Pet Sitting in Chester

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Chester pet 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: Bryan J.
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Bryan J.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Chester, MD, 21619

Bryan did an excellent job dropping in on our two elderly dogs and my cat 4x a day for three days. I highly recommend him. He followed my instructions with medications for my dogs precisely. Walked and spent time with them all and sent great pictures and reports daily. We are very pleased with Bryan’s outstanding care for our fur babies. I already rebooked with him for future dates.

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Joanna Z.
Sitter Profile Image: Bohdanna G.
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Bohdanna G.
from
$15
per visit
5.0 out of 5 stars
75 reviews
28 repeat clients
25 years of experience
Stevensville, MD, 21666

Bo is an excellent dogsitter for our three dogs. She comes by twice a week to let our dogs out while we are at work. She is reliable, thorough, communicative, responsible, and so loving to the dogs. We know they are in good hands with her and highly recommend her!

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Leah B.
Sitter Profile Image: Savannah T.
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Savannah T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
1 year of experience
Stevensville, MD, 21666

Savannah was so friendly and helpful. She handled everything how i would have. My boys are pretty emergentic and cuddly- she was able to really help me feel at ease while we were gone. She did a wonderful job and we will be using her again for sure!

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ruthie b.
Sitter Profile Image: Mary L.
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Mary L.
from
$25
per visit
4.9 out of 5 stars
35 reviews
15 repeat clients
30 years of experience
Stevensville, MD, 21666

Mary took wonderful care of my Kitty, Prim. Prim is usually a scaredy-cat and keeps her distance but came right out to Mary for cuddles. Great communication and updates. Will use again. Thank you Mary!

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Jenny H.
Sitter Profile Image: Jason & Tracy Y.
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Jason & Tracy Y.
from
$12
per visit
4.9 out of 5 stars
78 reviews
31 repeat clients
10 years of experience
Stevensville, MD, 21666

Jason and Tracy are awesome! Very thorough and follow your instructions exactly as you like….and my three pups love them after only 2 visits!! I highly recommend them!

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Wendy W.
Sitter Profile Image: Shannon M.
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Shannon M.
from
$20
per visit
4.6 out of 5 stars
5 reviews
9 years of experience
Stevensville, MD, 21666

Shannon was very attentive and reliable. I can see she is loving and caring from her daily visits, messages and photos shared!

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Lori B.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$25
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Chester, MD, 21619

Thank you Hannah for this trial run. Taking the time to get to know my boys & their schedules We are looking forward to our vacation now knowing they will be well taken care of while we are gone

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Julie B.
Sitter Profile Image: Jennifer M.
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Jennifer M.
from
$15
per visit
20 years of experience
Stevensville, MD, 21666

About: I have over 20 years of experience working with pets. I have worked as an emergency Vet tech assistant and as a boarding facility manager in the past. I love helping people in my community with their pet care needs while getting all the snuggles that I can! I have a very flexible schedule! I am a photographer part-time and am able to create my own schedule accordingly. I have such a passion for animals and love to help people! I treat all pets as if they were my own. I am dependable, respectful and trustworthy. I will do whatever I can to ensure that your pet(s) and their owners are happy!

Sitter Profile Image: Alexis B.
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Alexis B.
from
$16
per visit
5.0 out of 5 stars
1 review
12 years of experience
Grasonville, MD, 21638

About: I have always been an avid animal lover, and have been an active caretaker in my community. Dogs, cats, fish, you name it. I'm happy to take pets on runs/walks, make sure they get plenty of playtime and love, and treats too. I am mostly available on weekends, and occasionally weekdays, inquire and we can work something out together. But can often stop by to let a pet out during the day. I will follow whatever instructions you have and need for the best care of your animal. I will check in with you if you need me too, and make sure everything is done to your liking.

Sitter Profile Image: Kaileigh T.
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Kaileigh T.
from
$14
per visit
10 years of experience
Grasonville, MD, 21638

About: I’ve had dogs and cats growing up. I have always stepped up to take care of them when it comes to feeding, walking, bathing, etc. I am a full time 3rd grade teacher working in a near by county. I am available nights after 4:00pm and anytime on the weekends! I do not have a fenced yard but it is pretty big for a dog to roam around in. I have plenty of room in my house for the animal to be crated if needed. I also allow animals to be on furnitures and in bed. I am a big animal lover/cuddler. I have no issues with a dog who likes to cuddle, jump, etc.

