Dog Sitting in Chester

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

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Top rated Chester dog sitters

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: 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

Brandie came and checked on my two dogs, and did a great job! She made sure to communicate clearly and took lots of photos of the dogs playing.

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Lina C.
Sitter Profile Image: Tiffany B.
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Tiffany B.
from
$25
per visit
5.0 out of 5 stars
28 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: Rebecca R.
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Rebecca R.
from
$19
per visit
5.0 out of 5 stars
1 review
3 years of experience
Chester, VA, 23831

About: I specialize in dogs that need a little extra grace and a lot of patience, but I also love a social butterfly! I know firsthand that not every dog is an easy walker; having raised a reactive dog and managed the 'pulling power' of a Great Dane and a Lab, I have the confidence to handle any situation. ​For social pups, I love encouraging their friendly nature and ensuring they get plenty of positive interaction. I am very observant of canine body language and use consistent treat training to keep every walk safe and fun. Whether your dog is a social socialite who loves making friends or a sensitive soul who needs a sitter who truly 'gets' reactivity, I provide a calm, confident environment tailored specifically to them. Pet care is a staple of my daily routine! While I work a standard 9-to-6 business day 5 days of the week, I am wide awake and ready to go for those early 5:00 AM or 6:00 AM morning walks. Your pup will get plenty of exercise and attention before I head out, and I’m back in the evenings for more play, dinner, and potty breaks until 10:00 PM. I specialize in house-sitting and recurring schedules, ensuring your pets have a consistent best friend to look forward to every morning and night. Whether I’m staying at your place or visiting for a drop-in, your pets are treated like family. My approach combines physical exercise with mental engagement—I love incorporating short, positive training sessions into our day to keep their minds sharp. They’ll get plenty of 'tummy rub' downtime and scheduled feedings, but they’ll also get the structure and play they need to stay happy and tired out. Your dog won't just be watched; they’ll be active, engaged, and thoroughly spoiled.

Sitter Profile Image: Hailey S.
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Hailey S.
from
$15
per visit
5.0 out of 5 stars
3 reviews
15 years of experience
Chester, VA, 23831

Thank you for all your help you did so great with my precious Hank!

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Jordan C.
Sitter Profile Image: Crystal A.
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Crystal A.
from
$25
per visit
10 years of experience
Chester, VA, 23831

About: I have taken care of dogs ranging from 10 pounds to 110 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: 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.

Sitter Profile Image: Abreya K.
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Abreya K.
from
$30
per visit
4.8 out of 5 stars
48 reviews
18 repeat clients
23 years of experience
Chester, VA, 23831

Abreya did well with my cat.

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Kiana D.
Sitter Profile Image: Hana J.
Verified Enhanced Background Check
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: 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: Leeyah E.
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Leeyah E.
from
$14
per visit
5 years of experience
Richmond, VA, 23237

About: My love for animals started at a young age! My mom and I were apart of an organization that transported dogs from kill shelters in the South to non-kill shelters in New York. I have 5 dogs, a horse, and a rabbit. I previously worked at a boarding facility for cats and dogs. I currently work as a vet assistant under Mission Pet Health. I am a junior at VSU and a first year student at Penn Foster to become a veterinary technician. I am dedicated to helping, improving, and supporting the level and quality of care that my clients need! I currently work part time as a veterinary assistant. I have a flexible schedule where I can assist clients with pet-sitting. I am available on weekends and holidays as well! I do not plan on bringing other dogs in my house because I have 5 dogs already, however the high quality of care that I provide for my own dogs will reflect the care that I provide for others!

Sitter Profile Image: Grace L.
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Grace L.
from
$18
per visit
5.0 out of 5 stars
37 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: Abrianna C.
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Abrianna C.
from
$14
per visit
4 years of experience
Bellwood, VA, 23237

About: I have experience with dogs of all ages and sizes! I raised two dogs from puppies to adulthood and trained them myself. At the time I lived on a farm and insured to keep all of my animals (3 dogs included) safe and well behaved. I am absolutely in love with animals (as many should be) and miss having that part of my life. I am a student and work part-time. Due to this, I have to be organized and prepared. As I have worked/lived off the land, I also am not afraid of getting my hands and knees dirty. I look forward to meeting you all and your beautiful fur babies! I am currently working part time and take classes purely online. This gives me a mostly free schedule and the availability to take care of your animals! I believe a dog's comfort is top priority. I always aim to respect a dog's boundaries by reading their body language and presenting myself as not threatening.

Sitter Profile Image: Hailey T.
Verified Enhanced Background Check
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: Sarah I.
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Sarah I.
from
$25
per visit
5.0 out of 5 stars
5 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: 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 truly the best person to give care to your pet. She is extremely caring and involved in the whole process of really making sure that your baby gets the best care possible. My Bassett Hound puppy is so happy to see her when she comes to visit! If you really want someone you can always trust and definitely depend on, Alecia is your best bet, HANDS DOWN!!

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Matt T.
Sitter Profile Image: Rebecca B.
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Rebecca B.
from
$20
per visit
5.0 out of 5 stars
43 reviews
18 repeat clients
20 years of experience
Chesterfield, VA, 23234

We came into town from LA for a wedding and Rebecca took care of my sweet girl like she was her own! Best idea ever to book time with her! In unfamiliar settings it was great to know that my pup was in caring and good hands, if we come back Rebecca will be seeing Wynn again!

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Shay D.
Sitter Profile Image: Amanda W.
Verified Enhanced Background Check
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: 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 did a great job caring for our little old cat Queequeg. She fed her, gave her her medicine, and even monitored her bowel movements for us without question. Due to Quee having IBS her tummy is very fragile, and we don’t feel comfortable leaving her care to just anyone.

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Emily K.
Sitter Profile Image: Linda A.
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Linda A.
from
$32
per visit
5.0 out of 5 stars
21 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: Allejah K.
Verified Enhanced Background Check
Allejah K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
6 reviews
5 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!

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Over 166
pet parents in Chester have booked dog sitting

Chester dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

This is our second time with Phyllis. It gives us such peace of mind while on vacation knowing that our pets are well taken care of. She is great with our 3 kitties and our anxious german shepherd. Great communication with photos and texts. We highly recommend Phyllis!

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

I knew I liked Amanda as soon as she came over to meet our senior dogs before our booking. All 3 responded to her so beautifully. She was communicative and sent pics every day. She was reassuring and calm when one of them had an upset stomach. I highly recommend her to anyone but especially any that has a dog that needs some extra attention. She's awesome!

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Lori L.
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

Sabrina did a great job. She communicated with me throughout the time she was sitting for my dog. I would highly recommend her.

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Verlecia S.
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
5.0 out of 5 stars

Caitlin does such an amazing job with our 3 huskies, I’m always at ease when she comes to check on them!

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Kaitlyn M.
Drop-In Visits
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The median cost per night for dog sitting in Chester is $20

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Sitters in Chester average 7
repeat dog sitting clients

Dog Sitting FAQs

Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Chester on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Chester dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 2,387 dog sitters in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 88% of Chester dog sitters respond in under an hour.

Dog sitters in Chester have an average of 15 years of experience. Dog sitters with repeat customers have an average of 7 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Chester.

Rover makes it easy to find Chester dog sitters to provide loving care from their own home. The background-checked, 5-star dog 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 sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

There are 2,387 dog sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 97% of dog sitters offer daily exercise, 98% offer medication administration, and 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog 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 sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.