Pet Sitting Winthrop Harbor

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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pet parents in Winthrop Harbor have booked pet sitting

Winthrop Harbor, Find top rated pet sitting

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: Cynthia G.
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Cynthia G.
from
$15
per visit
5.0 out of 5 stars
• 4 reviews
1 year of experience
Pleasant Prairie, WI, 53158

“Absolutely wonderful with my boys while I was out of town. My nervous one was super comfortable with her, which is always huge for me. Lots of notes and pictures to keep me updated. Will definitely book again.”

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Erin M.
Sitter Profile Image: Jessika H.
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Jessika H.
from
$25
per visit
5.0 out of 5 stars
• 37 reviews
8 repeat clients
12 years of experience
Pleasant Prairie, WI, 53158

“I’ve used Jessika’s services a few times now and she’s always been so amazing with my boys. I genuinely get sad when she’s not available to watch them because they just adore her and are so comfortable with her. She gives them lots of attention and leaves very helpful visit notes so I know exactly what’s going on when I’m gone. I highly highly recommend her for anyone who needs a pet sitter!”

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Kris B.
Sitter Profile Image: Karen C.
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Karen C.
from
$16
per visit
4.0 out of 5 stars
• 2 reviews
2 repeat clients
2 years of experience
Pleasant Prairie, WI, 53158

About: My family used to own 7 dogs when I was a preteen! 6 were chihuahuas and one was a pit bull, so I feel comfortable with any dog size. I would feed, walk, wash, and play with them. Now, I help my friends with their dogs whenever it’s needed. I know when they need space and when they want to be playful. I have a lots of energy, so I can ply with your pup for a long time! I’m a full-time student and work part-time for two days a week, but it only takes up in the morning. On any day of the week, I am available at any time after 4pm, and before 11am except on Tuesdays, Fridays, and Sundays. I’m always observing, partially because of admiration, but also watching out for any signs of discomfort. I can recognize when they need space, are uncomfortable, anxious, or threatened. I’m cautious when it comes to interactions while walking and will walk across the other side of the street from another dog for precaution.

Sitter Profile Image: Christine S.
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Christine S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 9 reviews
6 repeat clients
30 years of experience
Gurnee, IL, 60031

“Christine was awesome! I have never had anyone that I didn't know watching my animals, so I was a little nervous. But she was great. My kitties LOVED her and it helped me enjoy my vacation more knowing they were being so well taken care of. My one cat has diabetes and she made sure to stay on schedule with his meds.I also got lots of pictures and updates for every visit. Highly recommend👍🏼😁”

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Madeline T.
Sitter Profile Image: Ethany I.
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Ethany I.
from
$25
per visit
4.0 out of 5 stars
• 4 reviews
2 repeat clients
13 years of experience
Zion, IL, 60099

About: I’ve taken care of dogs for over 13 years. I have 6 dogs of my own who are well cared for and get all of my love and attention. Dogs to me are like children who need to be well kept. I do my best to keep your fur friends happy as can be along with their owners. I do not discriminate against any breeds. I love and care for any animals as if they were all the same. I believe in quality service and I strongly recommend a person like me for the job. Things will get done Professionally and correctly. If any one has any questions or concerns I am free and willing to answer any of them at any time of the day. I am currently a college graduate looking for some extra side cash to save up for law school. I am currently a school bus driver for special needs children Monday through Friday. I have prior dog care experience. I my self care for six of my own dogs. I do not discriminate against size or breed of one’s animal. I quite honestly find joy in interacting with animals, it puts a smile on my face like no other job could.

Sitter Profile Image: Byron G.
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Byron G.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 60 reviews
21 repeat clients
4 years of experience
Waukegan, IL, 60087

About: From the beginning, my wife and I have shared a love for pets, especially dogs. I formed a home where our first child was a furry, four-legged friend. This beloved first canine child strengthened my love and taught me profound parenting skills, and I have passed that legacy on to our two teenage children and our three-year-old son. I formed a home where the love for our dogs is genuine and sincere. That's why caring for your puppies is my responsibility, and I take it very seriously. I have extensive experience caring for all types of dogs, breeds, and ages, and we carefully study their different and unique personalities and needs. I treat them with love and respect. From the moment your dog enters our home, he/she becomes another member of my family. Rest assured that he'll share unique and memorable spaces with each member of my family and will be a part of my family routine without exception. My home is a loving, personalized, safe, and warm home for your dog. Depending on your needs, I accommodate and strive to make our four-legged friend feel at home with us.

