Dog Sitting Winthrop Harbor

“Declan clearly dedicates his time making sure our dog is mentally and physically engaged during his visits, which is not an easy feat with an energized 6mo lab! We are very grateful to have an enthusiastic and experienced handler like Declan around.”

Brittney L.

About: I provide loving, attentive, and reliable care for dogs of all breeds and sizes, ensuring they feel safe, comfortable, and happy while their owners are away. I follow each dog's routine closely, including feeding, walks, exercise, playtime, and companionship, while giving them the patience and attention they deserve. I take pride in building trust with both pets and their owners through clear communication, dependability, and a genuine passion for animal care. Pet care fits naturally into my daily and weekly routine because I enjoy spending time with animals and have a flexible schedule that allows me to provide consistent, attentive care. I am able to accommodate feeding schedules, playtime, walks, litter box maintenance, and any special care needs. Whether it's a daily visit or extended care while owners are away, I make pet care a priority and ensure each pet receives the attention, companionship, and reliability they deserve. I care for pets by following their normal routines as closely as possible to help them feel comfortable and secure. In my client's home, I provide feeding, fresh water, litter box cleaning, playtime, companionship, and any other care instructions provided by the owner. I pay close attention to each pet's personality and needs, ensuring they receive plenty of affection, exercise, and attention while maintaining a safe and clean environment. I also keep owners updated with messages and photos so they can have peace of mind knowing their pets are happy and well cared for. My goal is to make every pet feel loved, comfortable, and stress-free while their family is away.

About: I have 16 years of experience caring for others' animals. I worked for multiple horse farms until graduating college and all types of animals. Horses, donkeys, cows, big dogs, little dogs, pigs, bunnies, birds, I've taken care of them all! The bigger the animal the more comfortable I am with them. I work full time but I have a hybrid schedule that I make. I travel all over Cook/Kenosha/McHenry/Lake/Dupage Counties so if you're in that area I can tailor my schedule to spend more time in that area the week you need to accommodate your pets needs with daily walks or overnights. I treat all pets like they are my own. I take the time to get to know what they like so they warm up to me. Their favorite napping spots or where they like to be scratched. I want them to feel as comfortable as they can be while their owner is not around. I try to be the fun aunt that comes to visit so they don't notice mom and dad are gone.

About: I have one dog and one cat that tend to stay upstairs. I absolutely love animals, So I hope to have my own little hobby farm one day. If your pet is in my home, please know they’ll always feel loved, safe and most likely tired out from all out walks. I believe humans and animals benefit from exercise which helps with behavior, same for humans. So bring your pup to me, and they’ll be tired for you:) Also, I have a special place in my heart for special-needs animals that need a little extra love and patience. I have been doing dog-watching for the past four years, in addition to working part-time for 10 years. I work at a school right down the road, which is perfect for dog watching. I leave at 7am, and I’m back by 11am each day. I do boarding, play dates, pickups, drop-ins, and trips to the dog park. I have a fenced-in yard, so your dog may play, run, or simply get some fresh air. I spend my time walking dogs, feeding them, playing, cuddling, kisses, relaxing on the porch and constantly opening and closing the door so they can go outside. Ha! It’s my life, and I truly love it.

“Nick is awesome, cares so well for the cats and is fully recommend him.”

David M.

“Monica is an exceptional pet sitter! Provides prompt responses, real time pet updates with pictures and my big guy Ripley is happy and safe when she provides pet care services. I am able to have piece of mind that my dog is well cared for when Im not in town, and also able to have communication with her. I just finished my second booking with Monica and will continue to book with her. Highly recommended!”

Miller H.

About: I’ve grown up with pets my whole life and have done sitting on the side for family and friends. I have raised my dogs from puppies to now they are 15 and 10 I also got a kitten about a year ago and she’s been enjoying the ride ever since! I am currently in college. I am planning on getting another part time job so I will be sure to communicate with my clients the schedule for that. I take care of my own pets everyday and would love to add yours too. I have grown up with animals my whole life so their routine is my routine. I believe that we owe it to our pets to make sure their needs are met and that they are happy.

About: I’ve spent a majority of my life around animals. Growing up, we had a variety in the house (dogs, cats, fish, squirrels). I’ve learned that being calm, loving, and patient is the key to dealing with any pet. Like people, pets have their own quirks and personalities that is an absolute joy to learn about! I currently assist my sister with her two boys. Now that they are both in school, my schedule is much more open. I help get them to school early in the morning, and help pick them up in the afternoon. I have no problem helping with specialty pet needs and care, whether that be crating, medications, or assisted devices. Your pets are in great hands :)

