Dog Sitting Winnetka

Book a Winnetka dog sitter to watch your dog in your sitter’s home or yours.

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Over 9
pet parents in Winnetka have booked dog sitting

Winnetka, Find top rated dog sitting

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

1 / 1
Sitter Profile Image: Aleksandra K.
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Aleksandra K.
from
$25
per visit
4.9 out of 5 stars
13 reviews
2 repeat clients
10 years of experience
Winnetka, IL, 60093

Did a good job with our three boys.

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Matt I.
Sitter Profile Image: Signe D.
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Signe D.
from
$15
per visit
5.0 out of 5 stars
12 reviews
6 repeat clients
15 years of experience
Evanston, IL, 60201

Absolutely great with my pup! Will definitely ask her to walk him again! he loved her!

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Jessica C.
Sitter Profile Image: Michelle M.
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Michelle M.
from
$25
per visit
5.0 out of 5 stars
70 reviews
24 repeat clients
10 years of experience
Glencoe, IL, 60022

Michelle was great with our cat! She was super communicative and punctual with her visits. She gave our cat all the attention she so desperately wanted, and left everything just as it was when we left. I would absolutely recommend her to anyone and hope we can work with her again!

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Makenzie G.
Sitter Profile Image: Ahmed L.
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Ahmed L.
from
$15
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
6 years of experience
Morton Grove, IL, 60053

Ahmed was very responsive, followed all instructions exactly, and provided plenty of picture and video updates. Also my dog loved him! Would definitely recommend.

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Jason B.
Sitter Profile Image: Ryan O.
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Ryan O.
from
$30
per visit
5.0 out of 5 stars
13 reviews
4 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: Leah G.
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Leah G.
from
$25
per visit
5.0 out of 5 stars
47 reviews
19 repeat clients
8 years of experience
Morton Grove, IL, 60053

Leah was prompt with her check in and check out times and continually sent us pictures from each visit and an update as to what she did. On her initial visit to meet our 2 cats, one of our cats was a little moody that day and wasn't interested in meeting Leah. But by the second day Leah told us that that particular cat was her new "bestie". The cats were well cared for and everything was done that was noted to be done.

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Kathy F.
Sitter Profile Image: Stephen M.
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Stephen M.
from
$34
per visit
5.0 out of 5 stars
40 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: Yao Q.
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Yao Q.
from
$17
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
4 years of experience
Morton Grove, IL, 60053

About: I’ve had a passion for animals since I was a little girl. I get along with all my neighbors’ dogs and my neighbors rely on me to take care of them some times. My old roommate has a golden retriever and I love taking care of him, giving him a bath and walking him. I have two cats at home and I even taught them some tricks! I’m currently working part time only on Mondays and Thursdays. So I have lots of free time outside of work taking care of your dogs and playing with them! I also have a car so I can drive to wherever you are and take your dogs for a walk where they are the most comfortable with. I live right next to the bike trail and woods, which is a paradise for dogs! If you have an athletic or active dog, I’ll take your dog running the trails, swimming in the pond, and have all the fun in the outside world! If your dog is less active, I’ll give your dog all the comfort and love at home, making sure they are well fed and entertained.

Sitter Profile Image: Angie F.
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Angie F.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
5 years of experience
Winnetka, IL, 60093

About: I’ve had dogs my entire life and have extensive hands-on experience caring for dogs of various breeds, sizes, and temperaments. Growing up with dogs has given me a strong understanding of their daily needs, behavior, exercise routines, and overall care. Over the past two years, I’ve also expanded my experience by professionally caring for other families’ dogs, including large breeds. My responsibilities have included walking, feeding, playtime, maintaining routines, providing companionship, and ensuring each dog feels safe, loved, and well cared for. I’m comfortable handling larger dogs with confidence and patience, and I’m committed to providing dependable, attentive care tailored to each pet’s individual needs. I’m currently studying full time. But during the day I have enough time to take care of pets in differents times of the day. I'm looking for pet care in the customers' house. This way I can make sure that the pets are comfortable and safe in the place where they live. Sometimes when they are transferred to another place they can suffer from stress or anxiety

