Dog Sitting Winthrop Harbor

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

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pet parents in Winthrop Harbor have booked dog 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: Joshua C.
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Joshua C.
from
$38
per visit
4.8 out of 5 stars
19 reviews
9 repeat clients
7 years of experience
Kenosha, WI, 53142

About: Since 2019, I've been committed to the well being of dogs and cats, offering trusted, reliable, and professional care. While my experience may be selective, each client I've served has left glowing reviews, reflecting the quality and dedication I bring to every job. Your pet companion is in good hands with my proven track record of satisfied clients. My current availability for pet services is contingent upon my full time employment, which spans Monday through Friday from 9:00 AM to 5:00 PM, usually. My work is flexible as well. I am able to bring animals to my office. I operate on a hybrid work model, with a predominant presence in the office rather than at home. In my home or at my client's, the pets' safety and happiness are my top priorities. I customize care routines for each furry friend, sticking to their usual schedule for feeding, playtime, and keeping an eye on them. I make sure the environment is safe and comfy, and I'm always up for fun and cuddles to keep them content. I keep the client updated and have a plan in case of any surprises. Basically, I aim to make sure the pets feel right at home, whether they're with me or at their owner's place. I do have a fenced in yard and my own space to keep the pet comfortable.

Sitter Profile Image: Rachel W.
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Rachel W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
8 years of experience
Kenosha, WI, 53142

Rachel was great, accommodated my last minute request and my little guy had a blast with her.

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Andrew F.
Sitter Profile Image: Victoria-Anna K.
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Victoria-Anna K.
from
$15
per visit
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: Danielle W.
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Danielle W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
94 reviews
24 repeat clients
14 years of experience
North Chicago, IL, 60088

Danielle was wonderful taking care of our cats. She took time to know and to give attention to each of them. She is amazing, and we will definitely book with her again 😊

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Vivianne M.
Sitter Profile Image: Nathan C.
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Nathan C.
from
$15
per visit
2 years of experience
Waukegan, IL, 60085

About: Helped out family since I was little taking care of their furry family members. Also have volunteered numerous times over the years at local shelters and animal control. I currently work full time, so my hours may be a little odd. Switching to part time soon, so I will have more hours other than weekends opening up My dog is the center of my universe. Treat her like a member of my family. Make sure she gets plenty of exercise and attention everyday so that no day is boring for her if I can help it.

Sitter Profile Image: Nathyeli S.
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Nathyeli S.
from
$15
per visit
16 years of experience
Waukegan, IL, 60088

About: For the past 16 years, I've had the privilege of caring for the beloved pets of my family and friends. Caring for animals has always been a natural part of my life, and I truly enjoy getting to know each pet's unique personality and needs. My parents have two Xoloitzcuintli (Mexican Hairless) dogs who require plenty of attention, exercise, and interaction. Whenever my parents travel—often for several weeks at a time—I stay in their home to care for them. During that time, I provide multiple daily walks, playtime, mental stimulation, and plenty of affection. I also carefully follow their routine, including administering daily medications and any special care instructions. I also have experience caring for dogs with separation anxiety and understand the importance of patience, consistency, and creating a calm, reassuring environment. Additionally, I cared for a rescue dog with PTSD and, over time, earned their trust to the point where they felt comfortable approaching me for affection. Experiences like these have taught me the value of allowing animals to build trust at their own pace. Cats have been a part of my life for the past 16 years as well. I've cared for cats with a wide range of personalities, from playful kittens and affectionate cuddlers to independent cats and senior companions with special needs. I also volunteered at a local animal shelter, where I helped clean, socialize, play with, and care for the cats to help them feel safe and comfortable while waiting for their forever homes. Whether I'm caring for dogs or cats, my goal is always the same: to provide a safe, loving, and stress-free environment where every pet feels comfortable, cared for, and treated like family. As a full-time student with a flexible schedule, I'm able to accommodate a variety of pet care needs, including daytime visits, evening care, weekends, and many last-minute bookings. My goal is to give you peace of mind knowing your pet will be treated with the same love, patience, and attention I would give my own. I'm currently a full-time sonography student completing my clinical rotations. Before returning to school, I worked in the medical field, most recently at a cancer center, where I developed a strong commitment to providing compassionate, attentive care. Caring for others has always been at the heart of who I am, and that same dedication extends to the animals I care for. For years, I've been the person family, friends, and neighbors rely on to care for their beloved pets. Whether it's walking dogs, checking in on cats, staying overnight, or helping out with last-minute requests, I genuinely enjoy making sure every pet feels safe, loved, and comfortable while their owners are away. Several people encouraged me to join Rover because of how often I already care for their furry family members. I understand that every pet has their own personality, routine, and needs, and I take the time to earn their trust while providing patient, dependable care.

