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

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Top rated Winfield dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I grew up in a big family , we always had pets from dogs-hamsters! And we took care as if they were part of the family . I am compassionate, and I would love your animals and care for them and treat them with kindness as if they were family. As a mom of 5 older kids, I’ve gotten really good at balancing routines and staying organized. Now that they’re more independent, I have lots of free time in my day to dedicate to caring for pets, giving them attention, exercise, and a reliable schedule. I did have 3 cats and 1 dog at one time before. They still are part of the family they live with family members and I visit them time to time and they come to my house as well. I love walking dogs and taking care of animals that are only comfortable in your home. I am a trust worthy person when it comes to someone trusting me in their home. Clients should know that their home and their pet are well taken care of and respected.
“Leila was a big help. I booked her for last minute for multiple hours, and she didn’t bat an eye. She just asked where, when and what do you need from me? (In a good way). She completely exceeded expectations and I hope she is available to watch him again in the future!”

“Excellent and good natured! One of my pups wasn’t very nice, and I gave my apologies. This engagement was sort of an emergency and I truly appreciate Donna agreeing to take on this assignment on just a one day notice!”

“Mollie was so good with our boys! She gave great notes and sent plenty of pics. She even added a personal touch of taking Polaroids of them for us! Definitely would recommend her!”

About: I’m a lifelong dog lover and experienced pet caregiver. Sometimes I think dogs like me better than humans do 😂😂. I have the time, patience, and passion to care for your pup as if they were my own. We share our home with a sweet, rescued pitbull who was formerly a bait dog. She’s now thriving with love, patience, and a gentle routine. I also previously owned a cavapoo, so I understand the unique needs of both large and small dogs—from high-energy playtime to cozy cuddles. Lots of cuddles and scritches. I’m a teacher in my 16th year of teaching elementary school music, and I’m looking to make some extra cash for my upcoming wedding and to fill my time over summer breaks. Couldn’t think of a better way than spending time with animals!! We have a SUPER SWEET pitbull and a very dog-like cat and both are very attached to me! I feed and groom both animals, walk the dog, play with them, tend to their bathroom needs, give them lots of scritches and luvins! They sleep with me and are at my side wherever I go, always following me around the house (but never the other people in our household! :).
“Sarah did a fantastic job with my two cats. We did 30 minute drop in visits and she was on-time and made sure to take the time to not just check food and water but to give the cats some playtime and attention. One of my cats required extra care and she handled that no problem. Would absolutely book with Sarah again!”

About: I’ve been an animal lover and hands-on pet caregiver for as long as I can remember. Over the years, I’ve cared for dogs, birds, rabbits, and fish—so I’m comfortable with a wide range of personalities, needs, and routines. My heart dog was a golden retriever I raised from just 8 weeks old through nearly 16 wonderful years. She was family in every sense of the word. I walked with her through every stage of life—including serious health challenges like cancer—and made sure she was surrounded by comfort, love, and dignity until the very end. That experience shaped how I approach pet care: patient, attentive, and deeply compassionate. Since then, I’ve opened my home to fostering and have cared for a variety of breeds and temperaments, including a small German Shepherd mix, Aussie, Border Collie, Plott Hound mix, and others. I’m comfortable with just about all dogs, shy or anxious, and those who just need a steady, calm presence. However I don't currently accept dogs over 50 pounds. When considering boarding, my situation is best for small- to medium-sized dogs or older dogs that don't require a lot of outdoor space for play would be best if they are staying with me. I am only accepting dogs that can be crated when I am not at home. When your pet is with me, they won’t just be “watched”—they’ll be cared for like family. Whether that means walks, playtime, sticking closely to their routine, or simply giving them a safe, relaxed environment, I adapt to what your pet needs most. I want to clarify that my living situation is in a condominium. The only choices in the app are house or apartment and my situation is neither. I live in a small four-unit building in a condominium complex, not far from Cantigny. I am on the board of the homeowners association as well. My unit is on the first floor with a patio and lovely grounds to walk right outside the door. This is a very quiet community. I understand what it takes to entrust your pet to someone you've just met, and I take that trust very seriously. My goal is simple: for you to feel confident and for your pet to feel safe, happy, and loved. I work a sporadic part time schedule at The Morton Arboretum which involves no more than 8 hours per week at this time. I have a lot of free time to dedicate to your pet. When I am with your pet, I will be 100% focused on your pet. I will take no chances with your pet's safety, carefully monitoring the space they are in, toys they play with, etc.
About: I had experience taking care of dogs as a kid. I have been entrusted with checking in on, feeding, loving and caring for dogs of friends, neighbors, and family. I am confident in my ability to handle reactive or anxious dogs. I can read a dogs language (stress, aggression, excitement). I can maintain safety such as making sure the dog is leashed in a busy environment. I keep aware of hazards such as heat, and other dogs. I am on time, and understand what it means to be consistent for routines of dogs, provide clear communication and updates and respect client homes and instructions. I pay attention to detail such as changes in dog behavior, appetite or energy, signs of illness or injury, and owner preferences for routes and pace. I am patient and adaptable. Pet care fits naturally into my daily and weekly routine because I plan my schedule around the pets in my care. I make time for feeding, walks, playtime, bathroom breaks, and regular check-ins throughout the day to ensure pets stay comfortable and on their normal routine. I’m also mindful of providing attention, exercise, and a calm environment so they feel safe and cared for. On a weekly basis, I keep my schedule organized to accommodate bookings, communicate with pet owners, and maintain a clean, pet-friendly space. I also make sure I have flexibility for longer walks, or extra visits when needed. Reliability and consistency are important to me, so I prioritize being available and attentive to each pet’s individual needs. 1) My Home- Daily care: Feed according to the owner’s schedule and instructions Provide constant access to fresh water Maintain routines (walks, playtime, rest) Comfort & safety: Pet-proof your home (no toxic plants, cords, or open exits) Give them a dedicated space (crate, bed, or quiet room) Separate pets if needed to avoid stress or aggression Exercise & enrichment: Walk dogs regularly Provide toys, puzzles, and interaction Adjust activity based on age, breed, and energy level Hygiene: Clean up accidents immediately Scoop litter boxes daily Keep bedding and feeding areas clean 2) Clients Home- Follow instructions exactly: Stick to feeding times, portions, and diet Administer medications if required Respect house rules (furniture, access areas) Routine care: Walk dogs and allow bathroom breaks Clean litter boxes and cages Provide companionship and attention Home respect & security: Keep the home clean and tidy Lock doors/windows and follow security instructions Handle keys responsibly Communication: Send updates, photos, or videos Report any concerns immediately (health or behavior changes)
“Annika is so wonderful! I could not have asked for better care for my girl. I’m so thankful for her help and I know Wink was happy to see her everyday!”