Sitter Profile Image: Rhea S.
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Rhea S.
from
$17
per visit
5.0 out of 5 stars
2 reviews
3 years of experience
Morton Grove, IL, 60053

About: I love all animals and treat them with the respect they deserve. Dogs are definitely my spirit animal. I really enjoy taking care of pets and playing with them! :) I am a summer camp counselor which leaves my nights and weekends free. I wouldn't want to spend my free time doing anything else. I love spending time with animals! :) I will be gentle with your pet and firm when necessary. I adore animals and treat every one with respect and care. I will make sure everything is clean and as it should be! :)

Sitter Profile Image: Riley K.
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Riley K.
from
$22
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
6 years of experience
Evanston, IL, 60201

About: I have been pet-sitting for 6 years; caring for animals is my passion! My style of sitting is treating every pet as if it’s my own😊🐾 I am currently working a part time job, so I won’t be available 24-7—but I am more than happy to work with you on times to be there for your pets :) Please book with only serious inquiries😊 In my clients home, I will follow all rules and guidelines relating not only to their pet, but also to respecting their space as well.

Sitter Profile Image: Elizabeth T.
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Elizabeth T.
from
$20
per visit
2 years of experience
Glenview, IL, 60025

About: I've always loved caring for dogs and enjoy getting to know each pet's unique personality. I have experience caring for dogs of all sizes and ages, from tiny breeds and small dogs to large breeds, including pit bulls, as well as energetic puppies. Whether your dog loves long walks, playtime, cuddles on the couch, or simply sticking to their daily routine, I'm happy to provide the care they need. I've provided overnight house sitting for families, cared for pets in their own homes to help keep their routines consistent, and offered drop-in visits and dog walking. I'm comfortable handling dogs of all sizes, temperaments, and energy levels, and I understand that every dog has unique needs and deserves patient, individualized care. I know how important it is to trust the person caring for your pet, so I'll always treat your home with respect and your dog like they're part of my own family. I'll keep you updated with photos and messages while you're away, giving you peace of mind that your furry family member is safe, happy, and receiving plenty of love and attention I am a full-time kindergarten teacher, and caring for others is a big part of who I am. My job has taught me patience, responsibility, and the importance of creating a safe and loving environment — qualities I bring into caring for pets as well. Outside of school, I have time for early morning walks, check-ins, evening visits, and overnight stays. I truly enjoy spending my free time with animals and making sure they feel comfortable, happy, and cared for while their owners are away. I’m happy to follow each pet’s routine and give them the attention, exercise, and love they need. I treat every pet like they are my own and want them to feel safe, comfortable, and loved while their owners are away. I make sure to follow their normal routines, including feeding, walks, potty breaks, playtime, and any special instructions you provide. I have experience caring for dogs of all sizes, from puppies and small dogs to larger breeds, including pit bulls. I enjoy getting to know each dog’s personality and making sure they get the attention, exercise, and care they need. I’ll also keep you updated with pictures and messages so you can feel confident your pet is in good hands.

Sitter Profile Image: Chia Ping L.
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Chia Ping L.
from
$23
per visit
3 years of experience
Skokie, IL, 60077

