Dog Sitting Chesterfield
Book a Chesterfield dog sitter to watch your dog in your sitter’s home or yours.
Over 453 pet parents in Chesterfield have booked dog sitting
Chesterfield, 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.
About: My partner and I bring over 10 years of dog care experience and 5+ years managing a stable multi-dog group. We carefully watch body language, work to prevent issues early, and keep feeding routines steady so each dog feels comfortable, safe, and well cared for. We’re comfortable working with multi-dog households, different energy levels, and group dynamics. Our focus is creating a safe, structured, and positive environment where dogs can socialize, play, and settle comfortably. My specialty is organization and structure, my partner specializes in socialization and behavioral management. Pet care is part of our daily life. Someone is home throughout the day. We organize our schedule around the dogs in our care so they receive consistent supervision, play, and individual attention. We have a fenced backyard and fenced front yard, giving dogs safe space to move, explore, and play. Inside we provide a dedicated dog room and crates for dogs of all sizes, creating a comfortable and secure place for them to rest when needed. Dogs are thoughtfully grouped by temperament, with attention to proper rest rotation and consistent feeding routines to support balance and comfort. Whether in our home or a client’s home, we focus on safety, supervision, and each dog’s individual needs. We follow established routines, maintain a steady and secure environment, and make sure every dog feels comfortable, cared for, and at ease.
“Above and beyond. The experience was better than perfect. She went way above what was asked . We ran out of food for a pet and she went ahead and bought some . I did reimburse her but she still took time out to handle the issue. It’s so wonderful to know that someone would go above what was required and care for our pets as their own . I will request Jamie again and knowing how well she did and how she cares , makes it easier to go on vacation more frequently. Amazing job Jamie . Thank you again”
About: I've taken care of all kinds of animals since I was 16. Dogs, cats, fish, birds, lizards and a rabbit. I have experience in older animals who need medication multiple times a day. I'm currently working part-time with few hours so I have a very flexible schedule and will have plenty of time to meet the need of you and your pet! I stick to a strict schedule if any kind of medicine is involved. Aside from that I am more laid back in my approach to pet-sitting. I love giving treats and extended play times!
About: I am a young professional with two orange cats of my own! I've been watching animals for my family, friends, and neighbors since I was a kid; I love cats and dogs of all colors, breeds, shapes, and sizes. I'm currently between jobs, so I have plenty of time to play with your pups or satisfy your unique care needs! I'm lucky to have a flexible schedule, so I strive to accommodate others' schedules to the best of my ability. Safety is paramount for me. As a pet-owner myself, I strive to meet the needs of each pet without putting them at risk of harm or distress.
“My cat Charlie was in the best hands! She was punctual, professional, communicative, and attentive. She went above and beyond to make sure Charlie got the best possible care. During my week away from home I trusted that my pet was being cared for and I didn’t have to worry one bit. Would absolutely book again and recommend to friends!”
About: What sets me apart is my calm, low-stress home where I host max 2 compatible dogs at once. Perfect for anxious, selective, or reactive pups who need peace over chaos. I also offer solo-stay pricing for dogs who need to block my second spot. My experience shines with senior dogs (gentle mobility support, meds) and high-energy mediums (structured play without overwhelming them). I work less than 10 minutes from home and have a flexible schedule that allows me to check in during my breaks for walks, playtime, and potty breaks. While I’m away, I use indoor cameras to monitor pets and ensure their safety and comfort. I’m fully available and home on weekends, so your pup will get plenty of attention, care, and activity throughout their stay. I don’t have any pets of my own currently. I have a nice size fenced yard and I love taking pups on long walks in my neighborhood or at the local dog park if possible. You can also book my backyard on Sniffspot!
About: About me: I’m very compassionate with peoples pets, I am very skilled in the pet sitting and daycare environment as well as the medical side and grooming side. I think what really sets me apart from everyone else is that I am a licensed pet groomer as well and if you need any sort or grooming i would be able to groom your pets as well so when you pick up your pets from a day with me they will smell great and look amazing as well. I also have pets of my own which means I know how much love and play time pets need and what it takes to care for someone else’s beloved pets. If your looking for someone who has a whole lot of experience and variety of animal field experience hire me and you won’t be disappointed.
About: Growing up, I have always found it easy and rewarding to take care of animals I have learned to be very attentive and receptive to the needs of furry friends and just find them to be such nice listeners in return 😂 We used to have a house full of dogs and cats and it was more a pleasure, than a chore, to get to interact and take care of them. All that to say, I am completely confident and comfortable in my ability to assist in any way when it comes to our four (or 1,2, and 3) legged pals! I just moved to the Richmond/Midlothian area so I’m looking for some good chances to earn some savings doing what I love!! I have pretty open availability! I don’t sit at my house only for the fact of my two French and English bulldog babies! They tend to get tense and wouldn’t want any discomfort for any other pet! I am very respectful to the needs of the client and their furry companions!!
“Lilliana was excellent and extremely professional. She was on time and went the extra mile to make sure our pets were taken care of. I will definitely be using her services again.”
“Hailey was wonderful! After another sitter fell through last minute, she was able to help us with only a couple hours notice. She gave us updates and pictures every visit and even gave our Kona a bath. She was also able to get Kya to go outside without a leash. I’m so glad we found her!”