About: Hello! I have been a dog lover my whole life having lived with and owned dogs. Currently, I have an English Bulldog & a well trained German Shepherd. I love outdoor walks and play time - no walk is too long for me with your dog! Also, love to keep them company if they do not want to be alone for long periods of time. Experienced in administering medicines to both cats and dogs. Along with my 2 dogs I live on a hobby farm with chickens, horses & barn cats. In college I worked at Danada Vet in the kennel and assisted on the vet floor with the techs and Drs! Reach out with any questions! Thank you! I’m currently working at my family business in the Wheaton area and most of the work is online or around the suburbs - never gone for more than a couple hours. I can be readily available for walks, care and house sitting. I am experienced in caring for pets in the owners home - happy to keep their routine and habits so their life is easy while you are away!
“Glen did an excellent job taking care of Coco. He gave her a walk, made lunch and all the required water and bathroom breaks. We will leave coco again under the excellent care of Glen.”


“I cannot explain the relief and lack of anxiety I have leaving my girls home and knowing Joan will be there to take care of and love them as much as I do. She is like having a favorite aunt who is always ready, willing and happy to take the kids for a weekend and they love seeing her too. I would highly recommend Joan, I have asked her to watch the girls several times now and will continue. Thanks Joan for everything!”

“Paula is amazing! She knew exactly how to approach our picky German shepherd and adjusted to his needs. She was very calm and comfortable with him. She became his best friend when she walked in with a pup cup in hand. So happy to have found someone reliable we can count on to take care of our fur baby when we go out of town. Thank you!!”

Over 88 pet parents in Winfield have booked dog sitting
Winfield dog parents share their Rover experiences
Barbara was truly exceptional with our beagle, Paige. After recently losing our other beagle, Penny, it was especially emotional to leave her, but Barbara gave us complete peace of mind. She cared for Paige with so much love, kindness, and attention—it was clear Paige was in wonderful hands. Barbara was reliable, communicative, and thoughtful, and her updates meant so much to us while we were away. She went above and beyond, and we are incredibly grateful to have found her. We highly recommend Barbara to anyone looking for trustworthy, compassionate pet care. Paige adores her, and we will absolutely be booking with her again. 🐾💛

Popular requests near you
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1. Search
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The median cost per night for dog sitting in Winfield is $20
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn't happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winfield average 6 repeat dog sitting clients
Dog Sitting FAQs
Frequently asked questions about Rover
Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Winfield on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, there are 13,157 dog sitters in Winfield. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 86% of Winfield dog sitters respond in under an hour.
Dog sitters in Winfield have an average of 14 years of experience. Dog sitters with repeat customers have an average of 6 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winfield.
Rover makes it easy to find Winfield dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
There are 13,157 dog sitters in Winfield on Rover, so you’re sure to find the perfect match for your dog! In Winfield, 96% of dog sitters offer daily exercise, 95% offer medication administration, and 90% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.



