About: I have a flexible schedule and can easily fit cat care into my daily routine. I’m available for drop-in visits and can provide feeding, fresh water, litter box cleaning, playtime, and companionship. I’ll follow your cat’s routine and send regular photo updates so you can have peace of mind while you’re away. Your cat’s safety and comfort are my top priorities. I’ll carefully follow all of your instructions, including feeding schedules, administering medications (if needed), and providing any special care your cat requires. I always make sure doors and windows are secure, keep the litter box clean, and provide a calm, stress-free environment. As a cat owner myself, I understand how important it is to earn your trust, and I’ll care for your cat as if they were my own. I’m currently a freelancer, which gives me a flexible schedule. I usually prefer afternoon visits because my meetings are typically finished by then, but I’m happy to accommodate morning visits too. I just ask for at least 3 days’ notice for morning bookings so I can plan my schedule accordingly. Your cat’s safety and comfort are my top priorities. During every visit, I’ll follow your care instructions carefully, including feeding schedules, fresh water, litter box cleaning, playtime, and administering medication if needed. I’ll make sure all doors and windows are secure before I leave and keep your home clean and tidy. As a cat owner myself, I understand that every cat has a unique personality, so I’ll respect their boundaries while making sure they feel safe, comfortable, and well cared for. I’ll also send regular photo updates so you can have peace of mind while you’re away.

Sitter Profile Image: Jennifer D.
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Jennifer D.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
45 years of experience
NORTHBROOK, IL, 60062

About: I’ve taken care of dogs since I was a kid. I would care for my neighbors animals when they were out of town. I’ve always loved dogs and have a 7 yr old Labradoodle, Max, that I rescued when he was a four month old puppy. He had escaped from his original owners and was missing for two days. When the police found him, he had been run over by a car. They couldn’t save his leg so he’s a tripod. He doesn’t even know he’s missing a leg. Max loves walks, water, and playing with his best doodle friend, Molly. I also have a lot of experience administering insulin shots for dogs. I would love to care for your fur babies the way I care for mine. I am semi retired and my time is very flexible. I’m available for daily walks or pet sitting. I’ll care for your fur baby exact same way I care for mine. My dog Max is living his best life with me. He receives lots of love, walks, snuggles, and playtime. I would give your dogs the same care and affection.

Sitter Profile Image: Jon E.
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Jon E.
from
$30
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
27 years of experience
Wilmette, IL, 60091

About: I love animals. Growing up with pets of all kinds I learned to appreciate them and recognize their needs. I know the importance of bonding with them and find great joy in forming that bond. I did domestic care for four years and my primary job was tending to the animals. I am trustworthy and caring and I will put the needs of your pet first. Every time. I have made pet care my priority. I presently work full time in pet car. I also love pet photography and offer that as a service I am available on a drop-in basis and I can make myself available for overnights and extended stays as well. Whatever you need, don't hesitate to ask. I have cleared my schedule to make myself available to tend to dogs and cats full-time. I will walk your dog or simply hang out with your pet, whichever you need. I will build a trust with you, and your pet will know. I look forward to meeting you. I am very conscientious and responsible. I lost my own dog of 14 years and this has opened the door for me to be able to tend to your dog or cat. I can only offer the same loving care that I showed my own dog.

Sitter Profile Image: Marissa H.
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Marissa H.
from
$18
per visit
5.0 out of 5 stars
7 reviews
4 repeat clients
20 years of experience
Evanston, IL, 60201

About: I ensure they receive the attention and provide expert supervision and ensure that every dog receives the highest level of and go beyond basic boarding by offering a variety of enrichment activities to keep your dog mentally and physically stimulated. From interactive toys and puzzles to group play sessions and nature walks, providing a range of activities to keep your dog happy and engaged. Clean and Safe Facilities: I follow strict cleanliness protocols to prevent the spread of illness and ensure a comfortable stay for every guest. Communication and Updates: I understand how important it is to stay connected with your pet while you're away… regular updates and photos so you can see how much fun your dog is having during their stay I am available all the time. I am very flexible and take my job and care seriously! Any medications or food allergies will be given priority. I have a fenced in yard with security for my surroundings and your pets. I also have a large crate as well and try to ensure safety first

Sitter Profile Image: Natalie C.
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Natalie C.
from
$30
per visit
5.0 out of 5 stars
36 reviews
15 repeat clients
11 years of experience
Skokie, IL, 60077

Natalie took care of our dog Sophie over a long weekend. She did an excellent job! The dog had recent surgery and had some activity restrictions which Natalie followed very closely. She sent us texts, pictures and comments with each visit! This helped us to know that the dog is very well taken care of and the pictures showed us how happy she is. Natalie spent time and pet the dog with each visit. Upon our return we found a happy, and healthy dog. We are planning to use Natalie’s services again. We highly recommend Natalie! Thank you Natalie!