About: I'm Julie (Jules), a graphic designer and creative director. I own a design and branding company in the Chicago/Milwaukee area that services clients locally, nationally and globally. I love all creative pursuits, including writing music for piano and singing. I've always loved all dogs, especially larger breeds (though the smaller pups are super cute and sweet and steal my heart equally!). My pup, Bella, a black lab mix, was a very kind, sweet and gentle dog. She passed in 2016 at age 14, having had a very nice life. I would love to help other fur babies who need caregiving while their humans are away or need a daily walk or check-in. I'm at home working during the week and have access to a wonderful backyard, an amazing neighborhood, and parks nearby. I love all outdoor activities, especially hiking and swimming. Would love to take your pups to the beach or on any sized walk they desire!! :) I offer these services because I love dogs, not to make a living. It's a great win/win to have a sweet fur baby around from time to time. Yes, it's nice to have some extra cash to work on the house, but my primary career more than covers my income needs. I share this info so you can be sure no other dogs will share your pup's time with me.* I keep to a strict policy of one-on-one care and up to two dogs from the same family... if you have more than two, please reach out, and I may be able to make exceptions. My rates reflect this customized care and focus for your sweet puppers! *In mid-2024, I started pairing up dogs that requested having another pup present from a different family. Please let me know if you are open to having a playmate for your pup. If you prefer no other dogs in the home while yours is here with me, I strictly adhere to your preferences and take this quite seriously. I specialize in customized care for dogs with behavioral issues such as not getting along with other dogs. Since my dog passed in 2016, I have been able to devote all my time to your pup when they're in my care. They will be carefully cared for and pampered, with every need catered to. The only thing I won't abide is a pup who isn't house-trained. If your dog/pup has never been left with a sitter before and you'd like to ensure they're a great house guest, I do suggest booking a 1-2 night stay much in advance of your trip so we can see if your pup has any specific issues to call out, and if I'm a good fit for them/you. I have found this to be of great benefit to you and me! I charge a cleaning fee IF your pup has "surprise" issues with incontinence, as this behavior can happen; however, I don't take on dogs with this issue unless we have a solution, like a doggy diaper or pee pads (for puppies). Severe separation anxiety can also be challenging, as my own pup had this issue. If there are situations such as this, I ask that you bring a crate, and the pup must be trained and be OK to be in their crate as needed. If no issues like these exist, they need to have their own bed or spot where they like to sleep. I don't allow dogs to sleep upstairs with me. Snuggling up on the sofa with a couple of pups is one of my favorite things to do. I know most dogs like a comfy bed. As noted above, please bring a fresh bed for your pet, either a cleaned dog bed from home or a new one. I have blankets for the floor and a lovely sofa that I cover with a blanket for the occasional daytime snooze. If you have an elderly dog, I know just what to do to provide the best care. As my dog Bella aged, I learned how to adapt every year. Listening to your dog and providing the best care is my priority. I realized that leaving an ailing or elderly pup in another person's care can be stressful. I would treat your dog like my own and hope to put your mind at rest. I welcome all questions as part of our meet + greet. I only sit for dogs I know or can meet during our meet + greet (unless out-of-town circumstances or timing prevail). I can sit at the last minute only for pups I've sat for previously or know well. If you are traveling from out of town and cannot sync up for a meet + greet, please reach out to discuss your situation. As far as breeds go, I have experience with an extensive range of breeds—larger breeds with special needs like an elevated dog water/food bowl due to how they process food or other breeds that are great with humans and not so wonderful with other dog breeds. I've had great results with training. I have experience with smaller breeds as well. As mentioned, I only sit for house-trained and well-behaved dogs in the home. I book up early... sometimes six months before a planned trip. Please plan ahead to secure your desired dates. I look forward to meeting your amazing pups soon!! Jules I'm home most of the time. I work days and some evenings but make my own schedule. I'm available as needed for all types of customized care. I have a lovely yard for dog play. I would love the same situation if I were dog-sitting in your home. My home is also in a very safe Hales Corners neighborhood. It has a low volume of car traffic and is very quiet.

About: I have numerous years of experience training and babysitting dogs and would love to be your furry friend’s new best friend. I am available for walks, drop in visits, or overnight care. I am new to Rover so please reach out for references! I am a student and working part-time so I will have plenty of time to hang out with your furry friend. I am available for 4-6 hours each day, times varying. I will let your pets out for a quick potty break or a long walk, whichever you prefer. I am comfortable hanging out and providing company to your pet as well as feeding and watering.

“Tania was available super last minute for us and took great care of our dogs! She’s communicative, sends photos and videos, and takes time to play with our dogs. They love her and so do we!”

Elizabeth D.

About: I’ve been a house sitter and dog walker for other people for years, while also taking care of family rescues also! Puppies and kitties of all ages and sizes, from Great Danes to Bichon! I’m currently studying so some fur friends to keep me company are very welcome! My days are very busy, so I’m mostly available on night sits, otherwise drop in sits are good! I’m very attentive and caring, good at cleaning up after the pups and cleaning the house. Walking them and very good about handling strong dogs on walks, never getting angry at them.

