Dog Boarding in Winston, IL
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Winston dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Angela was great! She treated Nino like family and is very genuine about her love of dogs. She also sent a few pics during his stay which was very comforting and appreciated. We will definitely ask Angela to care for Nino again!!”
“Cassandra is awesome! She’s kind, responds quickly, sends pics, and genuinely seems to enjoy my dog! My dog feels right at home at her place with her dogs. We will use her as often as we can!”


“Karen was able to accommodate my last minute request and took good care of Paw Paw and Pepper. Being a dog breeder, she knows the dogs habits instantly and is very caring. Highly recommend.”

“Our girly loved staying with Lottie while we were on vacation! Lottie sent daily updates, and I can tell her and the family spoiled her rotten with snuggles.💕 appreciated knowing she was in great hands!!”


“Amazing sitter! I will definitely be using her again! Keep me informed and was very responsive when I was running late. My dog loved her and enjoyed being around her pups.”

“Taylor did fantastic with our 3 fur babies and they absolutely loved her! She treated and loved them like they were her own and I can’t appreciate enough for that. Gave daily updated pictures of them and kept me updated on how they were doing! Amazing response time! Will continue to rebook with her!”

“She is a really good host. Right from the start itself their dog and our dog connected as they both are of same breed. She was really caring and gave us intermittent updates as well with photos and text of how our dog was doing. Her whole family got connected to our dog really well and provided a homely feeling for our dog. Will definitely recommend them and will like to rover with them again.”

“I can't say enough great things about Ruth! She took excellent care of our 2 dogs while we went on vacation for a week. She provided them with snuggles, walks, and social time and provided us with peace of mind so we could relax. She sent us a few pictures and even some videos! I highly recommend Ruth and we look forward to seeing her again in the future!”

“Our dog Luna loved staying with Flor! They kept us updated with how she was doing with fun photos and videos. They took her on walks and out to play at the dog park. Our Luna also loved their sweet dog and kitten. 😊❤️❤️”

“Was great communication, super friendly, easy to talk to, sent multiple pictures, and the dogs seem to really enjoy their time there. Plan on using her again in the future if available”

“Kylie's an awesome dog caretaker. She kept us updated on how our Lulah has been doing. We highly recommend Kylie if anyone ever needs someone who knows about it all! Thanks again!”

About: I've been around dogs since I can remember. All but one of my jobs have been involved around dogs. I am a Daycare attendant at the bark bark club Currently right now. I do have a normal 9 to 5 job during the week. But I am off on Wednesdays and Fridays. But I do work on Saturdays and Sundays for like 4 to 6 hours. I am very flexible with taking care of your pet in between shifts to the like. I don't mind going back to your house and I haver never had this be problem I will Crate your dogs if you want or I can leave them outside of their crate it all just depends on what you want

About: I have experience caring for dogs of different sizes and personalities, including feeding, walking, playtime, and providing companionship while owners are away. I understand how important it is for pets to feel safe and comfortable in their routine, and I do my best to keep things familiar and stress-free. I’m reliable, attentive, and always treat every dog with care and patience. I maintain a very flexible routine and am home the majority of the day. I do volunteer a few hours daily, but I’m otherwise available to care for pets, provide attention, and keep them on their normal schedule. Dogs in my care will have a stable environment, regular potty breaks, playtime, and companionship throughout the day. I prioritize safety, trust, and a calm environment for every dog in my care. I make sure pets are always supervised, comfortable, and kept in a clean, secure space where they can relax and feel at home.
“JoAnna and her whole family went out of their way to really welcome Loki into their home. A puppy learning to stay away from home for the first time and interact with new people and dogs is a big step. I really appreciate the consideration they gave Loki.”

About: I have recently started dog sitting in my home. I have helped friends and now opening my home to more furry companions to help your family. I am a teacher in Dubuque and have the summers off. During the school year I work from 7:30-4:00 and home full time in the summer months. My home has a fenced in yard and is in the perfect location for walking. I am willing to accommodate any of your family requests for your pet including giving medication, daily walks, play time, and special attention.
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It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
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Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winston.
Rover makes it easy to find Winston dog boarding sitters to provide loving care from their own home. The background-checked, 5-star 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 boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding 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 boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.