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Ganka M.
Sitter Profile Image: Coty C.
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Coty C.
from
$35
per visit
5.0 out of 5 stars
66 reviews
22 repeat clients
20 years of experience
Evanston, IL, 60201

Cody is amazing! She took the time to learn my dog’s specific needs and personality, and tailors her interaction with them. Her many years of experience with dogs was evident in the way that she cared for my senior dog’s needs and quirks. Aside from her professionalism (always on time, dependable, reliable, trustworthy), she is passionate about dogs, and my little one absolutely loved her! She went out of her way to make sure that my dog felt safe and happy while I was away, and sent me lots of cute pics. I can’t say enough great things about her. You will love her. I will definitely be rebooking her again!

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Nancy V.
Sitter Profile Image: Sadie M.
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Sadie M.
from
$20
per visit
5.0 out of 5 stars
2 reviews
1 year of experience
Wilmette, IL, 60091

About: I am currently a college student who loves animals. I have a dog and three cats at home, and I have volunteered at animal shelters in the past, so I’m very experienced with pets. While I am newer to house sitting, I am definitely not new to loving and caring for our furry friends! I work part time so I am available multiple times every day. I can stop by homes in the morning before work, and then after work in the afternoon and evening. I walk my dog and he loves our fenced in yard. I also am accustomed to feeding and cleaning litter boxes. And of course, care, love and attention are important every day!

Sitter Profile Image: Michelle B.
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Michelle B.
from
$15
per visit
5.0 out of 5 stars
4 reviews
3 repeat clients
15 years of experience
Glenview, IL, 60025

Very kind, thoughtful, and patient with our crazy puppy Shilo. Thank you, Michelle!

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Emily Y.
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The median cost per visit for dog sitting in Winnetka is $20

Dog parents share their Rover experiences - Winnetka

1 / 1
5.0 out of 5 stars

Jiayi was incredibly professional, courteous, and worked so well with our dog! I would absolutely recommend her and will definitely try to book Jiayi again.

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Robert M.
Drop-In Visits
5.0 out of 5 stars

Melisa always goes the extra mile. She cared for our two elderly Chihuahuas for a long weekend. Handled meds, feedings and cleanup like a star.

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Paul S.
Drop-In Visits
5.0 out of 5 stars

The best pet sitter. Rosy literally just saved my cat’s life, when she noticed he was not his usual self, took him to the vet, where they identified he had a urinary blockage and likely just hours to live. How lucky for us that Rosy was caring for our animals and so observant. Thank you, forever. 🌟🌟🌟🌟🌟

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Kim C.
Drop-In Visits
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

Donna was wonderful! She texted pictures and updates every time she was here. Henry really liked her, and he was well taken care of. It gave me peace of mind knowing that he was happy. I would hire Donna again any time.

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Marjorie A.
Drop-In Visits
4.0 out of 5 stars

There was one missed visit out of 5. Taylor was apologetic & took care of the dogs as scheduled for the rest of the visits.

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Marilee E.
Drop-In Visits
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Sitters in Winnetka average 7
repeat dog sitting clients

FAQs for Drop-In Visits - Winnetka

Frequently asked questions about Rover

The average cost for Dog Sitting in Winnetka on Rover is $22.2 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog 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 Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 11,741 sitters on Rover offering Dog Sitting across Winnetka. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winnetka stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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!

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 .

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.

A Meet & Greet is a short introductory meeting between you, your dog, 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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Winnetka with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Winnetka. On Rover:

  • 91% of sitters can help with special care needs
  • 95% 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.

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.

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