Dog Sitting Chester

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

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Over 168
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.

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Sitter Profile Image: Sarah I.
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Sarah I.
from
$25
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
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 do currently work but my schedule is constantly changing so I have a lot of freedom to change it as needed. 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: Hailey T.
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Hailey T.
from
$30
per visit
4.9 out of 5 stars
27 reviews
15 repeat clients
15 years of experience
Chester, VA, 23831

Great communication, went above and beyond to care for our Kitties- she even took the trash out!! Thankful to have Hailey look in on our babies while we traveled for Thanksgiving. Will book again!

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Tommie M.
Sitter Profile Image: Amanda W.
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Amanda W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
55 reviews
17 repeat clients
15 years of experience
Chesterfield, VA, 23832

Amanda is great with our shy tortie, Kallie! She goes above and beyond with extra pets and attention. We always come home to a happy cat and a clean home. I would definitely recommend her!

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Jackie N.
Sitter Profile Image: Alecia B.
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Alecia B.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
58 reviews
20 repeat clients
20 years of experience
Chester, VA, 23836

Alecia is awesome with my pup! She is very dependable and reliable. 10/10 would recommend!! There hasn’t been a time I’ve needed Alecia and she hasn’t been available. Even with last min requests.

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Pepper Y.
Sitter Profile Image: Sara T.
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Sara T.
from
$15
per visit
28 years of experience
Chester, VA, 23831

About: I've never been without pets in my life. My family and I have always been avid animal lovers, and I've been lucky enough to raise dogs, cats, snakes, and even horses! Growing up, we always had at least two dogs, and oftentimes, a cat as well. Currently, I have two cats and a pit bull of my own. Over the past 8 years, I've worked as a pet sitter for friends, family, coworkers, and neighbors. I'd like to offer my services to those who may not have someone they can lean on when they're busy! I work 3 days a week as a full time EMT and volunteer with a local fire department in my free time. If you have any questions about my services, me, or my availability- please don't hesitate to reach out! :) As a full time EMT, my work schedule is very forgiving. I have four days off each week, which are Monday, Wednesday, Saturday and Sunday. I can very easily fit pet care in on those days, and by request, can sometimes squeeze in morning care on Tuesday, Thursday, and Friday. With a dog and 2 cats of my own, I do not offer boarding services. I have plenty of experience pet sitting in your pet’s natural habitat; home visits are no issue for me, and I think it’s the best way to ensure that your animals are as comfortable as can be while you’re away.

Sitter Profile Image: Crystal A.
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Crystal A.
from
$25
per visit
5.0 out of 5 stars
10 reviews
10 years of experience
Chester, VA, 23831

About: I have taken care of dogs ranging from 10 pounds to 160 pounds my entire life. I have owned chihuahua dachshund mix, akitas, huskies, and German shepherds; so I understand big breeds as well as smaller ones. I have helped family members and neighbors with their dogs growing up with house sitting and dog walking. I know how important furbabies are to families, and treat each and every one as I would my own. I currently work full time with every other Monday off. I go to work about 7 am and get home about 430 pm. I do have volleyball leagues on Monday Wednesday and Friday nights that I am gone for 2 hours between 6-11pm as it varies based on game time. I love to hike and be outside so taking the dogs for walks a non issue. I treat all furbabies as if they were my own. I adjust my schedule accordingly to accommodate the animals as best as I can. I have given insulin shots and medication to animals and am comfortable with it.

Sitter Profile Image: Brandie S.
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Brandie S.
from
$25
per visit
5.0 out of 5 stars
25 reviews
13 repeat clients
20 years of experience
Chester, VA, 23831

I am a new client for Brandie . She was very good to my Blue. He responded well to her, and she put the extra effort to make sure he was comfortable while I was gone.

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Paula L.
Sitter Profile Image: Grace L.
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Grace L.
from
$18
per visit
5.0 out of 5 stars
38 reviews
14 repeat clients
17 years of experience
South Chesterfield, VA, 23834

Grace took great care of my kitties. This is my second time booking her, and just as last time she followed all my instructions and it seems like my cats like her.