Sitter Profile Image: Veronique S.
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Veronique S.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
28 reviews
6 repeat clients
45 years of experience
WAUKEGAN, IL, 60087

Veronique was wonderful with my two huskies- I am always super concerned when I leave them alone & stress over their care. She was great at keeping me updated, sent me consistent updates, photos and videos. It’s important for me that my dogs connect with their sitter and it seems my two connected very well with Veronique. I’d absolutely recommend her and would totally book future sitting appointments with her. Thank you much for caring for my big boys 🐶 🐶

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Adonay G.
Sitter Profile Image: Aracely D.
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Aracely D.
from
$15
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
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 an extremely flexible schedule to fit all pet parent needs! I am currently a student in online summer school, but am available Monday-Saturday, 6:00 AM - 5:00 PM. I'm always willing to work outside this schedule for the right person, 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: Jennifer C.
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Jennifer C.
from
$17
per visit
3 years of experience
Kenosha, WI, 53143

About: I care for and walk my 70 lb Doberman every day, so I’m very comfortable handling larger dogs and giving them the attention, exercise, and care they need. He’s not just my dog he’s family and I bring that same love and responsibility to every animal I care for. I’m a true animal lover and often pet sit for friends and family while they’re out of town. I’m now excited to extend my services and provide the same dependable, caring experience to other pet parents. I’m available early mornings, and I’m flexible during the day on Mondays and Fridays. On Tuesdays and Wednesdays, I’m available after 4:00 PM, and my evenings are flexible. My dog has full access to my home, and I also have a backyard dog run that spans the perimeter of the yard. I’m flexible and happy to work with your preferences and your pet’s needs.

Sitter Profile Image: Paige A.
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Paige A.
from
$16
per visit
10 years of experience
Kenosha, WI, 53142

About: I am available daily and would be delighted to assist you with walking or caring for your animals. I possess over a decade of pet care experience and hold a background in animal care through the 4-H program. I am passionate about all types of animals, regardless of their size or species! I personally have five furry companions, so I deeply understand the significance they hold for you. I have had the opportunity to observe and care for a diverse range of animals, so if you have any further inquiries about my qualifications or my approach to animal care, please do not hesitate to contact me. Thank you for considering my services for your animals and home. I am eager to assist you with any needs you may have. Currently employed as a chiropractic assistant, I am fortunate to have ample free time during the weekends, as my work schedule does not include Fridays through Sunday. This allows me to fully utilize my time and resources. Additionally, I reside in a spacious house with a large backyard, providing ample space for any animal needs. Furthermore, I have received extensive training in animal care! At your home I can make sure your animals are leashed and properly walked to assure they come back safely every time I visit! I can provide a safe crate technique if need be and companionship before leaving your home!

Sitter Profile Image: Melissa A.
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Melissa A.
from
$20
per visit
20 years of experience
Lindenhurst, IL, 60046

About: I've taken care of dogs my whole life. I know every dog is unique and needs unique care. I want to make sure your dog is treated with care and understanding while you're away! I have experience giving oral medications (both pills and liquids). I currently have an open schedule for summer! Whether you need a dog walk or multiple visits for feedings while you're away, I've got you covered! I want to build a trusting relationship with you and you're pets. For home visits, I will take time to ensure your pet is eating and drinking well, make sure litter boxes and crates are clean, and each pet knows I'm there to make them feel safe and loved. Is you're pet a little shy? No worries! I'll give their privacy after making sure everything is taken care of.

Sitter Profile Image: Danya A.
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Danya A.
from
$35
per visit
5.0 out of 5 stars
26 reviews
10 repeat clients
15 years of experience
Gurnee, IL, 60031

Danya is an amazing sitter for our little Yorkie, Sophie!

