Pet Sitting in Winnetka

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winnetka pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Donna C.
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Donna C.
Star Sitter
from
$29
per visit
5.0 out of 5 stars
571 reviews
136 repeat clients
40 years of experience
Wilmette, IL, 60091

Donna is fabulous. I have a nervous little chihuahua and she is so gentle and loving with her. She goes above and beyond and even takes her to work with her to make her feel comfortable. I don’t trust a lot of people with my dogs, but I trust Donna!

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Lauren G.
Sitter Profile Image: Rebeca A.
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Rebeca A.
from
$20
per visit
5.0 out of 5 stars
4 reviews
15 years of experience
Wilmette, IL, 60091

Absolutely recommend Rebeca! You can tell she really cares about dogs and loves what she does. My dog Snoopy has anxiety & is very shy at first but he felt at ease with her as soon as he met her during the meet and greet. She was so gentle, patient & sweet with him right away. I felt completely at ease knowing he was in such caring hands. I will def be booking with her again!

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Elaine D.
Sitter Profile Image: Madeline I.
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Madeline I.
from
$17
per visit
5.0 out of 5 stars
3 reviews
3 repeat clients
3 years of experience
Wilmette, IL, 60091

About: I’ve been around dogs my entire life, mostly chihuahuas and rescues, so I’m very comfortable with pups who need a little extra patience, reassurance, or understanding. My hands-on experience goes far beyond casual pet care. At Miami University, I was part of Paws for a Cause, where we helped train dogs to prepare them for working with children or future companion roles. This gave me a strong foundation in obedience training, reading body language, and supporting dogs with different temperaments. More recently, I’ve been volunteering with the Evanston Animal Shelter, working with dogs who have a wide range of behaviors and needs. There, I’ve assisted with medication administration, training sessions, enrichment, and helping nervous or high-energy dogs feel more comfortable and confident. I’m also on a path toward becoming a Physician Assistant, which adds to my calm, attentive, and health-focused approach. I’m comfortable managing routines, monitoring for changes, and making sure each dog feels safe and cared for. Overall, I bring a mix of lifelong experience, formal training exposure, shelter work, and genuine love for dogs of all personalities. Your pet will be treated with patience, structure, and plenty of affection. I work full-time as a medical scribe during the day (9–5), so evenings, weekends, and holidays are when I’m most available for pet care. During those times, I’m fully focused on your pet’s needs—whether that’s walks, playtime, feeding, or just keeping them company. My schedule outside of work is very flexible, so I can reliably fit in consistent visits or longer stays. When I’m caring for pets in a client’s home, I follow their normal routine as closely as possible—feeding schedules, walk times, crate routines, and any training cues you use. I take time to get to know your pet’s personality, comfort level, and boundaries so they feel safe and relaxed. I provide plenty of attention, enrichment, and calm companionship, and I always keep water fresh, watch for behavior changes, and send regular updates so you feel connected. If I’m hosting in my home (or doing extended stays), I make sure pets have a quiet, clean space to settle in, regular potty breaks, structured playtime, and a consistent routine. Safety is a top priority, doors secured, no access to anything unsafe, and lots of supervised time. Whether I’m in your home or mine, your pet gets patient, reliable care with the goal of making them feel comfortable, understood, and well-loved.

Sitter Profile Image: Ella V.
Verified Background Check
Ella V.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
268 reviews
117 repeat clients
15 years of experience
Winnetka, IL, 60093

Ella is terrific! She always arrived on the scheduled visit times and shared photos with us from her drop-in visits. This was our first time using Rover and the first weekend our new kittens have had a kitty sitter. Everything went great and we will definitely look for availability with Ella for future visits.

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Joseph y.
Sitter Profile Image: Andrew N.
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Andrew N.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
61 reviews
18 repeat clients
15 years of experience
Evanston, IL, 60201

Andrew was wonderful. My two standard Poodles liked him right off the bat. He was communicative, punctual and always happy with a smile on his face even when it rained.

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Tanya H.
Sitter Profile Image: Cicely B.
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Cicely B.
from
$20
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Winnetka, IL, 60093

Riley loved it! Thanks for coming over!!

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Jeff U.
Sitter Profile Image: Adam H.
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Adam H.
from
$17
per visit
5.0 out of 5 stars
75 reviews
17 repeat clients
45 years of experience
Evanston, IL, 60201

Amazing service as usual! It wasn't until the day after we left for our trip when I realized that I missed a day on the initial booking. Adam was more than willing to go in that day with no notice so our cats wouldn't go a day without food. Thank you Adam, we are so grateful!

