Dog Sitting Chesterfield

Book a Chesterfield dog sitter to watch your dog in your sitter’s home or yours.

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Over 435
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.

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Sitter Profile Image: Journei F.
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Journei F.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
• 9 reviews
5 repeat clients
7 years of experience
Richmond, VA, 23234

About: I’ve been taking care of pets for most of my life. My family and friends have always counted on me to care for our/their pets when needed. I have walked, bathed, fed, snuggled and played with them! I am a full time worker, five days a week, nine hours a day from 9AM to 6PM. And I also have a part-time job that I do on the weekends, but I am still open to any service I could possibly provide for you and your pet! I receive my part-time job schedule weekly schedule every Saturday, so communication is key. I will care for your pets in your home by providing them the care that they need, walks, runs, snuggles, playtime, you name it! If there is anything specific you want me to know or abide by please let me know and I will make sure you and your pet are left satisfied :)

Sitter Profile Image: Janet S.
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Janet S.
from
$13
per visit
5.0 out of 5 stars
• 73 reviews
20 repeat clients
35 years of experience
North Chesterfield, VA, 23234

“Janet is extremely caring and responsible! She goes beyond to be sure my three crazy kitties get what they need even when they are being stubborn (a cat? No way!). She is always my first contact when we need pet care.”

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Elizabeth Z.
Sitter Profile Image: Richard L.
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Richard L.
from
$14
per visit
13 years of experience
Richmond, VA, 23236

About: I own 2 dogs and 2 cats myself, and have taken care of pets for family since I was young. I enjoy being around animals, and promise to take care of your pets as if they were my own. I have 13+ years of experience with dogs, including senior dogs and 5+ years of experience with cats of all personalities. I am currently working freelance, so I have lots of flexibility to take care of your pets. If you have a pet that requires extra attention, I can complete my work in your space, providing any amount of care needed such as timely medication or frequent potty breaks. I have cared for pets in other people homes multiple times and I will ensure your space stays neat and tidy, and will ensure your pet gets the best care in the safety of their own home.

Sitter Profile Image: Jamie R.
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Jamie R.
from
$15
per visit
5.0 out of 5 stars
• 2 reviews
20 years of experience
Chester, VA, 23831

“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”

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Jami F.
Sitter Profile Image: Julia H.
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Julia H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 49 reviews
19 repeat clients
16 years of experience
North Chesterfield, VA, 23236

“Julia was absolutely wonderful! We had her sitting for our very needy cat while we were away for 5 days with our dog. She was super accommodating to our cat’s quirks and our requests. We will definitely prevail on Julia’s services again to include having her look after our elderly dog - she was marvelous, caring and very thoughtful!”

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Margie L.
Sitter Profile Image: Jason P.
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Jason P.
from
$14
per visit
5.0 out of 5 stars
• 2 reviews
4 years of experience
North Chesterfield, VA, 23234

About: While I’m new to Rover, I’ve been caring for pets for friends and family for the past four years, in addition to caring for my own pets throughout my life. My previous dog, a Yorkie, gave me experience caring for a senior pet, including administering eye drops, following medication schedules, and managing a special diet. My current dog, Bella, is a 10-month-old AKC S.T.A.R. Puppy graduate who has taught me plenty about keeping up with energetic young dogs! I also share my home with two friendly, affectionate senior cats, so I’m comfortable caring for pets of different ages and temperaments. I work Sunday through Wednesday, so my Thursdays through Saturdays are completely dedicated to your pup! My black Labrador, Bella, and I typically walk 1–2 miles three times a day. On hotter days, we switch to indoor enrichment and training games instead of long walks. Whether your dog loves an adventure or prefers a slower pace, I’m happy to tailor their stay to their individual needs. Your dog’s safety and comfort are my top priorities. I only accept dogs that are a good fit for my home and Bella, and I always recommend a meet-and-greet beforehand. Whether I’m boarding, dropping in for a visit, or taking your pup on a walk, I’ll follow their normal routine and tailor my care to their energy level and needs. I’ll also keep you updated with photos so you can enjoy your time away with peace of mind.

Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 332 reviews
91 repeat clients
30 years of experience
North Chesterfield, VA, 23236

“Damacia did a phenomenal job caring for our cat while we were away. The brief daily posts helped reassure us, and we were really able to enjoy our trip! Our kitty clearly loves Damacia, who seems to have quite a gift with animals. Fantastic!”

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Catherine H.
Sitter Profile Image: Lauren H.
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Lauren H.
from
$14
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
5 years of experience
Midlothian, VA, 23112

“Lauren did an amazing job taking care of my cat, Luna Laruen was reliable, communicative, and clearly cared about making sure he was happy and comfortable while I was away. Laruen sent me pictures and updates, which gave me so much peace of mind and made it easy to see that Pluto was doing great. When I got home, he was relaxed, happy, and well cared for. I would absolutely recommend Lauren to anyone looking for a trustworthy, caring, and attentive pet sitter. I would definitely book again and plan to do so!”

