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

Over 38 pet parents in Winthrop Harbor have booked dog sitting
Winthrop Harbor, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Delaney has been so wonderful to work with! She is very reliable, trustworthy, and flexible! She does a great job communicating with us and she is so good to our dogs! I would highly recommend!”

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.

About: I’ve taken care of dogs since I was young. I still have both of my childhood dogs, Piper and scout. And I’ve helped my friends and family with their pets sense I was about 10! I currently work three days a week, and fortunately I get out of school at 11am everyday so I have plenty of time fluffy friends! I’ve lived my whole life with two fur babies so I’m well trained! I’m always down for a walk or a quick check in to snuggle and take care of your pets!
“Swag was amazingl detailed and kind; followed up; had great information and made sure every detail was taken care of, even washing the cats dishes that were used. Highly recommend!!”


About: I am a single mom in full-time student looking for pet care jobs this summer and fall! I have two little boys with a lot of energy and one five-year-old puppy!! I am home most days all day every day until my school schedule picks up. I’m available for walks pet sitting and tons of little things in between! I have a five year-old female safe Bernard mix who is incredible with other dogs as well as kids. Depending on the care that you need I am available to let the dog out anytime they need. They’re at my house or stop by. Let them out/take them on a walk. I asked that if I do care for your dogs, knowing their good with little children.

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.