Sitter Profile Image: Victoria-Anna K.
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Victoria-Anna K.
from
$15
per visit
5.0 out of 5 stars
• 2 reviews
2 repeat clients
4 years of experience
Kenosha, WI, 53944

About: I’ve had pets most of my life… I’ve had dogs, cats, bunnies and guinea pigs. I’ve house sat which included farm animals. I am patient and willing to give all my love to any animal even if they aren’t mine. I am a student so I would come between classes, before classes, and after to take care of any pets. I do not have a full time job. I want to work with whatever you have at your house. I will make sure that all of your rules are followed, and that your fur babies are well taken getting care of.

Sitter Profile Image: Faith Q.
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Faith Q.
Star Sitter
from
$23
per visit
4.9 out of 5 stars
• 57 reviews
39 repeat clients
20 years of experience
Gurnee, IL, 60031

“Faith is fantastic. She is so attentive to detail and truly cares for animals. I am so grateful for her help this week on a last minute request. She is a life saver. Highly recommend!”

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Sophia G.
Sitter Profile Image: Nicholas K.
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Nicholas K.
from
$18
per visit
4 years of experience
Pleasant Prairie, WI, 53158

About: For the past 4 years, I’ve been the go to pet sitter for friends, family, and neighbors. I am an honest and hard worker and I provide good communication with my clients. I am a student at parkside with one year left until I graduate. With my schedule, I am able to pet sit during the day and overnight on weekdays and I’m fully available on weekends. When I’m pet sitting in a clients home, I spend the majority of my day there playing with and taking care of the pets. I put the pet’s needs first and maintain good communication with the owners to ensure their pet is taken care of properly. I treat the home with respect and ensure the owners of the home know my schedule so there are no surprises while I’m watching their pets.

Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$30
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
10 years of experience
Beach Park, IL, 60099

About: Hiya! My name is Jenny and I have a current dog whose name is Kaya. My husband and I just adopted her. She’s 6 years old. I always loved having dogs. They are a real blessing and can be one's best friend. I've potty trained them all and taught them how to shake, sit, turn, stay/wait, come. You know those people who go to parties and hang with the adults? Well you would find me with the dogs 🥳 I work from home most days. Just ask if you have any questions :) I will take dogs on walks during my lunch/break if weather permits I have a fenced yard. We have a good size backyard with a park nearby. With a lot of good walking areas to take them out.

Sitter Profile Image: Lexi P.
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Lexi P.
from
$45
per visit
2 years of experience
Zion, IL, 60099

About: Hi! I’m a veteran with a few years of animal care experience, and I’m currently pursuing a degree in animal sciences with a focus on animal health and behavior. Caring for animals is an important part of my life, and I’m excited to continue building my knowledge through both school and hands-on experience. My goal is to provide thoughtful, dependable care while helping your pet feel safe and comfortable when you’re away. I understand that every animal has their own personality and needs, and I’m happy to follow your pet’s routine and care instructions to give them individualized attention. Whether your pet enjoys active playtime or prefers quiet companionship, I’d love to get to know them and help you feel confident about their care! I’m an active person and a dog owner myself, so I understand how important it is to find someone you trust to care for your pets. I’m also a veteran, currently working from home while pursuing my degree full-time in animal sciences, with a focus on animal health and behavior. With a few years of animal care experience, I’m passionate about providing attentive, personalized care to every pet I meet. I have two dogs that are small and very polite. They are both neutered and spayed. For them the more the merrier. I couldn’t agree more. Your pets stay will be comfortable and active. I promise to make sure they are well taken care of and get lots of love and sunshine in their day

Sitter Profile Image: Andrea C.
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Andrea C.
from
$30
per visit
5 years of experience
Waukegan, IL, 60087