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Emily F.
Sitter Profile Image: Sarah I.
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Sarah I.
Star Sitter
from
$45
per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
7 years of experience
Chesterfield, VA, 23832

About: I've been dog sitting since covid; things have changed but not the love for animals. Since my start I've dog sat for a wide varity of dogs. Puppies, oldies, big, small. Some requiring a lot of attention to help distract them, some that just sit by the door waiting for their pawrents to come home. From medications to special diets, specific schedules and give attention if you have the extra time. I will treat your dog as my own! Something you can count on is they will be loved and well taken care of. Pet care is my top priority. Making sure they are fed on time and they get plenty of play time and walks while you are gone. I unfortunately can't accept pets into my home as I don't currently live alone. But I'm more than willing to stay over whenever you need me to.

Sitter Profile Image: Nicole R.
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Nicole R.
from
$15
per visit
1 repeat client
15 years of experience
Chester, VA, 23831

About: I am very familiar with all types of dogs! I grew up with german shepherds and most recently have fostered a Great Pyrenees. I live a very active lifestyle and am looking to go on lots of walks with your fur baby! I love giving lots of attention and ensuring interactive time with the animals in my care. Use this link for $40 off your first Rover booking!!: https://www.rover.com/sit/nicolr34569 I'm currently working part-time and have a lot of time, especially during the day, to look after your pet(s). Just give me a heads up what your request is so I can take a look at my schedule. I can go on long or short walks (I prefer longer!) I will provide a safe environment and ensure your pet's needs are more than just met.

Sitter Profile Image: Darnell M.
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Darnell M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 102 reviews
39 repeat clients
14 years of experience
Colonial Heights, VA, 23834

“Many thanks to Darnell for taking good care of our two cats again. Love how even our shy guy hangs out when Darnell's around :) I always know our house and cats are in good hands when Darnell visits!”

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Alexis S.
Sitter Profile Image: Shannon O.
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Shannon O.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 64 reviews
29 repeat clients
20 years of experience
Richmond, VA, 23234

“Shannon did an awesome job on her drop-in visits with our three cats. Our home was also in great shape when we returned; all cat waste was handled properly. There is huge peace of mind knowing that our furkids are happy when we leave home.”

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Mary O.
Sitter Profile Image: Tiffany B.
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Tiffany B.
from
$25
per visit
5.0 out of 5 stars
• 29 reviews
12 repeat clients
23 years of experience
Chester, VA, 23831

“We absolutely love how Tiffany takes great care of our little ones! She always updates us with fun & loving pictures. She is also very quick to respond with any questions or concerns & always on time!”

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Calandria B.
Sitter Profile Image: Tianna L.
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Tianna L.
from
$28
per visit
4.5 out of 5 stars
• 8 reviews
2 repeat clients
5 years of experience
Courthouse, VA, 23832

About: I’ve taken care of my sisters dogs in the past, also owned many dogs growing up. My daughter LOVES them. My availability is pretty open! We would love to meet your furry friends. I’m in college and and i’m not currently working. My availability is open so that I will have plenty of time to care for your furry friend. We love animal's in my home we will treat them as our own of course. My place is clean and taken care of perfect setting.

Sitter Profile Image: Julia P.
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Julia P.
from
$20
per visit
5.0 out of 5 stars
• 16 reviews
3 repeat clients
10 years of experience
Richmond, VA, 23235

“Julia is amazing! She's dependable, easy to communicate with, and it's obvious she really loves animals. We really appreciate the updates she sends and the peace of mind knowing our pup is getting great care while we're away. We're so glad we found her and would absolutely recommend her to anyone.”

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Cindy B.
Sitter Profile Image: Janini C.
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Janini C.
from
$22
per visit
5.0 out of 5 stars
• 19 reviews
5 repeat clients
8 years of experience
Richmond, VA, 23236

“Janini was fantastic!! She did a daily visit/walk. She showed up when she said she would and was in great communication for the 5 days she took care of my dog. I would highly recommend her!!”

