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

Over 16 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.

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.
“Did an awesome job with all 4 of my pets! Especially with such cold weather during the time she was dropping in on them. Took lots of photos and communicated when necessary! Would book again and highly recommend.”

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.
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.

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.
“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!”


About: My whole life I've grown up with dogs and other animals. I truly care about pets and their well being. I'm pursuing a degree in animal behavior and welfare. I also have watched family pets growing up. I'm currently without a job so I'm available to watch your animal(s) full-time, part-time, or over night if need be. I do live an apartment, but I have plenty of walking space outside, cat toys and trees for anyone with cats. I'm willing to work on a schedule if you need strict walking times or for feeding. I'm willing to train for free using reward-based training techniques and I'm willing to bathe for free if you'd like.
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: 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.
About: I have always had dogs & loved them since I was born. My parents would travel a lot & I would stay and take care of my dogs, I even helped care for and raise 2 litters of puppies! When my siblings, friends, or family friends are out of town, I am always asked to take care of their dogs. I now have an 8 month old puppy of my own, & he is treated like a prince. I have taken him, and my family dog both to training classes, so have experience there. I think I am considered over others to watch people's pets because of how much they know I genuinely care for animals. I ensure their dogs are fed and watered at a timely manner, loved on/cuddled, and happily exercised. I have always had a special bond with all dog breeds and almost all animals, and promise to provide quality care for anyone's dogs/pet :). Pet care naturally fits into my daily/weekly routine, as I have a dog of my own as well. I currently have a job at a bar/restaurant, however I am only working most weekends. This leaves most of my week days quite open. I have used most of this time doing fun things with my own dog, so I thought "why not do fun things with other dogs that need the care?". How do you care for pets in your home and/or your client's home? This will vary depending on which service you offer. Of course caring for pets will vary based on the home, but in my own, I have a fenced in yard with a large amount of space for them to run around in and play. Inside my house I have a cozy living room in which we can hangout in, and a mud room to wipe paws and eat breakfast and dinner and drink water. For another's home, I would abide by their pet rules and use the space they have to maximize my time with their pet/s. Along with this, I am more than willing to take their pets for walks, or even to the dog park if they would like.
“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 🐶 🐶”

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.

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!
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.
“So happy to make a connection with a local who can drop-in to give pee breaks to my three dogs when we're out for a long day. Katie seemed to have the magic touch with my normally anxious male, as he immediately seemed comfortable with her. Will definitely utilize Katie going forward to stop in again!”


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!!!
About: Always had 4+ animals in my household (fish as well!) and always enjoyed taking care of them and going on walks/runs and playing with them. I’m pretty flexible when it comes to scheduling and I’m happy to work around your needs and your pet’s routine. Whether you need someone for a quick drop in, a few days, or even a longer-term stay, I’ll be happy to help! I know how important it is to have someone you trust with your pets, and I’ll treat them like they’re my own while you’re away. 🐶🐾 I’ll do my best to make sure your pets are well taken care of and comfortable in your home. Whether that means playing with them, taking them for walks, feeding them, or even giving them a bath. I’ll treat your pets with the same care and attention I’d want for my own.
The median cost per visit for dog sitting in Winthrop Harbor is $20
Book with peace of mind
- 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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Popular requests for dog sitting - Winthrop Harbor
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winthrop Harbor average 7 repeat dog sitting clients
FAQs for Dog Sitting - Winthrop Harbor
Frequently asked questions about Rover
The average cost for Dog Sitting in Winthrop Harbor on Rover is $16.65 per visit (as of September 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 September 2026, there are 3,845 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
- 95% 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.