Sitter Profile Image: Julie K.
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Julie K.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Chester, MD, 21619

She was amazing!! Super flexible with our crazy schedule!

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Jenna K.
Sitter Profile Image: Brooke F.
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Brooke F.
from
$25
per visit
5.0 out of 5 stars
76 reviews
17 repeat clients
10 years of experience
Chester, MD, 21619

I needed a last minute sitter just to stop at my house and feed my dog this last weekend (mind you- he’s a German Shephard/Lab- he’s a big boy!) breakfast and take him out to go potty. I have been hesitant to use a kennel, as my dog was severely bit a few months ago. So I turned to Rover- Brooke was luckily able to pick up the job at the last minute and help out! She met with me the day before, we video chatted and she was understanding of Ace’s routine and our home guidelines. She has tons of experience with dogs! I highly recommend Brooke & will be using her again!

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Chrissy L.
Sitter Profile Image: Lena M.
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Lena M.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
20 years of experience
Stevensville, MD, 21666

Lena was a calm, caring presence for my senior kitty -- just what he needed. I so appreciated her photos and videos as well. Will definitely use her again!

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Laura T.
Sitter Profile Image: Cristina M.
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Cristina M.
from
$30
per visit
5.0 out of 5 stars
9 reviews
25 years of experience
Stevensville, MD, 21666

Cristina is an excellent pet sitter! Our sweet kitty is in end stage cancer and Cristina took such great care of her, ensuring she got her shot and monitored her food/water intake to assure us that all was well while we were away. I would definitely hire Cristina again!

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Sue M.
Sitter Profile Image: Melanie P.
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Melanie P.
from
$20
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
30 years of experience
Grasonville, MD, 21638

Melanie is terrific. She was very caring and sweet with this tiny little shy and nervous dog. She was responsive reliable and pro.pt and sent reports regularly

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michael e.
Sitter Profile Image: Bhavani K.
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Bhavani K.
from
$35
per visit
5.0 out of 5 stars
18 reviews
2 repeat clients
15 years of experience
Chester, MD, 21619

About: All the dog owners I work with love the fact that I love their dogs like they are my babies. I walk them as well as give them cuddle time. Most dogs need cuddles and need to know you are around for them. I maintain a routine for them. I work from home so always around for them. Of course you will get pictures and little love notes from them when you are gone. I know you miss them and they miss you. I have rescued all my pets and worked thru a lot of issues. I have had a therapy dog and am working on my next therapy dog. I have also fostered pups and will continue fostering them. I always bring my dog when i am house sitting. If you have rules for your pets, I will implement them In your absence. I am quite comfortable with getting meds into them or subcu shots. I work from home which allows me to give them lot of attention. Not having a fenced yard means our day starts with a walk and ends with a walk. I take them on walks as they need to go out. I love going to parks with the fur babies for long walks. As a foster mom iam comfortable with dogs that need Meds or have needs.

Sitter Profile Image: Ryan L.
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Ryan L.
from
$25
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
25 years of experience
Annapolis, MD, 21409

About: I’ve been a lifelong "dog guy" and have spent years caring for the pets of friends, family, and neighbors. As the saying goes, "There are no strangers here; only dog friends you haven't yet met." I’m an expert at making dogs feel loved and secure while their parents are away. I find that exercise and companionship make for happier fur friends. I am a freelancer, which allows me to be very punctual and reliable for morning, mid-day check-ins, or afternoon walks. I understand how hard it is to leave your pet, so I like to send updates and fun photos so you never feel out of the loop. I’m happy to help with: *Standard neighborhood walks/jogs *Drop-in visits for potty breaks and playtime. *Feeding and refreshing water bowls. Attuned to dogs with diet restrictions *Transporting your four-legged loved one to parks (example: Greenbury Point, Quiet Waters Park) *Transporting to the groomer, vet appointments I treat every dog I care for as if they were my own. I'd love to meet you and your pup soon! I have great flexibility in the mornings and afternoons. Mon- Friday Morning: 5:00 am - 2:00 pm Evening: 3:30 pm-9:00 pm Saturday-Sunday 5:30 am - 9:00 pm Care in my home: I have a large fenced yard, great for playing catch, if you require morning or afternoon care away from your home. Care at your home, where most pups prefer, I can follow your family's routine: potty breaks, exercise level.

