Dog Sitting in Winnetka

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

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Top rated Winnetka dog 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: Signe D.
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Signe D.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
9 reviews
4 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
67 reviews
23 repeat clients
10 years of experience
Glencoe, IL, 60022

Michelle M. is awesome! She was great with our English Mastiffs, managed to help us bathe them despite their hyped-up state. She's very personable and easy to relate to as well. We look forward to having her housesit for us in the future. Thanks, Michelle!

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

Adam was great! His updates were informative and took very good care of our cat. He was flexible with time and was able to squeeze in an extra visit at the last minute.

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Brad R.
Sitter Profile Image: Lauren & Lauren P.
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Lauren & Lauren P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
166 reviews
32 repeat clients
4 years of experience
Northbrook, IL, 60062

Beyond grateful that I connected with Lauren and Lauren, and they could help with our cat while our entire family traveled together. Communication is always quick, clear, and helpful. They flagged every visit, and kept me updated with all the details from each house visit for our cat. Will absolutely keep them at the top of the list for any future needs!

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Megan H.
Sitter Profile Image: Leah G.
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Leah G.
from
$25
per visit
5.0 out of 5 stars
43 reviews
14 repeat clients
8 years of experience
Morton Grove, IL, 60053

Leah was great! It was wonderful to have someone who overthought feeding my boys and making sure they got their medicines. One of my boys is super shy and she took the time to find his hiding spots to check on him and even sat near by to lure him out. My other guy got lots of attention as well. Leah also went beyond cat sitting to water the plants, bring in the mail and brought in the trash cans from the curb.

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Katie R.
Sitter Profile Image: Debbie K.
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Debbie K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
51 reviews
20 repeat clients
20 years of experience
Skokie, IL, 60077

Really great and attentive will definitely ask to help out again

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Stephen S.
Sitter Profile Image: Jake L.
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Jake L.
from
$10
per visit
4 years of experience
Northbrook, IL, 60062

About: I’ve been around dogs and cats all my life, recently worked with animals as big as horses and cows, to chickens and ducks. Friends and family trust me with their animals! My schedule is currently free, weekdays and weekends and nights! I am willing to work holidays. I will also walk in any type of weather! I have a fenced in backyard, with 2 very friend dogs for yours to play with! I do have crates (if needed) and lots of treats!

Sitter Profile Image: Marissa H.
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Marissa H.
from
$18
per visit
5.0 out of 5 stars
7 reviews
3 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: Mia W.
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Mia W.
from
$25
per visit
5 years of experience
Wilmette, IL, 60091

About: I have experience working with cats and dogs. My family adopted a cat a few years ago and she quickly became part of the family. I have experience walking my neighbors dogs and know how to tame a dog if need be. Working with cats and dogs is a passion of mine as each has their own unique personality that is discovered over time. I am a college student at the Royal Conservatory of Music Glenn Gould School. I am available most afternoons Monday to Saturday, except for Sunday. I have a large fenced backyard that is safe for dogs to soak up the sun while having fun exploring, running around, and playing games

Sitter Profile Image: Parisa H.
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Parisa H.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
94 reviews
25 repeat clients
10 years of experience
North Park, Chicago, IL, 60659

Parisa did a fabulous job taking care of our pet bunnies. She followed all the instructions and took a great care of our bunnies. She is detailed oriented, caring and a very punctual. We would definitely reach out to her again in the future. Totally recommend her.

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M E.
Sitter Profile Image: Eileen H.
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Eileen H.
from
$15
per visit
3 years of experience
Wilmette, IL, 60091

About: I have cared for dogs of all ages since I was a young child, especially dogs of older ages. Working with animals genuinely makes my day. I am currently home from college so I currently have a very open schedule. I like to stay active, so walking with your pet will fit right into my routine! My dog, Porky, has been cared for in my home for the past fourteen years. I have learned from my mom how to properly care for dogs.

Sitter Profile Image: Erin R.
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Erin R.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
17 reviews
5 repeat clients
10 years of experience
Highland Park, IL, 60035

Erin did great taking care of Olive!

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Ellyse T.
Sitter Profile Image: Ruby A.
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Ruby A.
from
$13
per visit
4 years of experience
Skokie, IL, 60076

About: I have dogs at home, so I’m very comfortable caring for them and understanding their needs. I’ve also helped house sit with my mom, taking care of dogs by feeding, walking, and giving them lots of attention. I’m reliable and genuinely enjoy being around animals. Pet care fits easily into my daily routine since I’m used to being around and caring for animals. I plan my schedule so I have plenty of time for feeding, walks, playtime, and check-ins. I’m reliable with routines and make sure pets get consistent care, attention, and exercise throughout the day. I follow each pet’s routine closely to keep them comfortable, whether I’m in my home or a client’s home. I make sure they’re fed on schedule, get plenty of exercise and playtime, and have lots of attention. I also keep their space clean and safe, and I always follow any specific instructions the owner provides.

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

Paige is FANTASTIC! My dogs loved her the minute they met her. She took great care of them and communicates well. I had no worries at all going away and leaving my 2 Danes in her care! She’s definitely added to the top of our pet sitter list!

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Jahmila S.
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: Andrew G.
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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: Riley K.
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Riley K.
from
$15
per visit
5.0 out of 5 stars
4 reviews
6 years of experience
Evanston, IL, 60201

About: I have been pet-sitting since I was 14, due to the population of dogs in my neighborhood. My community has trusted me with their fur babies, and I’m certain we will have so much fun!😊 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: Maggie J.
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Maggie J.
from
$17
per visit
11 years of experience
Winnetka, IL, 60093

About: I have always had at least 2 animals in my house, which helped me learn how to be responsible at a young age. Then when I was older, I would help me neighbors and other friends when they went out of town, so I have been taking care of dogs/cats for a while! I am in college right now, so I will have some spare time to stop by/walk dogs. My class schedule is spread out nicely, so I will have more than enough time and flexibility. I will help your pets in your home, and try to follow their normal routine. I can crate, feed, walk, play, anything you could ever need!

Sitter Profile Image: Karissa D.
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Karissa D.
from
$30
per visit
15 years of experience
Winnetka, IL, 60093

About: I’ve cared for animals most of my life. I had a cat for 15 years and a puppy for several years growing up. I’m comfortable with different ages and personalities, and I always treat pets with the same patience and love I’d want for my own. I work from home full-time, which gives me a flexible schedule and allows me to provide attentive care throughout the day. I’m available for doggy daycare during working hours, including regular potty breaks, playtime, feeding, and companionship. I’m also available for walks and drop-in visits after 5:00 PM on weekdays. With me, pets get a calm, safe, and welcoming space. I’ll make sure they have plenty of attention, regular potty breaks, playtime, and a cozy spot to relax. I follow your pet’s routine closely so they feel comfortable and at ease.

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

If I could give seven stars I would give this Cat Sitter seven stars we had a list of instructions five pages long and she filed everything every single instruction to the letter so our cat looks so great and healthy after being alone for four days so I am just thrilled at this Cat Sitter I cannot recommend her enough

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Michael L.
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Winnetka dog parents share their Rover experiences

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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
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How Rover works

  1. 1. Search

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

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs 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!

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Dog Sitting FAQs

Frequently asked questions about Rover

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

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

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.

Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Winnetka.

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

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

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

Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.