About: Hey there!! I’m a passionate animal lover with a deep dedication to providing the best care for all pets. I believe in making each pet feel cared for and comfortable, adapting to their unique needs. I previously cared for an Australian Shepherd (little guy in the costume) for over two years, so I understand the bond and love that is necessary to each fur baby. Your pet’s happiness and well-being are my top priorities, and I’d be honored to give them all the love and attention they deserve! I am currently working from home and am working on my nursing degree. I am able to accept all time slots of early mornings and afternoons during the week and weekends! I currently do not have any pets here in my apartment but if needed, I have lots of living room space for running and stretching. As well as lots of time to hang out outside in our nearby parks and small trails around the apartment complex. :)

Sitter Profile Image: Marissa C.
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Marissa C.
from
$28
per visit
3 years of experience
Pleasant Prairie, WI, 53158

About: I’ve always loved animals and have had 4 of my own. For the past two years I worked in a dog grooming salon so I’ve worked professionally with dogs and know how to take care of them pretty well. I’m working a part time job right now so my schedule usually depends one the day. I’m usually free after 4 on the weekdays and free on the weekends it just depends on the day. I have a fenced backyard so they won’t be able to get out and if i’m at a clients home i’ll watch them extra closely.

Sitter Profile Image: Paige A.
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Paige A.
from
$20
per visit
5.0 out of 5 stars
• 1 review
10 years of experience
Kenosha, WI, 53142

“Paige was great with Candy! She was very flexible with our crazy schedule and communicated well!”

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Deana K.
Sitter Profile Image: Aracely D.
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Aracely D.
from
$15
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
2 years of experience
Waukegan, IL, 60085

About: Hi, I'm Chelly! I've always been an animal lover and have had the privilege of loving and caring for so many fur babies at Yuppy Puppy in Lake Bluff for about 2 years! I'm based in the Lake County and North Shore area, but if you're a bit farther out, don't worry, I'm always open to finding the perfect fit. Whether your pup needs a walk, your cat wants a friendly check-in, or you need someone to house sit while you're away, I am ready to help! I love working with animals of all ages and backgrounds, playful puppies, curious kittens, wise seniors, and even pets who need medications or a little extra love. I'm here to attend to your pets and your needs as an owner! :) I have a dog of my own, a sweet doodle named Bambi, and she ignites my love for dogs every single day. I know your pet is truly family and I promise to care for them as if they were my own, showering them with love and sending you plenty of photos so you always know how they're doing. 🐾 ♡ I have a flexible afternoon schedule to fit all pet parent needs! I am currently a student in online school, and work as an RBT from 8:15 - 3:15. I'm always willing to try and accommodate as much as possible, so don't be afraid to ask. :) When I’m house sitting, my goal is for your pet to feel like they’re hanging out with a friend, not just someone filling in. I pay close attention to the little rituals, favorite toys, bedtime snuggles, and those everyday quirks that mean so much to your pet. I’ll do my best to keep their world steady and familiar, so they can truly relax while you’re away. Your home will be treated with respect, and your furry companion will get plenty of love until you return. I always pay attention to detail, making sure doors are secure, gates are latched, and your pet can explore safely. Whether we’re out for a sunny walk or just lounging at home, I’m watching for every tail wag, ear perk, or sign that your pet needs something. With experience caring for both mellow seniors and energetic pups, I’m flexible and patient, ready to adapt to whatever makes your pet happiest. Your pet will always be treated like family! :)

Sitter Profile Image: Payton A.
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Payton A.
from
$17
per visit
10 years of experience
Kenosha, WI, 53142

About: I’ve taken care of dogs, pigs, chickens, and cats. My whole entire life I have had to take care of special needs animals as well. During the week, I am available anytime during the week I’m available all day long! I am available on the weekends as well! Let me be your safe space for animal sitting! I will be able to provide to your animals all day long on the weekends, afternoons on the weekdays, ensuring that they are fed watered taken out walked and cleaned if need be

Sitter Profile Image: Samantha V.
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Samantha V.
from
$30
per visit
28 years of experience
Kenosha, WI, 53140

About: I’ve had and cared for dogs my whole life. I currently have four about 50lb dogs. (A Silver lab, pit bull/boxer, chocolate lab/pointer, and a vizla/pit bull/lab mix). Two that were rescues. My mom worked in a vet clinic when I was a child, and I grew up to be a vet assistant at a clinic myself. I know what to do in emergency situations, and remain calm. I am a very loyal and responsible person. I am also a very loving and caring individual. I love every shape, size, and type of dog. They are all unique and want to be loved in each individual way. I would love to be the person to bring your dog happiness by playing with them, walking them, and giving them what they need.

