Dog Sitting Chester
Book a Chester dog sitter to watch your dog in your sitter’s home or yours.
Over 8 pet parents in Chester have booked dog sitting
Chester, 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.
“Lindsay took care of our (cat) babies like they were her own. She took photos of them every time she came to see them, and spent time playing with them as well as feeding and medicating as needed. My cats loved her from the very first introduction. Lindsay is not only an animal lover, she's also a great lady. She surprised us with a list of places and things to try since she knew my husband and I had just moved into the area! We’re definitely looking forward to having her care for our cats in the future.”
“Five stars! I’d double them if I could. First of all Brianna agreed to watch Sasha without even meeting her or us. We all took a leap of faith and I feel it paid off. Through consistent text messages and photos she managed to ease any apprehensions I may have had on this last minute booking. I can’t thank Brianna enough and have her in my contact list if I ever need another sitter. First round draft pick!”
“Sorry Im so later with a review .Chelsea did a very good job taking care of Fred ,she gave him his insulin shots twice a day ,did a good job taking care of his food ,water and tray .Sorry you moved I would have you take care of Fred any day .”
“Allison watched our cat and dog with daily visits while we were away. Our dog is a large German Shepard that can be a bit of a challenge to handle, but Allison quickly put him at ease and established trust with our dog. She also took excellent care of our cat, giving him the type of quality attention that he loves. What stood out to me was how Allison kept a watchful eye on everything during her visits. She pointed out an issue with our rather expensive fish tank and notified me. I'm sure we would have lost most of our fish and coral if she had not taken the initiative to help out. In addition to giving us daily updates and photos of our pets she gives you the sense that everything is well taken care of. Allison far exceeds what I was expecting of a good pet sitter. In my opinion, there is absolutely no one better. I highly recommend Allison. You can feel at ease when you are away. She is a superstar!”
About: With years of hands-on experience caring for pups of all ages, sizes, and personalities, I provide more than just walks—I offer companionship, consistency, and peace of mind. Whether your dog is high-energy, a shy senior, or somewhere in between, I tailor every walk or visit to fit their unique needs. Let’s give your dog something to wag about! I work from home with a flexible schedule, enabling me to be on demand for your pets needs. Whether for walks or drop ins, we can arrange to fit your dogs personal needs. With mountains of experience caring for three of my own, my home is filled with comfort and care items that will help your pup feel right at home.
About: I have worked in the pet care industry, specializing in dogs, since 2013. From daycare and boarding to training and behavior modification- from grooming to veterinary care- I have seen it all and worked closely with a wide variety of experts in these fields. For several years, I even owned and ran my own in-home dog training business before deciding to move to the veterinary side- utilizing my years of experience to now help care for the health of people’s beloved dogs- and cats- in as fear free a way as possible. I am very excited to expand to offer walks and nail trims in this format and for the new relationships I will build! I am currently working part-time so I will be looking to fit in walks between my shifts. Currently I am only looking to book walks, drop ins and nail trims. It is always my goal to treat each dog and cat as if it is my own. I focus on being a strong, calm leader for them and providing them with the respect each animal deserves.
“This was my first time using Rover and leaving my cat with a stranger. Ryan was great and made me comfortable with my decision. Ryan is personable, timely and responsible. He communicated with me daily. I knew I made the right decision when I got a picture of my cat snuggling with Ryan in the big armchair. If Zuul was happy, so was I. Ryan went over and above when my smoke detector battery went bad and started beeping constantly. He knew this upset my cat and came back later in the day to change the battery. I can't thank you enough, Ryan. I definitely recommend Ryan to take care of your furry friend.”
About: Dogs have always been a part of my life. From growing up with dogs, to working with them, they've always been there. I'm a formally trained groomer who has worked in various places around New England. My specially was working with puppies and dogs with anxiety. Both of those need extra patience and time to keep them safe, comfortable, and to make it the best experience possible. I've also worked for a doggy daycare, have done at home walks, and have a number of years experience with housesitting dogs of all ages. I'm a stay at home mom with two young kids, one in school, one will be going in the fall. We spend plenty of time in our yard, getting fresh air and sun. I have a large yard, unfenced, and a good sized home with plenty of space. There are stairs in the front to get upstairs, but no stairs by the backdoor, making it easy for dogs with mobility issues to come inside.
“Jessica was caring and attentive to our kitties! She was able to modify some instructions when my kitten wasn’t eating as well and was very communicative with updates. Thanks, Jessica!”
“Darsy was absolutely amazing with my 16-week-old puppy. She was consistently reliable, punctual, and genuinely caring. It's clear she loves dogs! We hope to rebook her when she’s back in our neck of the woods.”
About: I have done research in animal biology and have worked with difficult breeds like alaskan malamute, Dalmatians, dobermans, etc. When ever a friend/family member is out of town they know I will be around to watch, as my only steady commitment is for 8 hours a day, so I'm able to care for the animal before and after. I make my schedule to fit my pets needs, so in the morning I let my 2 dogs out for potty and little exercise before breakfast.My mom works from home so she will come let them out around noon and at 5 one of them goes on a walk with me while the other stays back in the yard (he doesn't like the outside world)! I will make sure your dogs needs are met depending on breed, size, age, etc. I have worked and owned dogs from 12lbs to 105lbs so I feel well equipped. If your dog is a breed I am not familiar with I will look into the breed beforehand to better understand the dog. Im used to reactive dogs, and am careful to read their body language at all times.
About: Fun, loving, kind to dogs. Love to play with them, been dog walking when my family needs me to experience if dog pulls/starts to run Looking for part time, as long as I can bring my son on weekends it’ll be fine. Weekdays M-F 9am to 2pm availability. Thank you! Enter home through side door and make sure to greet pets before doing whatever is needed to be done. Make sure pets don’t escape. Thanks!
About: I have worked in a veterinarian customer care setting for over 5 years as well as I have 5 years of experience as a dog walker, daycare worker, and boarder. I am able to administer medications including insulin. With my knowledge of vet medicine, I do know when an animal’s condition needs immediate medical attention. I believe safety, transparency, and communication are all really important when taking care of someone else’s pet. All fur friends are beloved members of their families and so, I always try to provide the utmost care to any pet that I work with. I am both an animal care provider as well as a private voice lesson teacher. These two careers work beautifully together with scheduling as the first half of my day is dedicated to animal care and the second half to music. I only care for pets in the owner’s home because I have two dogs at home myself. I make sure that I always leave a space the way it was when I entered being mindful of cleanliness (like not tracking dirt into the house, etc). If a dog seems more timid during the first visit, I make sure to take the time and go slow to give your pet time to warm up to me. If we are outside walking, safety is my number one priority. Making sure that the clasp on the leash/walking gear is secure, and not interacting
The median cost per visit for dog sitting in Chester is $25
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- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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Select a filter and find qualifying Chester sitters!Sitters in Chester average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Chester
Frequently asked questions about Rover
The average cost for Dog Sitting in Chester on Rover is $21.4 per visit (as of July 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 July 2026, there are 2,802 sitters on Rover offering Dog Sitting across Chester. 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 Chester 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 Chester 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 Chester 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 Chester. On Rover:
- 92% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 94% 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.
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