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Jacob K.
Sitter Profile Image: Linda A.
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Linda A.
from
$32
per visit
5.0 out of 5 stars
22 reviews
4 repeat clients
30 years of experience
Chester, VA, 23831

About: After recently relocating from Dallas, I’m excited to bring more than 30 years of pet-care experience to my new community. Back in Dallas, I ran an in-home pet-boarding business for a full decade, caring for pets of every breed, size, and personality. Over the years, I’ve also fostered countless dogs through local rescue programs, helping shy, senior, and special-needs pups find their confidence — and their forever homes. However, my experience goes far beyond cuddles and playtime. I’m skilled at administering oral, topical, and injectable medications, and I'm comfortable caring for pets of all ages, from energetic puppies to aging companions who need a little extra TLC. I believe every animal deserves calm, consistent care that keeps their routine — and their spirits — steady while their people are away. I'm a writer/editor that works remotely, and I have a stay-at-home dog dad to hang with my personal fur kids while I'm away. Point is, I have the a ton of flexibility. I care for your pets just as YOU care for your pets. That is, you set their schedule (feeding, bedtime, play, etc.), and I carry it out while you're away.

Sitter Profile Image: Karen T.
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Karen T.
from
$20
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
16 years of experience
North Chesterfield, VA, 23234

Karen was prompt with her visits while watching our dog over the weekend! She is very professional with communication and very reliable when caring for our dog. We are excited to use Karen again in the future!!

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Anne A.
Sitter Profile Image: Tianna L.
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Tianna L.
from
$28
per visit
4.4 out of 5 stars
7 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: Hana J.
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Hana J.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
16 reviews
4 repeat clients
17 years of experience
Colonial Heights, VA, 23834

Hana is amazing! She’s so flexible and understanding when it comes to schedules and demands of each animal in the home. She truly cares about our animals (she will leave our tv on for our dog so she isn’t lonely) and does enrichment treats without us even asking her to. I trust her with our babies 100%

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Ashley D.
Sitter Profile Image: Melissa M.
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Melissa M.
from
$30
per visit
5.0 out of 5 stars
1 review
2 repeat clients
30 years of experience
Chester, VA, 23831

About: I've cared and been around pets and dogs of all breeds all my life. My family has always had dogs so I have experience feeding, grooming, playing, walking, administering simple medication, and basic training. I'm a mom of 7 that works part-time, with little ones in school, so I have the means, time, professionalism, and drive to play and care for your four legged family member, when your unavailable to.... And your able to rest assure that they are well taken care of :) When caring for pets I am able to visit and care for them in their natural setting.... Of their home, so they more natural and relaxed. Please reach out if your interested in weekend boarding at my home.

Sitter Profile Image: Samantha B.
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Samantha B.
from
$35
per visit
5.0 out of 5 stars
31 reviews
17 repeat clients
30 years of experience
Chester, VA, 23831

Sam is so thoughtful & in touch with our boys needs. She loves animals and it showed in her interaction with our boys. We will definitely book again!

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Areca H.
Sitter Profile Image: Airlea e.
Verified Enhanced Background Check
Airlea e.
from
$25
per visit
5.0 out of 5 stars
3 reviews
13 years of experience
Richmond, VA, 23237

About: I have over a decade of professional pet care experience as well as a lifetime of personal pet care experience. I prefer to work with the elderly or medically complex pets as I know they need special attention, adherence to routines, and a calm environment. I focus on providing fun daycare and boarding for pets that don’t do well in regular boarding facilities and require a more home-like experience. Prices are negotiable after a meet and greet. Please fill out your profile in full before meeting! Incomplete/no profile image profiles will not be given my address. I work from home so I spend a majority of my day with my pets and guest pets. Dogs are given mostly free range inside and allowed outside into the huge fenced yard many times a day. They get playtime with other pets and alone time when needed. Our yard is fenced and our house is doggy proofed to avoid trash cans, toilets, and non-chewable items from being accessed. Dogs are crated when they can’t be supervised.