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Jerry G.
Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$30
per visit
5.0 out of 5 stars
6 reviews
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: Grace D.
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Grace D.
from
$14
per visit
8 years of experience
Pleasant Prairie, WI, 53158

About: Whether it's time for a pet session or for the zoomies, I love engaging with and getting to know dogs of all types and personalities. I grew up with 2 dogs, a Labradoodle and Beagle for whom I was the primary caretaker. I found great joy in caring for my dogs who had very different personalities, and I learned a lot about how to handle a multi-pet home. I have continued to grow my knowledge in multi-pet home dynamics with the combination of my household and my partner's. We now live happily with 1 cat and 2 dogs. I'm excited to lend a helping hand to other households who are navigating routine with their fur babies. I’m primarily available during the day Tues-Fri as I set my own work schedule. My animals at home are well trained and flexible, so coming to care for yours is a welcome addition to my daily pet care routine. I can occasionally make Mondays and weekends work as needed. I respect every pet owner as the expert on their own pet. I am happy to follow any and all instructions to give your animal the best pet care I can and provide a sense of normalcy and routine for your beloved pets.

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: Samantha W.
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Samantha W.
from
$15
per visit
5.0 out of 5 stars
3 reviews
15 years of experience
Kenosha, WI, 53142

It was great using Sammi for some drop ins. Very reliable and with great communication. The look on my dogs face in pictures, he loved her so much. Looking forward to next time.

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Nicole S.
Sitter Profile Image: Michael H.
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Michael H.
from
$25
per visit
4.6 out of 5 stars
12 reviews
2 repeat clients
20 years of experience
Gurnee, IL, 60031

About: I have over 20 years of caring for animals of all kinds. I am very personal, caring, and will treat your animal with the love they deserve. I have a full time job Monday-Friday. I can walk your dog in the morning and play with them until I leave for work. After work we can play and enjoy what new outside adventures have in store! I have the ability to come to your home if that’s your preference. I am very schedule friendly. I have a big common area and a large park with a dog area. I’m close to a walking path or can just stay in home and play. I am very responsible and have over 20 years of experience. I have two daughters 11,8 that could help as well. They love animals.

Sitter Profile Image: Shelby W.
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Shelby W.
from
$20
per visit
5.0 out of 5 stars
3 reviews
16 years of experience
Kenosha, WI, 53142

About: I’ve been caring for my 17 year old puggle since the 3rd grade. I also have experience with big dogs, as I had a mastiff too! I’m skilled in walks, baths, feeding, and cleanups, and I treat every dog with love, care, and patience. I have experience with many different dog personalities, as my household has fostered dogs for a couple years now too! No matter the size, your pup will feel at home with me! I’m a college student at American University. My class schedule this spring allows me to be available everyday around 3! So I have a flexible schedule allowing me to easily work around your dog’s needs. Whether it’s walks, playtime, or feeding, I’ll make sure your pup gets the love, time, dedication, and care they deserve! I can provide pet care in your home, and depending on your preference, or your pups! If I care for your pet in your home, I’ll stick to your routine and ensure your dog feels comfortable and loved while you're away. I focus on giving lots of attention, play, and care, just like I would for my own dog!

Sitter Profile Image: Brianna V.
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Brianna V.
from
$25
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
3 years of experience
Kenosha, WI, 53143

About: I’m the most patient person when it comes to animals! I have two dogs of my own, Luna my Pug & Chopper my German Shepherd/Husky! I also have a bunny, Twix. I love training them to do new tricks as well as spending every possible second with them whether it’s blowing bubbles for them or cuddling on the couch watching Bluey! I currently do not work so I’m able to watch dogs all day, everyday! I love spending all the time in the world with my animals. I have a fenced yard as well as two super sweet babies to keep your pup company! I also have many toys and activities to do with the dogs.

Sitter Profile Image: Cynthia G.
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Cynthia G.
from
$15
per visit
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.

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

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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
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - Winthrop Harbor

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Sitters in Winthrop Harbor average 7
repeat dog sitting clients

FAQs for Drop-In Visits - Winthrop Harbor

Frequently asked questions about Rover

The average cost for Dog Sitting in Winthrop Harbor on Rover is $17.21 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 3,890 sitters on Rover offering Dog 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.

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 Winthrop Harbor 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 Winthrop Harbor 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 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.

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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