Sitter Profile Image: Carmel S.
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Carmel S.
from
$25
per visit
5.0 out of 5 stars
16 reviews
2 repeat clients
5 years of experience
Grasonville, MD, 21638

Excellent Job. Above and beyond.

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Mark K.
Sitter Profile Image: Hannah E.
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Hannah E.
from
$20
per visit
18 years of experience
Stevensville, MD, 21666

About: I have taken care of many kinda of animals since I have been young. My neighbors, family, and friends have relied on me to feed, walk, and care for their pets! I am a 3rd year PT student doing clinicals in Annapolis, MD. I have time after work to check in, hangout with, and/or walk your furry family members! I am very clean and love to keep my home and work space neat and tidy. While watching for pets I can provide light housekeeping to keep the home looking wonderful for the clients return!

Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
30 years of experience
Annapolis, MD, 21409

Tiffany was a real trouper to come visit our 3 month old puppy. She is knowledgeable, organized and loves dogs. Communicates promptly, and is open to changing circumstances. I highly recommend her.

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Shirley C.
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Over 69
pet parents in Chester have booked pet sitting

Chester pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

We just love savannah. We always know are dogs are loved and played with! We always recommend her to everyone we know! Shes the best. 🐾

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ruthie b.
Drop-In Visits
5.0 out of 5 stars

Allie was great and I'd definitely recommend her! I really appreciated her communication and how much she cared for my kitties.

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Tim
Drop-In Visits
5.0 out of 5 stars

I could tell you guys had good quality time Thanks so much Meanwhile Beans is doing very good & it was not cancer ❤️❤️❤️

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Julie B.
Drop-In Visits
5.0 out of 5 stars

Rebeka couldn’t be nicer and handled our handful of a dog very well. She responds to messages quickly, and I appreciated her reaching out to confirm the day of our scheduled appointment. She is very prompt and has a lot of dog behavioral experience that is helpful. I would not hesitate to use her again!

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

Loved MariAnn. She was prompt, professional, and took excellent care of our three fur babies. I would very much use her services again. Plus I loved the photos she sent.

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

Thank You Jackson, It is such a relief knowing the pets can stay in their own home and are well taken care of.

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

Stacey was so great taking care of our two kitties and watching over our home while we were away. She is just so wonderful and thoughtful and our cats love her! Always keeping us up to date on their daily activities and they got plenty of scratches and love from Stacey while we were away. She’s just the best!!

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

Sydney met with me and Jojo beforehand and then did a drop-in visit with Jojo. Jojo loved her visit. It was nice knowing I can count on Sydney while I am at work and I received a report card, pictures & a video! Thanks so much!

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

Our dog, Daisy, loved spending the day with Melanie. In fact, she didn’t want to go home at the end of the day. I also appreciated Melanie as a pet sitter.She was always communicative and easy going. Highly recommend!

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

Cristina is an excellent pet sitter! Our sweet kitty is in end stage cancer and Cristina took such great care of her, ensuring she got her shot and monitored her food/water intake to assure us that all was well while we were away. I would definitely hire Cristina again!

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

Lindsay is very friendly and took great care of our pet(s) plus did everything we asked and extra! Thank you so much! We would love to book again soon!

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Ashley R.
Drop-In Visits
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  1. 1. Search

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  3. 3. Book & Pay

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The median cost per night for pet sitting in Chester is $20

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    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Chester average 6
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

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

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

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

As of Jun 2026, there are 461 pet sitters in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 85% of Chester pet sitters respond in under an hour.

Pet sitters in Chester have an average of 11 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet 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 pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

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

There are 461 pet sitters in Chester on Rover, so you’re sure to find the perfect match for your pet! In Chester, 100% of pet sitters offer daily exercise, 100% offer medication administration, and 83% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

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

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