Pet Sitting Winthrop Harbor

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Over 46
pet parents in Winthrop Harbor have booked pet sitting

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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: Hannah M.
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Hannah M.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Pleasant Prairie, WI, 53158

About: I have experience working with all kinds of animals, as I grew up on a rescue farm. We rescued dogs of all ages and cats from multiple litters! I’m currently working full-time in a hospital, but I am looking for some extra work outside of it on the weekends and some weekdays. This is a great activity to decompress with animals and make extra money! I will ensure that I keep the clients home safe and secure when leaving. I will respect boundaries and ensure that I go and do my job, taking care and playing with your pets!

Sitter Profile Image: Caitlin C.
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Caitlin C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
252 reviews
65 repeat clients
15 years of experience
Kenosha, WI, 53142

Caitlin was great. She did everything we needed and sent plenty of pictures. She brought in our mail and left a sweet Christmas card! Will def book again.

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Kasey H.
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: Kim K.
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Kim K.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
49 reviews
12 repeat clients
40 years of experience
Kenosha, WI, 53143

Kim took wonderful care of our cat and dog. Neither of them is quick to warm up to new people, but she was communicative, prompt, and patient. It gave us so much peace of mind while we were away. We’re really grateful and would happily recommend her to anyone looking for great pet care.

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Taylor and Eileen
Sitter Profile Image: Robert P.
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Robert P.
from
$12
per visit
14 years of experience
Zion, IL, 60099

About: I’ve worked hands-on with animals for over 12 years through shelters, rescue organizations, fostering, and TNR work. I’ve cared for everything from neonatal kittens to senior and special-needs animals, including medication administration and post-op recovery care. I’m calm, reliable, and experienced with animals that may be nervous, shy, energetic, or need extra patience. My goal is always to make pets feel safe, comfortable, and cared for while their owners are away. With my current work schedule, I’m available early mornings (5–6 AM) before work, again around noon, and throughout the evening. I make pets a top priority and can also provide late-evening check-ins to help pets settle in comfortably for the night. Based on your pet’s normal routine and comfort level, I can accommodate leash walks, supervised backyard time, or longer walks and exercise as needed.

Sitter Profile Image: Cynthia G.
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Cynthia G.
from
$15
per visit
5.0 out of 5 stars
1 review
1 year of experience
Pleasant Prairie, WI, 53158

About: Whether your pup enjoys long walks, playtime, belly rubs, or simply relaxing with someone nearby, I’ll make sure they feel comfortable, safe, and loved while you’re away. My goal is to provide a calm, loving environment where your pet receives plenty of attention, affection, and exercise. I am retired so have plenty of time to play with and walk your fur babies as much as needed. I can play with your dog in our fenced in yard or walk them on the Bike Trail, which is just a block away from our home. I’ll tailor my care to each dog’s individual personality and routine. I know how important consistency is, so I’ll follow your feeding schedule, medication instructions, exercise needs, and any special requests. I like to text or email regular photo updates and messages so you can relax knowing they’re having a great time, communication is just as important as great pet care.

Sitter Profile Image: Sunshine L.
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Sunshine L.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
99 reviews
32 repeat clients
46 years of experience
Kenosha, WI, 53143

Sunshine and her children took wonderful care of Leila. I enjoyed all the pictures she provided us of playtime and cuddle time. Sunshine was dependable and communicated with us every visit. She allowed us to have a stress free vacation. I would definitely recommend her for your fur baby. Thank Sunshine!!!!

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Tonya G.
Sitter Profile Image: Elizabeth P.
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Elizabeth P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
1 year of experience
Wadsworth, IL, 60083

Liz took the best care of our two dogs. One of our dogs is a bit nervous and she was great about the needs of each dog with different personalities. It was our first time to be away during the night without the dogs and they were perfectly fine with Liz making several stops throughout the day. We will definitely ask for Liz to care for our dogs in the future. She’s very good about communicating and prompt with all the requested visits. I highly recommend Liz. She is so nice and professional.

