Dog Boarding in Chester, IN
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Top rated Chester dog boarders
“Penny is amazing! My dog had the best time, she took such a great care of him. She was sending me photos and up dates all the time. Would definitely recommend Penny!”
“Laurie was outstanding with our dog, Remy. She sent photos and updates everyday. We felt like Remy was part of Laurie’s family. He looked comfortable and loved in the photos we received. We will absolutely be going to Laurie again when we need boarding for Remy.”
“Our pup Lily looked very comfortable at Gabes place. She is a nervous pup to begin with so it was a relief to see her at ease. I also appreciated the text update with pucture. Thank you Gabe!”
“Goldie, being a rescue, is a really anxious and apprehensive dog. Lydia was awesome with her, she has the expertise (being a foster for a rescue) to make the dog feel comfortable and safe. Goldie was really spoiled in her stay, we also ran into a delay in our trip and Lydia was awesome and understanding. I totally recommend her for sitting your dog!!”
“Very thankful to have found a boarder close to home. Pam made our dog feel at home and I could tell she enjoyed her time there. I especially like how Pam took the time to ask questions about our dog to get to know her and her likes and dislikes.”
About: i have lots of experience walking dogs and pet sitting! with my rover experience and dog walking for the animal shelter i can assure you that your pet would be in good hands! i work third shift four days a week so i have a very open schedule for walks and drop ins. my best times are 9am-noon and 4pm-7pm but i am open to requests at any time:) while walking dogs i ALWAYS keep them on leash. i’m comfortable helping with whatever you need whether that’s just hanging out or maybe brushing your pet:) just ask!
About: I became a dog mama long before I became a human mama. I know how important trust is when it comes to your pets, so I prioritize clear communication, regular updates, and genuine compassion, so you can relax knowing your furry family member is in loving, capable hands. 🐾 I currently stay at home with my boys so I am available to give lots of love and attention to your fur babies while I do the same to my own! I have a large fenced in backyard, a quiet neighborhood for walks, 2 toddler boys who will help with lots of playtime, and a small dog who loves company!
“Samantha was fantastic. She took great care of our Irish-doodle, Fitz. She was great about communicating and sending pictures. Her home was very clean and they have a very large fenced in back yard. We will definitely use Samantha again.”
“Haylie was so wonderful to work with! She sent me updates and pictures throughout my trip and allowed me to extend Seeley's stay with her family on short notice when we had some unexpected issues. This was his second time staying with Haylie, and I am sure it won't be his last!”
“Jake enjoyed playing in the fenced in yard. We don't have one, unless we take him to the dog park he has to be on a leash. He had a good time. Thank you Xander for taking such good care of him!”
“Sydney and Andrew took great care of LeRoy Jenkins and I have already booked them to watch him on a subsequent visit. Sydney is very responsive and sent lots of pics / videos to let me know how LeRoy Jenkins was doing, which eased my anxiety so I could enjoy my trip :)”
About: I have been taking care of animals for my whole life. I currently own two Ferret, two dogs, and two cats. I love training dogs I am actually trying to save money to start taking certifications for dog training. I am a disabled human, so I spend almost all day at home able to care for animals. Dogs will go outside to potty every 4 hours unless special instructions are given. My dog Ruger will not be around any male dogs that I watch. I will only accept to watch a dog if the owner also bring their dog a crate, their own toys, and some of the dogs food. I will not accept dogs that have any aggression.
About: With four years of experience as a veterinary assistant, I provide knowledgeable, compassionate pet sitting you can trust. I understand how stressful boarding can be for both pets and their owners, so I focus on creating a calm, comfortable environment where your animals feel safe and loved. From energetic puppies to senior pets and those with special health needs, I have hands-on experience caring for dogs and cats of all ages and conditions. When you can’t be there, you can feel confident knowing your pet will be treated like family—with patience, attention, and genuine care. Pet care fits seamlessly into my daily and weekly routine, especially since I work from home and am able to provide consistent, attentive care throughout the day. Each day, I ensure pets are fed on schedule, receive any necessary medications, and get plenty of enrichment and one-on-one attention while I monitor their overall well-being. Because I’m home, I can easily accommodate different routines. I focus on maintaining each pet’s normal routine to keep them comfortable and stress-free. I provide attention tailored to their personality and needs. For cats especially, I prioritize a calm, low-stimulation environment, respecting their boundaries while ensuring they feel safe and engaged. When caring for pets in a client’s home, I keep their space clean, follow all instructions closely, and provide daily updates so owners feel reassured and connected while they’re away.
About: I am an animal lover. My husband and I have two well behaved doodles. They are therapy dogs. We work a typical 9-5, but your dogs will be walked every evening. We have a fenced in back yard with ample room for the dogs to play. I am a research scientist at WPAFB. My husband is a mechanical engineer at Henny Penny. Your dogs will be treated like our babies. We both work full-time but we are home every evening for walk and cuddles. We have two therapy dogs who will love to play and keep your dogs company. I have a fenced in back yard and two doodle therapy dogs who can play with your dogs and keep them company while we are at work.
About: I have been working at a pets hospital before when I was in China. I have a Rottweiler right now,she is 5 years old. I play with her after I got home. I can take care of your pets on Monday-Friday at 5:00pm-8:00pm,Saturday and Sunday are all day long available,holidays are also all day long available.No overnight! I have a big yard and fence,my dog is very independent,I always play with my dog,she loves the ball and rope.we often play tug of war.
Chester dog parents share their Rover experiences
Nessie loved her time at Penny's and enjoyed having lots of other doggies (and kitties!) to play with. Penny was prompt and upfront in her communication and provided a full check-in and check-out report so I felt in-the-know! It was clear Penny is experienced and intentional in her work as a dog sitter and we appreciated the care she gave to our dog.
Penny loves dogs and will take good care of yours! She was great with my very sensitive girl and made sure she was comfortable and right at home. She even went out of her way to make Mika’s food extra yummy when she wasn’t showing much appetite. Excellent and quick communication too. Thanks Penny!
First time using Rover. Penny was great with our Alice. We are new to leaving her with other than family. Alice seemed very happy there with Penny. We liked the updates and pictures of our little girl. We would recommend Penny to any dog parents. Thank you again for taking such good care of her.
Popular requests near you
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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 Chester.
Rover makes it easy to find Chester 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.
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