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: Byron G.
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Byron G.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
53 reviews
15 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: 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

Christine is amazing! She is incredibly down-to-earth and a true animal lover. All of my cats came out to greet her, which absolutely never happens on the first visit. She was very responsive, shared lots of great photos, and gave us complete peace of mind while we were away. I highly recommend her!

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Nicole R.
Sitter Profile Image: Amanda M.
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Amanda M.
from
$24
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Kenosha, WI, 53140

About: Worked at a few veterinary hospitals when I was younger. Pet sitting fits my busy mom life and I adore it. Super comfortable with any kind of animal and able to administer medication (even i.v) properly. Also able to recognize any signs of illness or injury in pets while you are out. This is all I do. Giving these pets all of my attention and professionalism is part of my everyday routine. Knowing they are with someone like me will make your day easy. I’ll care for your pets in your own home. This way they are very comfortable in their own environment. Safety and affection are my priorities while they are in my care. Whether it’s a potty break or a walk or even just a check in, they’ll know they are cared for.

Sitter Profile Image: Leah J.
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Leah J.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
6 years of experience

Leah did fantastic with Storm, love getting photos and feedback about our girl when we are gone!

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Hannah T.
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: Isaac N.
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Isaac N.
from
$14
per visit
1 repeat client
10 years of experience
Kenosha, WI, 53140

About: I have cared for dogs and cats of all sizes and temperaments throughout my whole life. I have some experience assisting pets recovering from surgery, that require specific/scheduled care, and those who are physically healthy, but perhaps are just very slow to trust. I am more than happy to meet your pet where they are, and to assist with their needs as much as you are comfortable. Due to seasonal lay-offs at my workplace, I am currently available all throughout the day. I am happy to make trips throughout the day if needed, and/or multiple days throughout the week. I take my dog for regular walks, and am happy to do the same for yours. I also do my best to present a calm and controlled energy with animals, in an attempt to let them grow more comfortable with me at their own pace. I am prepared to be patient if your pets are more shy, and playful if they are more energetic and friendly. Every dog and cat is different, and I do my best to match their energy and respect their boundaries, while ensuring I am also meeting their needs.

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: Danielle W.
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Danielle W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
104 reviews
24 repeat clients
14 years of experience
North Chicago, IL, 60088

Absolutely phenomenal pet sitter. Danielle was fantastic with both cats and very communicative. I would definitely use her again and recommend her to anyone out there!

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William M.
Sitter Profile Image: Kyleigh R.
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Kyleigh R.
from
$16
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
1 year of experience
Kenosha, WI, 53142

My baby had such a good day with Kyleigh! It was my first time leaving him home alone to go to work and her care for him calmed my nerves. She visited him three times and my puppy had no issues, absolutely loved her! She sent me pictures that made my heart melt! Highly recommend Kyleigh!

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Katelyn O.
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: Isabella T.
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Isabella T.
from
$22
per visit
5.0 out of 5 stars
23 reviews
12 repeat clients
18 years of experience
Beach Park, IL, 60099

Isabella was great with our two huskies, she was always there to take care of them, play with them, spend time with them, overall be a great caregiver for my not so little ones. We appreciate Isabella’s work ethic and will absolutely be reaching out in the future when we are in need of a great sitter!

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Adonay G.
Sitter Profile Image: Danya A.
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Danya A.
from
$35
per visit
5.0 out of 5 stars
26 reviews
11 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: 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 a flexible afternoon schedule to fit all pet parent needs! I am currently a student in online school, and work mornings as an RBT until 11:45 AM. 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: Alvaro S.
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Alvaro S.
from
$20
per visit
40 years of experience
Zion, IL, 60099

About: I've been a huge dog lover since I was young owning dogs from dachshund, GSD's, until now where I personally own 2 Boerboels (150-175lb) and a blue nose pitbull. I currently work 3am to 7. Then all day is mine. I coach middle school track and field at 4pm so free to make new furry friends all the time. You can see me walking my Boerboel at lake andrea daily. My yard is fenced and as for transportation I have a suburban and a buick to get the dogs for long afternoon walks. Keeping their minds active is the key.

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: Veronique S.
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Veronique S.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
31 reviews
8 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: Samantha L.
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Samantha L.
from
$20
per visit
20 years of experience
Kenosha, WI, 53140

About: I have worked at shelters and pet stores over the last fifteen years while also working at zoological facilities working with exotics. I have experience with nutrition, grooming, medicine administration (including injections), training, and everything between. My experience puts me at ease around animals and I am confident in my abilities. Whether your puppy needs training, your cat needs a walk around the block, or your senior just wants some company, I am able to provide you and your pets with excellent and professional care.

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: 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: Melissa C.
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Melissa C.
from
$20
per visit
8 years of experience
Winthrop Harbor, IL, 60096

About: Hello! Having recently made Illinois my home, I’m looking forward to meeting local pet families. Over the years, I’ve gained hands-on experience looking after everything from puppies to elderly cats. As a lifelong cat mom myself, I know that pets are family. When you're away, you need someone reliable who respects your home, follows your routines, and provides calm, attentive care so you can have total peace of mind. Now based in Winthrop Harbor, I’d love the chance to meet you and your little ones! 🐾 I have a flexible daily schedule, which allows me to be very responsive to your pets' needs. I'm currently available for drop-in visits throughout the day and can easily accommodate morning, afternoon, or evening routines. Since I specialize in drop-in visits, my priority is making sure your pets feel safe, comfortable, and happy in their own familiar environment while you're away. When I arrive, I handle everything according to your exact routine—whether that means feeding, fresh water, medication administration, litter box scooping, or yard breaks. Just as importantly, I make sure they get quality interaction, playtime, or gentle attention so they aren't lonely. I also respect your home completely, keeping spaces tidy and sending a detailed update with photos after every single visit so you always have peace of mind.

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

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Sitters in Winthrop Harbor average 7
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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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