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Joanne B.
Sitter Profile Image: Edge C.
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Edge C.
from
$10
per visit
1 year of experience
Zion, IL, 60099

About: Hi! I’ve cared for pets for years through feeding, walking, playtime, and providing companionship. I understand that every pet has unique needs, and I strive to make them feel safe, loved, and comfortable while their owners are away. I currently work part-time, which allows me to maintain a flexible schedule and dedicate quality time to the pets in my care. I strive to provide reliable, attentive care through walks, playtime, feeding, and plenty of companionship. Your pet’s safety and comfort are my top priorities. I have a secure, fenced yard where dogs can play and exercise safely. I also have young children in the home who have been taught to be gentle and respectful around animals, helping create a loving, family-friendly environment for pets in my care.

Sitter Profile Image: Christine S.
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Christine S.
Star Sitter
from
$27
per visit
5.0 out of 5 stars
8 reviews
5 repeat clients
30 years of experience
Gurnee, IL, 60031

Extremely happy with Christine. This is the first time I've had a drop in visit for my pets in 10 years. Christine reassured me and even came to visit my fur babies before. She brought an ease and I felt complete trust that they were in good hands. I was given many updates every visit and pictures. She was thoughtful and always on time. My pets were very comfortable with her. Which made my trip less stressful. I would definitely recommend Christine and I will happily recommend her and have her back again in the future.

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Rosie A.
Sitter Profile Image: Marcelina B.
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Marcelina B.
from
$19
per visit
5.0 out of 5 stars
27 reviews
11 repeat clients
10 years of experience
Kenosha, WI, 53142

Marcelina provided the best care to my babies! She is super friendly, responsive and provided regular updates for each visit. I would highly recommend her to anyone!

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Sarah N.
Sitter Profile Image: Emily F.
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Emily F.
from
$17
per visit
12 years of experience
Kenosha, WI, 53143

About: I’ve had pets (dogs, cats, fishes, a turtle) my whole life and genuinely love caring for animals. I currently attend training classes with my own dog, so I’m always learning more about positive training and animal care. I’m also a vegetarian and have a strong love and respect for animals. As a nighttime caregiver and daytime special educator, I’m patient, responsible, attentive, and comfortable caring for others with different needs. I’d love the opportunity to give your pets the same care, attention, and love I give my own! I currently work part time and have a very flexible schedule! I’m available weekdays and weekends within a wide variety of times throughout the day and I’m always willing to work around your schedule. I’ve had dogs and cats my entire life and understand how important it is to make pets feel safe and comfortable. I’ll follow your instructions carefully, provide plenty of attention and supervision, and make sure your pet gets the care, exercise, and affection they need.

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

Amazing human and absolutely fantastic service. Jessika went above and beyond for my fur babies and I would rehire her immediately with no hesitation at all.

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Kris B.
Sitter Profile Image: Victoria-Anna K.
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Victoria-Anna K.
from
$15
per visit
5.0 out of 5 stars
1 review
1 repeat client
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: Celeste G.
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Celeste G.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
13 years of experience
Wadsworth, IL, 60083

About: I’ve cared for a variety of pets of all ages, from energetic puppies to independent cats. I am comfortable caring for senior pets, ensuring they get the proper attention and care they need- as long as instructions can be provided to maintain routines and medical needs. I treat every pet as if they were my own, providing gentle care, companionship, and a safe environment. Wether it’s keeping up with a puppy, a shy cat, or providing extra comfort for an aging pet, I would be honored to be trusted with your furry family members. I currently am a full time Software Engineering student at Loyola University! Currently, most of my coursework is online other than Tuesdays and Thursdays. This limits my availability on those days for additional pet care. My flexible online schedule allows me to dedicate plenty of time to care for pets throughout the week, ensuring they receive attention and care they deserve. I can easily accommodate feeding schedules, playtimes, and check-ins, making pet care a natural and enjoyable part of my routine. I provide a safe, comfortable, and pet-friendly environment for all animals in my care. My home has a large yard with fencing where I can comfortably walk one’s pet outdoors while remaining safe. I have two cats and one dog in the home, so I do carefully manage introductions and limit interactions if needed to ensure all pets are comfortable. For dogs, I can crate or pen if needed, providing them with personal space, or allow them to roam safely on a leash outside while ensuring they are well cared for inside. For cats, I prioritize an stress-free environment, providing personal space and ensuring quiet areas to retreat to. I understand feline body languages and can understand shy, playful, or independent cats to ensure their comfort.