Sitter Profile Image: Journei F.
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Journei F.
from
$14
per visit
5.0 out of 5 stars
6 reviews
3 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: Joanette C.
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Joanette C.
from
$40
per visit
4.9 out of 5 stars
42 reviews
18 repeat clients
9 years of experience
A chesterfield, VA, 23834

Jo is amazing!! My dogs are highly anxious and do not take well to strangers in my home but they absolutely love her! When I used to leave for work they would be depressed but now they aren’t, they actually start playing when I leave which is comforting as I am an anxious dog mom. I trust my dogs with a total of four people and Jo is one of them. She is always so polite and respectful. I would recommend her to anyone looking for a trustworthy pet sitter!

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Amanda M.
Sitter Profile Image: Allejah K.
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Allejah K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
6 reviews
7 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

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 from home so I'm very flexible. I'm available during the day for walks/drop-ins/daycare, evenings/weekends for boarding. Dogs are family here; my routine revolves around their comfort. 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!

Sitter Profile Image: Amanda M.
Verified Enhanced Background Check
Amanda M.
from
$30
per visit
5.0 out of 5 stars
66 reviews
17 repeat clients
17 years of experience
Chester, VA, 23831

Amanda went above and beyond for my two cats while I was away over the holidays! She is respectful, professional, and a great communicator. Every day she would send me 20+ photos, to include photos of their food dishes and play time so I knew they were being well taken care of! She even cleaned up around the house so I didn’t come home to litter all over the floor! I was very pleased with her services, and I will definitely be a return customer!

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Ellie S.
Sitter Profile Image: Victoria V.
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Victoria V.
from
$20
per visit
1 repeat client
10 years of experience
Chester, VA, 23831

About: I have grown up with both cats and dogs and currently live in a household with four cats. I have worked at a veterinary clinic for well over 3 years now, so I am comfortable administering medications including liquids, pills and injections. I am knowledgeable about common pet conditions and illnesses as well. I currently work full time but I do go in late/get off early several days during the week plus I don't work Thursdays and only half a day every other Saturday. I will happily take care of your pets days I don't work or before and after my shifts! This of course wouldn't be my first time petsitting in someone else's home that I didn't know well, so I know there are boundaries that are necessary to respect and would never do anything that you have not allowed ahead of time.

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The median cost per visit for dog sitting in Chester is $20

Dog parents share their Rover experiences - Chester

1 / 1
5.0 out of 5 stars

Tiffany was a joy to work with. Great response time and punctual. She dealt well with our dog’s feeding requirements. Took very good care of our dog, and we really appreciated it.

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Renee P.
Drop-In Visits
5.0 out of 5 stars

Amanda was great with my dogs, and she had such a wonderful personality! I truly appreciated her care and would definitely book with her again.

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

Phyllis works well with my dog even though she can be a little sassy. I appreciate her patience and making sure my dog is taken care of. I highly recommend her.

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Angel C.
Drop-In Visits
5.0 out of 5 stars

We loved how Sabrina took care of our pets. She followed all of our instructions for their care and on a timely basis. We will probably be asking for her again.

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Suzanne F.
Drop-In Visits
5.0 out of 5 stars

Indiana was great. I had to go out of town last min and she was there for us. My dog Mya loved her

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Sarah r.
Drop-In Visits
5.0 out of 5 stars

Bella was very responsive and dependable. I have a very scared dog and she was very patient & kind with her. Will definitely book with Bella again!

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Shelby W.
Drop-In Visits
5.0 out of 5 stars

Cassidy was very professional and trustworthy! She did 2 drop ins and I was nervous but she made me feel comfortable!

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Liz G.
Drop-In Visits
5.0 out of 5 stars

Charlotte responded promptly with the shortest time possible and gave me some peace while I was away for an emergency. Tech was well well taken care off. Definitely recommend her for your pur

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Anita A.
Drop-In Visits
5.0 out of 5 stars

Brandie always does an amazing job with our pets. We know they’re in good hands when Brandie is taking care of them.

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Kelsey G.
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
5.0 out of 5 stars

She took a last minute booking as I had to run out for an emergency, A friend told me about her and she was nothing less than awesome Thanks!

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The V.
Drop-In Visits
5.0 out of 5 stars

Stephanie took extra special care of our 3 dogs. Even did some cleaning! I am so appreciative! Would love for her to take care of our babies again!

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Vickie B.
Drop-In Visits
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Sitters in Chester average 7
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 $19.98 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 2,339 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:

  • 93% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 98% 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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