About: As a medical student with diverse experience handling everything from farm livestock to in-home pets like my bunny Ruby, I provide uniquely adaptable, responsible care. I am balancing medical volunteering and summer school until returning to my full-time job this August, maintaining an organized, highly adaptable schedule for your pet. In either home, I strictly follow your pet's exact feeding, medication, and exercise routines. I prioritize active engagement, regular updates, and an immaculate environment, ensuring they remain safe, calm, and happy under my responsible care.
About: I grew up around dogs, caring for our family pets. As an adult, my own dogs are the highlight of my life. I spend my time trying to give dogs even a fraction of the love and devotion they give to us! I'm experienced with caring for all sizes and breeds of dogs from all walks of life. I'm happy to adapt to any needs, including training reinforcement, pacing, interacting or not interacting with other dogs/people etc. I also have experience with training puppies and caring for senior dogs(as I have one of my own). I work a full time corporate job with some flexibility on a case by case basis. Most of my availability is in the evenings and weekends, but I'm more than happy to discuss special requests! I'm happy to walk your dog through a familiar area in the neighborhood or even to a nearby dog park if desired. Happy to accommodate what makes you and your fur baby happy!
About: From wolfhounds to chihuahuas, I have petsat them all! I have experience with giving medicine, assisting senior dogs with mobility, exercising, playing, feeding, and giving all the affection needed. Petsitting would be split with my workday on Monday -Wednesday. I can come in the morning, during my lunch break, and spend as much time as needed after work with your pet. Friday through Sunday I can do as many visits and walks as necessary. It is safer and better to build trust with any animal if there is a meet & greet before petsitting. This helps me know the routines of your household and shows the pets that I'm not a stranger when I come to care for them. Sticking to the routines/key words they know, engaging them with praise, play, or treats, and letting the dog/cat have space when needed - are all ways to help your pet be at ease.
About: I’ve always loved animals and grown up around so many dogs and cats. I enjoy providing pets with great care and treating them like my own. I have experience with animals of all ages and I’ll take the time to make sure they feel comfortable, happy, and cared for! I’m currently in graduate school and have class until 11:50! I’m free before/after and free during the weekend as well. Overall, my schedule is very flexible. When caring for pets in their own home, I aim to keep them as comfortable as possible and maintaining their normal routine. I follow their feeding, walking, and playtime routines, while giving them plenty of affection.
“Lauren was really great, especially given our cat is very skiddish/scared and runs under the sofa at the slightest noise. Thank you for being caring and compassionate. When we go out of town again, Lauren will definitely be our selection. We highly recommend her.”
About: Hey everyone, I’m Cailey! Ever since I can remember I’ve had a deep passion for all types animals! There’s not a single day in my life where I didn’t have a pet to call my best friend. So I figured I should spread my love and help others by caring for their pets! Almost everyone can agree that pets are a part of the family, so I assure you that your babies will be cared for and loved just as if they were my own. I have a doggie of my own named gunner and a cat named pumpkin, whom I absolutely love and adore. They are both super welcoming and love meeting new friends! We are looking forward to meeting you and your adorable pets. We can’t wait to give them a home away from home! 🐾 Caring for pets is currently my only job, as well as my husband helps out when he’s not at work, so there won’t be a moment where your pet is left alone! With my previous experience, I can easily give any medical care your pup may need, such as medication or any daily medical treatments they may have.
About: I have had all sorts of animals throughout my life. I’ve never worked with dogs professionally but I’ve had multiple family dogs ranging from Chihuahuas to Pit bulls and I loved and cared for all of them. I currently have 2 Pit bulls that are loved and happy. I also often help pet sit in the neighborhood. During the school year I will be in class from 8 to 3 but after that I have plenty of time to walk and/or care for your pet. I have no other priorities so taking care of your fur baby will be my main focus. I am typically well liked by dogs and I am patient with dogs that are still in training so if needed I can go at your dogs pace making them more comfortable.
About: Before I moved to Richmond I rescued animals in WV . I would have puppies in & out for years, nursing them & giving them to proper homes ❤️ I currently work full time so this will be an evening & weekend extra curricular for me , however I do not see this as a job, rather a hobby. Currently I just plan on walking , checking in , feeding etc . I’m currently pregnant & trying to find ways to exercise to improve my health :)
The median cost per visit for dog sitting in Chesterfield is $20
Dog parents share their Rover experiences - Chesterfield
This was our first booking with Rebecca, and it went great! She did two drop-ins with Zeus over the weekend. She was communicative and prompt, and provided updates with pictures and a summary of their time together. We look forward to working with her again in the future!
They are the BEST! I had a really last minute request and they responded within minutes to confirm their availability. Its really give me peace of mind knowing my pups will be taken care of, exactly as I ask, at the exact time we schedule. Thank you all so much!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book dog sitting
1. Search
Browse profiles of sitters near you who offer dog sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog sitting - Chesterfield
Select a filter and find qualifying sitters offering dog sitting.Sitters in Chesterfield average 7 repeat dog sitting clients
FAQs for Dog Sitting - Chesterfield
Frequently asked questions about Rover
The average cost of Dog Sitting in Chesterfield is $22 per visit as of October 2026. Most bookings cost between $14 and $31 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 2,357 sitters on Rover offering Dog Sitting across Chesterfield. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 Chesterfield 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 .
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 , which provides up to 25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
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 Chesterfield 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 Chesterfield. On Rover:
- 91% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 96% 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 , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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