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Brad R.
Sitter Profile Image: Isabela B.
Verified Enhanced Background Check
Isabela B.
from
$17
per visit
5.0 out of 5 stars
22 reviews
9 repeat clients
15 years of experience
Glenview, IL, 60025

Isabella has been wonderful and adapted to my flight changes during the government shutdown. She took get care of my fur baby and will definitely be using her in the future!!!

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Cheryl B.
Sitter Profile Image: William G. H.
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William G. H.
from
$18
per visit
5.0 out of 5 stars
23 reviews
9 repeat clients
50 years of experience
Wilmette, IL, 60091

Bill was great with our 2 labs. He is clearly a dog lover. We look forward to using him for our dog care needs!

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Emily L.
Sitter Profile Image: Keeley V.
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Keeley V.
from
$20
per visit
5.0 out of 5 stars
11 reviews
2 repeat clients
15 years of experience
Wilmette, IL, 60091

Keeley was great. She accepted my last minute booking, sent lots of pictures and videos, and gave my cat lots of love.

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Ann D.
Sitter Profile Image: Stephen M.
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Stephen M.
from
$29
per visit
5.0 out of 5 stars
39 reviews
16 repeat clients
15 years of experience
Winnetka, IL, 60093

Stephen and Donna did an excellent job walking our Great Pyrenees mix several times over a few weeks. You could feel their love for dogs from the moment we met them and they were very communicative and kind throughout the whole process. Our boy enjoyed and looked forward to his walks with them and we would definitely recommend and use their services in the future.

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Denise M.
Sitter Profile Image: Jason A.
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Jason A.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
79 reviews
20 repeat clients
25 years of experience
Winnetka, IL, 60093

Jason is great with our pups so we hired him for a week stay…

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Melissa D.
Sitter Profile Image: Paige F.
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Paige F.
from
$25
per visit
5.0 out of 5 stars
35 reviews
14 repeat clients
7 years of experience
Glenview, IL, 60026

Paige did a wonderful job. She was prompt and quickly built trust with Maggie. Great visit cards and updates. Will definitely book with her again.

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Melissa A.
Sitter Profile Image: Ryan O.
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Ryan O.
from
$30
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
10 years of experience
Northfield, IL, 60093

Responsible and great to work with as always!

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Rory B.
Sitter Profile Image: Anna D.
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Anna D.
from
$20
per visit
4.9 out of 5 stars
36 reviews
15 repeat clients
16 years of experience
Winnetka, IL, 60093

Anna took care of my two pups while I was out of town. They are 14 and 11, so it made us feel much more at east to know they were comfortable in their own home in Anna's care. She communicated with us regularly and sent photos of the pups enjoying their meals. Anna even took in packages for me and kept an eye on the house. We would definitely use her again and highly recommend her to anyone.

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Tara L.
Sitter Profile Image: Mengchi P.
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Mengchi P.
from
$20
per visit
18 years of experience
Evanston, IL, 60201

About: I love making friends with doggies and cats. i love taking picture of them while spoiling them with their favorite toys, treats, couches and so on. I am currently a graduate student at Northwestern University and work part time on digital marketing consulting. I have very flexible schedules and home most of the time. i have a large fenced in backyard and I love taking dogs for a nice long walks! I love spoiling them with all the comfy beds/chairs and treats!

Sitter Profile Image: Samantha L.
Verified Background Check
Samantha L.
from
$30
per visit
5.0 out of 5 stars
47 reviews
23 repeat clients
10 years of experience
Wilmette, IL, 60091

About: Ever since I was a child, I have had a passion for dogs and animals of all sorts. Growing up in the Philippines, my relatives found it strange to have such compassion for animals. I'd always begged my parents for a dog while doing avid research and volunteering at pet-related jobs to prepare myself if my dream was to come true. When I was 17, my parents finally agreed to get a dog-- but not just any dog. I wanted my dream dog: an Alaskan Malamute. Huge, stubborn, and a daily shedder, it was a huge challenge I took on myself. However, this Malamute was well trained, house-broken, and friendly. I believe I can take care of a dog of any size, temperament, or history. I am a graduate from the University of Illinois in Chicago with a Bachelor’s Degree in Biology/Sociology. I volunteered at the Chicago Canine Rescue downtown where we play and walk with shelter dogs. I have copious experience with boarding, walking, and overall loving dogs. As a past dog boarder, I understand the care and attention that must be given to a pup to create a trusting bond with them. For more pictures of our past clients and to get a better idea how I interact with your pup, check out this instagram: powerpuffdogs May have to step out a few times a day, or if I have an outing I would make sure your pup has had plenty of exercise and pets before leaving. I adhere as closely as possible to the pet’s existing schedule— routine is key! Other than that, if you are comfortable with it, I can take your dog on forest walks, dog parks (only if you’d like, and with ample supervision), or on play dates with my own well-socialized dogs!