About: Hi! I’d love to care for your pet. I grew up in the countryside surrounded by animals, with a veterinarian dad who taught me to love and care for them from a young age. I’m gentle, empathetic, and connect easily with pets – from playful puppies to shy cats. I take my responsibilities seriously and treat every pet like my own. I’d love to meet you and your furry friend! ☺️🐈🐕‍🦺🦴🐾 It fits perfectly, I work part time. I have a flexible work schedule. There will be no problems with accommodation. I manage my time very well. I have an apartment suitable for dogs. There is a lovely dog ​​park next to the house where we can have a great time with your dog.

About: Caring for animals is my passion! With over 20 years experience! Grew up caring & loving for dogs and animals of all sizes! Have rescued over 9 animals of my own and helped train over 20 dogs. Love playing with other dogs of all breeds and playing fetch until the sun goes down! Have experience with cats, dogs, and small animals. CPR/First Aid Certified. Have been a chef my whole life as well so love cooking delicious food for all of my four legged friends. Also Studied massage therapy so I love giving therapeutic rubs to all my furry friends! Animals are my love language. I know how special it is to let someone else spend time with your four legged family members. It would be my honor to care for them while you are not able. I work from home so your animals will have my full attention! I have a passion for caring for animals like they are my family! I have a fully fenced in yard with toms of toys a fdog pool and a full house with a finished basement! With a great private subdivision to walk!

About: Experienced dog lover with over 20 years caring for pups of all sizes. I’ve raised Huskies and German Shepherds myself and have happily looked after many other breeds. Reliable, patient, and passionate about keeping your dog happy, safe, and well-exercised while you’re away! I have open availability and flexibility during the week to fit your scheduling needs. If you’re ever in need of a last-minute sitter or someone long-term, I’m your guy. I provide attentive, personalized care tailored to each pet’s needs and personality. In your home, I follow your exact routines, feeding schedules, and instructions while giving plenty of love, playtime, exercise, and affection. I’m very patient with shy, energetic, or senior pets alike. If I’m caring for your pet in my home, they’ll enjoy a safe, calm environment with regular walks (for dogs), interactive play, and constant supervision. With over 20 years of hands-on experience raising Huskies, German Shepherds, and caring for cats and dogs of all sizes, I prioritize their comfort, safety, and happiness as if they were my own

“Jeremy was an amazing cat sitter! Both my cats were immediately comfortable and really grew to like Jeremy’s daily visits and play time. Super responsive and always sending lots of pics for me to check in on- it’s was such a relief to have them in Jeremy’s care. Highly recommend!!!”

John L.

“Our cats love Travis and we always feel more comfortable knowing he is spending time with them. Travis has a good attention to detail and clearly prioritizes our boys needs. He's also secretly a professional cat photographer or something, we always look forward to his check in photos!”

George F.

About: I have taken care of my dog for 15+ years until he passed away recently and look forward to taking care of your dog with the same car. I work full time 9am to 5pm Monday through Friday but I am available on weekends or nights to take care of your dog. :) I am Offering dog walking services and look forward to meeting your dog and providing proper care. Excited to meet your dog and go for walks

About: It all started out with my love for animals when I was younger. I started out my career in grooming than transferred over to a veterinarian assistant and became a veterinarian technician. I have over 8+ years experience with dogs and cats in the professional setting. I also have two dogs and one cat of my own that I love dearly. I currently got laid off my day job so I’ll have plenty of time to hang out,play,walk, give treats etc. Thank you for reading my profile. I won’t be offering in my home services due to my animals. When it comes to your pets I will play, walk, feed, kennel ect. Per your instructions

About: Hi Friend, I am Johnathan and Im excited to meet you and your fur baby. I live and mostly service the Chicago area but I'm always willing to travel and discover the surrounding areas. I grew up around dogs and I'm sure your pup will warm up quickly to me. I’ve cared for dogs from Chicago to California, of all kinds, sizes and temperaments - even the feline kind. Send me your shy ones and your energy balls, l've had them all and they all love me. Outside for caring for pups I'm an actor who loves video and board games, a tasty lemon pastry and adventures! Rain, sun or shine - give me a ring and I'll be there! My schedule is extremely flexible so I’m always ready to care for your pup. Rain, sun or snow. I work in collaboration with one of Chicago’s favorite companies so If im not avaible i have a great rec for you and your pup I always leave the home in the exact way I found it and sometimes I make sure to give everything a nice cleaning depending on the length of the stay. I try to follow the routine of the client so the pup feels comfortable If the pup is use to being home alone on most days. The I’ll usually cuddle up with the pup and binge watch Netflix inbetween our walks and our feedings. Whatever the case an adventure will ensue