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.
About: I absolutely love animals! I have had several dogs throughout my life and I grew up sitting for everything from dogs, to cats to rabbits. Ive had experience caring for dogs & Cats of all ages. I care for them like they are my own by providing love, care, belly rubs, extra cuddles, & exercise while their families are away. I have experience in administering medications when needed and following any dietary requirements as instructed. I have experience in puppy care. Crate training, pad and outdoor potty training and basic commands I work from home so I am available to care for your pet, any time 7 days a week if needed & take multiple walks No pet sitting services will be provided in my own home. I will be happy to provide pet care in the clients home if needed.
About: I grew up with friends referring to my home as a zoo because we had so many pets! Being responsible for family pets at a young age taught me responsibility and how rewarding it is to care for a furry friend. I grew up to work at the medical center of an animal shelter and learned the skills to work with young to senior pets, outgoing and shut down, in n good health and poor. I treat my dog like my kid and will do the same for your pet I'm currently a full time parent to facilitate taking my son to various therapy appointments which allows a lot of flexibility in my schedule. I remember the stress of being at work and worrying about how long my senior dog had been home alone. I would love to help remove that stress from your life. I'm very particular about a sitter following instructions on how to care for my pup to make sure he is as safe and happy as possible. On walks I always ask other person parents to give us space to avoid any unnecessary negative interactions. Any instructions or preferences you have for your pet will be followed to the letter!
About: Hey there! My name is Diamond, & I am what you would call DEDICATED. I will forever go above & beyond for every 4-leg (and 2-leg) individual that I come into contact with! (I have 200+ pictures to prove it! ❤️) I wish to meet & love on every dog & cat in the world….and I believe I am moving into the right direction to do just that ☺️ I am absolutely ecstatic to meet, care for & love on your pup! I’m always available for a meet & greet, (free of charge) you pick the date! I have over 30 years of experience with dogs. I was actually raised with two BEAUTIFUL, massive, well-trained, protective & just outright AMAZING Rottweilers in my home. I’ve always had passionate soft spot for each & every animal in the world, but dogs became my absolute favorite! Growing up, my father was (and still is) a professional dog trainer. I was intrigued while attending many sessions to watch him & learn how he trained most dogs under 1 day! And of course my favorite part was meeting every pup at the end of each class! I’ve found myself looking for the perfect pet sitter for my now deceased Rottweilers, quite a few times. Which eventually led me to become the pet sitter that I myself used to search for! ☺️ I enjoy & cherish all dogs, I assure you no dog is too big or small and all senior or baby pups are welcomed as well ❤️ Most of the time I am available 24 hours a day, and 7 days a week. I make sure to update my calendar daily so that you are seeing accurate availability on your end! I love to go on long walks, slow morning jogs, and enjoy nature with a bike ride through the trails a few blocks away from my home. There’s also a lakefront just a few blocks away! If your doggy wants extra curricular activity, that’s just what they’ll get! Their exercise will fit right into my daily exercise routine ☺️ Going on Adventures with your pups is what I look forward to! Be prepared to come back to a TIRED but relaxed & calm pup. We’ll be sure to send you a TON of pictures so you can see exactly how much fun we had ☺️ We can also have laid back days, cuddles on the couch while I’m intrigued by a good book or watching a good Netflix or Hulu series. Whichever way the the day may go… both you & your pup will be completely satisfied! I do my best to avoid household accidents. Therefore, your dog will go out to relieve themselves every 2 hours. (Every hour can also be accommodated if needed.) From past experiences, I’ve realized that mimicking routines & rules exactly how they are done in the pets home, at my own home alleviates a lot of stress. They may be in a new environment but their routine & schedule will be the same in my home. Example: If your pup is allowed on furniture at home, the pup is allowed on furniture at my home. If your pup is not allowed on furniture at home, your pup is not allowed on furniture in my home. I will ask you specific questions so that I keep the schedule of walking, feeding, & playing very similar if not the exact same, as you would at home. I can also provide positive dog/puppy training with the clicker or with treats. My goal is for you to never stress about needing a pet sitter ever again & for your pup to forget that you’re away ❤️ I am available 24/7. My twins & I go for walks/bike rides daily already, so your pup will fit right in with our daily routine! I also have a HUGE backyard! Your pup will love playing fetch with the freedom to run as far as they want without a care in the world! I care for pets the same way I would care for a toddler (they’re very similar lol!) Making sure all chemicals, irritants, or any hazardous products are all stored somewhere that’s high up and/locked away, feeding on schedule, bathrooms breaks on schedule or when signs of needing to go to bathroom are shown, and plenty of exercise, toys, water & nap time!
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.
About: Greetings! My name is Rachel. I am 32 years old. I am currently a Veterinary Technician at Beach Park Animal Hospital. I have been working there 11 and a half years. Prior, My goal is to extend my experience in animal care to those in need. I am comfortable caring for dogs, cats, and any exotics. I am also experienced in administering any medication for special needs pets. Feel free to contact me with any questions! Just need help administering medications, SQ fluids? Maybe a nail trim or anal gland expression? I can offer these addition services that can be included in the drop-in visit fee. Questions? Please reach out and ask! My experience administering medication I am comfortable administering oral, injectable (subcutaneous, intramuscular, and intravenous), ear, and eye medications. At this time, I do not offer over night services, but am available during the week, and most weekends. I am available most every morning and evening for drop in visits. I do not currently offer in (my) home pet sitting; but will travel to your house to complete your needs. This will provide your pet with additional comfort in being in their own environment.
About: From tiny, to small, to medium, to huge in size...all of them are born with the same loyal heart! If you’re looking for a reliable and trustworthy person who will proudly take out your Doggie/Cat on a roll😃 than I am your match! I’ve always been an animal lover!! I’m so excited to start walking all the 4 legged friends that come across my path. If they have less than 4 that’s absolutely fine too! ♥️💕 NOTICE: I am not available to do mornings on weekdays.. I am able to do late afternoon/evenings from 5 pm and after on Weekdays. I am able to do Fridays from 6 pm and on. Saturday and Sundays are open (anytime) I have a fenced home with my little guy (Yorkie+Maltese Mix 8lbs) to keep your fur baby company I can always keep my pup crated if necessary.
About: I have had animals my whole life, mostly dogs. I recently was able to get my own dog for the first time as an adult. To say I spoil Burt is an understatement. We go on great adventures to the dog park, hikes and out to dog friendly restaurants. I am completely obsessed with all fur babies and will take care of yours like it was mine. Very safety orientated. I am a flight attendant currently working part time, so when I am home... I am home with lots of free time. I have recently reduced my schedule because the skies are not so friendly at the moment. I would like to supplement my income with helping others and their fur babies. I have a smaller condo which might not be condusive for larger dogs, but if they come over here we always get out for walks and dog park time.
About: I have a love for animals, if you're thinking I'm sure everyone says that but for me it's so true. Not only do I love caring for pets. I've even helped my neighborhood with feral cats and getting them the help the deserve. Look up on Facebook Winthrop Harbor Wild Cats! What does that mean for you? I'm passionate about caring for animals means I will love on and treat your special friend just as you would! My work is flexible and mostly at home. I like to go on walks daily which would fit perfectly for any pup looking for exercise! We have a large yard for easy potty breaks. I have two young children that wear out anyone willing to play. We have a medium crate if needed and a full basement with playroom.
The median cost per visit for dog sitting in Winthrop Harbor is $20
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- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- 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.

Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family

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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 July 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 July 2026, there are 4,039 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
- 97% 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.