Sitter Profile Image: Teri T.
Verified Enhanced Background Check
Teri T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
50 reviews
9 repeat clients
40 years of experience
Waukegan, IL, 60087

Teri was an excellent catsitter and really helped put our minds at ease that our cat would be well cared for while we were away. Teri was very commutative and flexible and we appreciated the detailed daily updates about our cat. We would definitely recommended and rebook with her!

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Beth F.
Sitter Profile Image: Alissa K.
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Alissa K.
from
$20
per visit
10 years of experience
Kenosha, WI, 53142

About: I've been dog-sitting my friends' & neighbors' dogs for years now. Everything from Shih Tzus to Labs to Collies and Pit Bulls, I do well with all types of dogs! I love taking dogs for walks and playing fetch! (Also, I love cats! (I'm a Cat Mom of 4)). I'm currently working part-time, so I have plenty of time to take care of your pet(s)! My weekly availability varies, but I keep my calendar up-to-date. I respond promptly to requests, so feel free to reach out and ask! I am always respectful of my clients' homes & make sure I take the dogs out frequently to use the bathroom & for walks/play, that litter boxes are cleaned, & that there is always fresh water/food given.

Sitter Profile Image: Faith Q.
Verified Enhanced Background Check
Faith Q.
Star Sitter
from
$23
per visit
4.9 out of 5 stars
50 reviews
36 repeat clients
20 years of experience
Gurnee, IL, 60031

This was our first time with a dog sitter , faith was great with the drop ins and we are so happy with are experience with her definitely would book again !!

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Olivia H.
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: Kelsea D.
Verified Background Check
Kelsea D.
from
$16
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
9 years of experience
Waukegan, IL, 60087

About: Hi Kelsea here, I have some experience, about 2 1/2 year training dogs. Having a fur babe/babies is the best thing anyone could have, they can be sometimes better than humans. Love being outside and playing with my puppy and yours too, just see there happy faces makes my day great. My apartment where am stating currently dosent allows any aggressive breeds you should be able to see the picture of what am not allowed to have. But, am hoping to have a house to where i be able to have any breed. Currently I am working at Rally’s. But,I am very flexible to you and your dog needs. Also hoping to go back to college so I can get my degree in medical office, while there am hoping to learn more about training animals too. In conclusion, I hope that you and your fur babe/babies will choose to come and have a awesome experience. Have a great day!!!

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

Cat parents share their Rover experiences - Winthrop Harbor

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5.0 out of 5 stars

Abby did a great job checking in for our two cats during a long trip. Both cats were very happy and healthy during that time and we were so pleased to see them relaxed when we got home from our trip. It really made us feel good to know that our babies were the best of care! Highly recommend Abby!

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Lisa T.
Drop-In Visits
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Sitters in Winthrop Harbor average 6
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FAQs for Drop-In Visits - Winthrop Harbor

Frequently asked questions about Rover

The average cost for Pet Sitting in Winthrop Harbor on Rover is $18.32 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 Pet 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 Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 4,032 sitters on Rover offering Pet Sitting across Winthrop Harbor. 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 Winthrop Harbor 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.

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 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.

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

  • 92% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 96% 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 short introductory meeting between you, your pet, 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.

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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