Sitter Profile Image: Valeria A.
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Valeria A.
from
$45
per visit
5.0 out of 5 stars
• 14 reviews
2 repeat clients
11 years of experience
Wadsworth, IL, 60083

About: Hi! I'm Valeria, a freelance designer and proud parent of two mid-sized adopted dogs, aged 6 and 7 years. I adore caring for animals and find true happiness in their company. My dogs bring so many wonderful moments to my life, and I deeply understand the importance of giving them the attention and care they need. I'm also passionate about all sizes of dogs and cats. In addition, my hobby is horse riding, so I'm learning how to take care of horses as well. I’m currently working part time so I will be happy to take care about your wonderful pets! It’s a pleasure for me to spend time with animals! I will focus on the individual and distinct needs of each animal. I firmly believe that every pet is unique and deserves personalized care. By adhering to the specific requirements set by owners, I aim to ensure that each pet feels exceptional and cared for, making their experience wonderful

Sitter Profile Image: Michelle Z.
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Michelle Z.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 49 reviews
17 repeat clients
3 years of experience
Sturtevant, WI, 53177

“Michelle has been excellent ! We are so fortunate our Mabel had such awesome care and attention . We felt very comfortable having Michelle in our home and spending time with our best girl ! I highly recommend Michelle to anyone who loves their pet(s) and wants the security of knowing they are loved and cared for 1,000% of the time . I was nervous to use Rover as I am first time user . Michelle made it so easy and comfortable .”

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Eileen F. G.
Sitter Profile Image: Bob and Francine A.
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Bob and Francine A.
from
$36
per visit
4.9 out of 5 stars
• 45 reviews
29 repeat clients
30 years of experience
Gurnee, IL, 60031

About: We are animal lovers who would love to have your dog or cat stay overnight, for a weekend or a week! We currently have three dogs and 4 cats. We also have various foster dogs at any given time. Some are a little shy but they are all socialized and well behaved. We prefer to take the dogs on a walk when meeting but the interaction is entirely dependent on you and your dogs comfort level since you know your best friend best. We have a fenced in backyard perfect for running and playing. We try to walk the dogs several times a week. Although we have a crate, we don't use it unless your dog is not house broken or if your furry friend needs some alone time while eating. Come on by for a "bark, sniff and greet". We have plenty of doggie beds and cat perches so that your furry friend will feel right at home. We treat all dogs like family so you have no worries while on vacation! I work from home part time so I am available to take care of your furry friends. My personal dogs love other dogs and are very eager to greet new dogs. I have a fenced in yard that backs up to a creek. My neighbors on one side have chickens and on the other side the neighbor has a dog.

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The median cost per visit for pet sitting in Winthrop Harbor is $20

Pet parents share their Rover experiences - Winthrop Harbor

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5.0 out of 5 stars

Absolutely wonderful with my boys while I was out of town. My nervous one was super comfortable with her, which is always huge for me. Lots of notes and pictures to keep me updated. Will definitely book again.

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Erin M.
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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Why Choose Rover?

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    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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

How to book pet sitting

  1. 1. Search

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  2. 2. Meet In Person

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Popular requests for pet sitting - Winthrop Harbor

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Sitters in Winthrop Harbor average 7
repeat pet sitting clients

FAQs for Pet Sitting - Winthrop Harbor

Frequently asked questions about Rover

The average cost of Pet Sitting in Winthrop Harbor on Rover is $17 per visit as of October 2026. Most bookings cost between $17 and $31 per visit. 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 3,930 sitters on Rover offering Pet Sitting across Winthrop Harbor. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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 .

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 , which provides up to 25,000 in eligible veterinary care reimbursement.

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

  • 88% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 94% 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.

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 .

sitters on Rover set their own , 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.

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