Sitter Profile Image: Sidney P.
Verified Enhanced Background Check
Sidney P.
from
$30
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
15 years of experience
Winnetka, IL, 60093

About: Hi! I’ve been a lifelong animal lover, and I’ve had pets all my life — so I know how much pets mean to their families. My girlfriend introduced me to Rover, and since then, I’ve been all in. I currently walk up to 10 dogs a day and board around 2 dogs each month, and I truly enjoy every minute of it. Whether it’s a high-energy pup who needs long walks or a shy cat who just wants a quiet companion, I treat every pet like my own. I know how important trust is when it comes to pet care, and I always go the extra mile to make sure your furry friend feels safe, happy, and loved while you're away. I’d love the chance to meet your pet and give them the care and attention they deserve! Pet care is a major part of my daily routine. I work in real estate, which gives me a flexible schedule and plenty of control over my time. This flexibility allows me to dedicate consistent blocks of time each day to walking dogs, doing drop-in visits, and boarding pets comfortably in my home. Whether I’m caring for pets in my home or in a client’s home, safety and trust always come first. In my home, I create a calm, clean, and pet-friendly environment. I make sure there are no hazards within reach, keep any unfamiliar pets separated as needed, and provide plenty of space for relaxation, play, and personal time. I follow any routines or rules you provide so your pet feels comfortable and secure—just like they would at home. When I care for pets in a client’s home, I treat it with the same respect and care I would my own. I follow all instructions closely, keep your pet’s schedule consistent, and provide regular updates so you can feel confident they’re in good hands. I’m always attentive to their behavior, energy levels, and comfort to make sure they’re safe and happy throughout the visit. Whether it’s walks, playtime, meals, or quiet companionship, I’m committed to providing a trustworthy, low-stress experience for both you and your pet.

Sitter Profile Image: Andrew G.
Verified Enhanced Background Check
Andrew G.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
233 reviews
75 repeat clients
20 years of experience
Winnetka, IL, 60093

Andrew has been a Godsend! I’ve taken Hudson to his home for day care and Hudson loves it! Andrew is so good with him and I’m so happy I found Andrew!!

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Melody E.
Sitter Profile Image: Camila V.
Verified Enhanced Background Check
Camila V.
from
$26
per visit
5.0 out of 5 stars
55 reviews
2 repeat clients
13 years of experience
Wilmette, IL, 60091

Can’t say enough good things about Camila. Quick to respond to my request, flexible to setup a meet and greet, great with the dogs, sent pictures and was very informative about how they were doing and arrived within the agreed upon appointment time. I would absolutely recommend her and use her again.

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Fina C.
1 / 1
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Over 61
pet parents in Winnetka have booked pet sitting

Winnetka pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Absolutely recommend Rebeca! You can tell she really cares about dogs and loves what she does. My dog Snoopy has anxiety & is very shy at first but he felt at ease with her as soon as he met her during the meet and greet. She was so gentle, patient & sweet with him right away. I felt completely at ease knowing he was in such caring hands. I will def be booking with her again!

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Elaine D.
Drop-In Visits
5.0 out of 5 stars

Rosy was communicative, attentive, and went above and beyond to make sure our cat and us were at ease and taken care of while we were away. We’ve booked Rosy twice now and will absolutely do so again in the future - absolutely 10/10.

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Shawn V.
Drop-In Visits
5.0 out of 5 stars

Donna was fantastic! Reliable, consistent, communicated well, and took great care of our precious cats!

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Stefan D.
Drop-In Visits
5.0 out of 5 stars

We love Kelly so much and feel comfortable traveling knowing Kelly has our fur babies taken care of! So grateful to have met her through Rover!

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Julie H.
Drop-In Visits
5.0 out of 5 stars

Kaitlin was very caring and attentive to our indoor/outdoor cats! She was able to connect with them quickly- even our very shy female- and made sure they had all they needed. She is very responsive and reliable, providing regular updates and quick feedback to any questions.

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Charlotte B.
Drop-In Visits
5.0 out of 5 stars

Katie is on time, responsible, easy to communicate! my cat loves her, she is very responsible of taking care of my kitty! Thank you very much Katie!

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Bellamy D.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for pet sitting in Winnetka is $20

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 pet 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.

Sitters in Winnetka average 7
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winnetka on Rover as of Apr 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Winnetka pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

As of Apr 2026, there are 2,659 pet sitters in Winnetka. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 86% of Winnetka pet sitters respond in under an hour.

Pet sitters in Winnetka have an average of 14 years of experience. Pet sitters with repeat customers have an average of 7 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winnetka.

Rover makes it easy to find Winnetka pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 2,659 pet sitters in Winnetka on Rover, so you’re sure to find the perfect match for your pet! In Winnetka, 94% of pet sitters offer daily exercise, 97% offer medication administration, and 90% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.