100 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 7,603 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winnetka. On Rover:
- 87% of sitters can help with special care needs
- 92% can help with giving oral medications or injections
- 95% 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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