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Babs P.
Sitter Profile Image: Michelle C.
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Michelle C.
from
$25
per visit
5.0 out of 5 stars
• 10 reviews
1 repeat client
10 years of experience
Midlothian, VA, 23832

About: I have been taking care of my own dogs since I was young and love to be around all animals! I used to nanny for a family with 5 kids and they had a wonderful dog that I always helped to care for! Feeding and taking him to the groomers and vet appointments…all things that I was lucky to get to help with! I also used to care for 2 cats (both needing to take medication) and a bull dog on a daily basis! I have a Jack Russell (that just passed away) myself that I had for about 10+ years and no kids do she was my only fur baby! I have recently in the past year gotten a brand new puppy named Sugar! She is a beagle/terrier/lab mix and 25 pounds of Adorableness! She is so sweet And absolutely my little girl, as she follows me everywhere and tries to be wherever I am, and always under foot!!! She’s a little skittish and still all puppy at eight months! So I am no stranger to puppy needs at all! I also have Bella, who is a pit/beagle mix and she is a little over a year and a half old! She is 60 pounds of crazy but happy and smart and always at my husband side! What a love bug! But remember, with pets, there is no personal space! Lol I love pets of all kinds and will care for them as if they were my own! Snuggles are free!!! I am currently a part-time private nanny, to a bunch of different families who may need care for their little ones day a week, and my schedule is always changing from week to week so my availability will always be changing. But,I will try to keep my Rover calendar up-to-date as I hope more of you reach out! The plan is is turn this into a full-time gig so I will have probably more availability as time goes on towards the end of this year, but I’m hoping to find some regular clients that will book with me on a consistent basis! Plus, I’m really looking forward to all the pet snuggles! I am always very mindful of the time for feedings and walks…any medication will be given correctly and timely…I will make sure your home is locked up after I leave from a walk and/or feeding! Please know that I will do my best to. Gain the trust of the animal! Cats too! I do highly recommend a meet & greet ahead of time so we can meet pet parents and also meet dog(s)! Let’s them see me and hopefully remember me and feel comfortable with me in their house! (*Please note: House Sitting rates apply to stays where overnight accommodations (a clean bed/space) are provided in your home. If you prefer daytime/evening visits only without overnight stays, please book via my Drop-In rates!)

Sitter Profile Image: Michelle H.
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Michelle H.
from
$25
per visit
5.0 out of 5 stars
• 12 reviews
7 repeat clients
25 years of experience
Chester, VA, 23831

“Michelle was great with my dog. We met ahead of time and I felt great about having her drop in while we were away. My dog got the break he needed and some playtime and treats as well. I would definitely recommend Michelle and would rebook next time I need someone.”

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Amanda H.
Sitter Profile Image: Cynthia S.
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Cynthia S.
from
$15
per visit
5.0 out of 5 stars
• 27 reviews
6 repeat clients
17 years of experience
Richmond, VA, 23235

“Cynthia did a fantastic job taking care of my cat! She made sure she always had water, a clean litter box, and a little play time. She updated me with each visit and gave a thorough report card to let me know how things were going. I would definitely recommend Cynthia as a cat sitter and book her for future trips.”

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Morgan H.
Sitter Profile Image: Christine & Nick G.
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Christine & Nick G.
from
$22
per visit
5.0 out of 5 stars
• 55 reviews
19 repeat clients
20 years of experience
south chesterfield, VA, 23803

“Always trustworthy and my dogs love them!”

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Morgan G.
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The median cost per visit for dog sitting in Chesterfield is $20

Dog parents share their Rover experiences - Chesterfield

1 / 1
5.0 out of 5 stars

Phyllis did an amazing job with our drop-in visits! She watched our 3 cats and dog, making sure everyone was fed, loved, and well taken care of, which included administering medication. The photo updates after every visit brought us so much peace of mind. We will definitely use Phyllis again!

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Janice L.
Drop-In Visits
5.0 out of 5 stars

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!

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Heather S.
Drop-In Visits
5.0 out of 5 stars

Madison was very communicative, consistent, and took great care of my dog. Will definitely book again!

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Bridgette T.
Drop-In Visits
5.0 out of 5 stars

Came thru with a last minute change of plans to take Cody for a nice walk. Arranged a last minute meet and greet. Cody took to her right away. Was timely, sent pics and his activities. Thank you.

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Vickie S.
Drop-In Visits
5.0 out of 5 stars

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!

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Michele M.
Drop-In Visits
5.0 out of 5 stars

Lisa walked into a mess. It's my father's house who had lived in filth unbeknownst to me, as I live out of state. Despite this, she was kind and understanding. Would recommend to anyone!!!

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Jennifer H.
Drop-In Visits
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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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Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - Chesterfield

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Sitters in Chesterfield average 7
repeat dog sitting clients

FAQs for Dog Sitting - Chesterfield

Frequently asked questions about Rover

The average cost for Dog Sitting in Chesterfield on Rover is $22.2 per visit (as of September 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 September 2026, there are 2,360 sitters on Rover offering Dog Sitting across Chesterfield. 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 Chesterfield 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 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 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 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:

  • 94% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 97% 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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