Pet Sitting in Chesapeake City

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 Chesapeake City pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Aleisha T.
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Aleisha T.
from
$20
per visit
5.0 out of 5 stars
4 reviews
5 repeat clients
15 years of experience
Chesapeake City, MD, 21915

Aleisha is so great! She took the time to meet our dogs ahead of time and get the lay of our house. She manages all 4 of our pups with ease! Our dogs range from puppy to senior, and she takes good care of all their individual needs. She is always on time and so flexible with our changing schedules. She communicates everything and takes the best pics during her visits! Book her now :)

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Erica W.
Sitter Profile Image: Christine S.
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Christine S.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
26 reviews
15 repeat clients
25 years of experience
Elkton, MD, 21921

Couldn’t be happier with Christine and how she took care of our three fur babies. Each one has a very unique personality and two out of three need to be won over which Christine did quickly. Her checks-ins were both full of information and very thoughtful with lots of pictures showing how well they were behaving while we were away. We will definitely use Christine again.

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Renae K.
Sitter Profile Image: Yvonne & Joseph K.
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Yvonne & Joseph K.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
188 reviews
46 repeat clients
50 years of experience
Newark, DE, 19702

Highly recommend booking with Yvonne. She is always on time. Takes great pictures of Ky. He enjoys hanging out with her and is always excited to see her arrive. Yvonne is very friendly and I never feel like I have to worry about Ky while he’s in her care!

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Leticia W.
Sitter Profile Image: Destiny P.
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Destiny P.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
105 reviews
21 repeat clients
10 years of experience
Bear, DE, 19701

Destiny is AMAZING! After having to cancel a horrible dog sitter she immediately stepped up to help. My dog absolutely loves her! She is a 10/10 and will always try to book with her first!

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D.j. W.
Sitter Profile Image: Nikkita J.
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Nikkita J.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
49 reviews
18 repeat clients
4 years of experience
Middletown, DE, 19709

Nikkita was perfect. We needed a walker same day with very little notice and she came through to walk our boy. She was very sweet and communicated everything with us. We would definitely use her again.

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Dan R.
Sitter Profile Image: Paul C.
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Paul C.
from
$20
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Elkton, MD, 21921

About: As dog owners, we understand how important it is to find someone trustworthy to care for your pets. We have two dogs and truly enjoy spending time with animals of all kinds. We know that pets are family, and we strive to provide dependable care and regular updates so you can have peace of mind. We look forward to meeting you and your furry family members! 🐾 I currently work in HVAC but there are 1-2 days a week I typically have off so on those days I would have a good amount of availability. Also have weekend availability and holiday. I don’t plan on transporting or bringing dogs to my house but I can do any care plan you would like at your house.

Sitter Profile Image: Tre S.
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Tre S.
from
$25
per visit
4.6 out of 5 stars
14 reviews
2 repeat clients
6 years of experience
Middletown, DE, 19709

Tre is on time and communicates all about the visit. He is extremely professional and easy to work with. Plus my dog did not bark at him!!! While my Bella has fears and anxiety issues, he found ways to work with her. We will definitely use him again!

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Judie B.
Sitter Profile Image: Stephanie J.
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Stephanie J.
from
$18
per visit
5.0 out of 5 stars
87 reviews
17 repeat clients
20 years of experience
Warwick, MD, 21912

So thankful for Stephanie! Even in the awful rain & wind, she took my puppy on a little walk so he could have an opportunity to stretch his legs because I work long hours. She’s the best!

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Emily C.
Sitter Profile Image: Breanna P.
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Breanna P.
from
$22
per visit
5.0 out of 5 stars
56 reviews
18 repeat clients
15 years of experience
Middletown, DE, 19709

Breanna and her pup Hannah helped keep our dogs company while we were away. Check-ins were always on time and the updates/photos were very appreciated.

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Brandon W.
Sitter Profile Image: Deanna C.
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Deanna C.
from
$10
per visit
20 years of experience
Bear, DE, 19701

About: Owning a Giant Breed can have its limitations when it comes to pet care, especially in a pinch. My experience & passion for larger breeds provides you with peace of mind that your family pet will have a safe and comfortable experience that caters to their size, energy levels and sometimes timid temperament and sensitive needs. My goal is to offer services that allow you a night out or vacay get away feeling guilt free & secure in the care that's being provided to your gentle giant fur baby. I am available late evenings on Monday & Tuesdays. I am currently available for dog walking or dog visits/drop ins on weekends. After the holiday season I will be offering boarding services 7 days a week. I have a 1 year old female English Lab. She is crate trained & also free roaming. She is off leash trained and always happy to have friends to play with! She also has been around senior/more timid dogs and respects their space and energy levels. Loves kids and all humans in general. We cant wait to meet your pup!

Sitter Profile Image: Randall D.
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Randall D.
from
$15
per visit
12 years of experience
Middletown, DE, 19709

About: As an engineer and proud owner of two large dogs, I bring attention to detail, and reliability to pet care. I am organized, observant, and proactive, ensuring every walk, meal, and play session is safe, structured, and enjoyable. With years of hands-on experience caring for my own dogs, I carefully observe behaviors, anticipate needs, and provide personalized love and attention, giving each pet a happy, and secure experience. I am a full-time Engineer working a 4-10 schedule where I am off 3 days per week. I have plenty of time to take care of pets during the weekends. I have 2 dogs that are extremely well behaved and friendly. They are both crate trained and love to play in the fenced in backyard.

Sitter Profile Image: Selena L.
Verified Enhanced Background Check
Selena L.
from
$19
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
El Cerritos, Bear, DE, 19701

Selena was amazing with Kyro and Apollo. She is kind and had great vibes.

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Aline G.
Sitter Profile Image: Reid C.
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Reid C.
Star Sitter
from
$62
per visit
5.0 out of 5 stars
65 reviews
18 repeat clients
24 years of experience
Glasgow, DE, 19702

Our 3rd time booking with Reid- great as always! Provided pictures and played with our dog outside! Will continue to book Reid whenever we need dog coverage!

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Kelly G.
Sitter Profile Image: Shawna B.
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Shawna B.
from
$20
per visit
15 years of experience
Elkton, MD, 21921

About: Hi! My name is Shawna, and I’m an animal lover! 🐾 I have a dog named Neeko who loves making new friends, and a cat named Fat Tee who keeps us entertained. I’ve been around animals my entire life and truly love them all. I am happy to take your pups for walks, play outside, or just stay home and provide plenty of cuddles and companionship. I understand that pets are family, and I will do my best to make sure your fur babies are happy, comfortable, and cared for as if they were my own! ❤️🐶🐱 I work full-time during the school year but am available evenings, weekends, holidays, and throughout the summer. I’ll make sure your pets get plenty of attention, exercise, and love while you’re away. Your pet’s safety and comfort are my top priorities. I will follow your pet’s routine, provide lots of attention, and make sure they feel secure and cared for whether I’m in your home or mine.

Sitter Profile Image: Whitney W.
Verified Enhanced Background Check
Whitney W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
5 reviews
4 repeat clients
10 years of experience
Newark, DE, 19711

About: Animals have been a part of my life for as long as I can remember. Growing up with dogs and cats, and now having two rescue dogs of my own, I just can't imagine life without them. I haven't used Rover before, but I've spent years watching friends' dogs and cats whenever they needed someone they could trust. I've raised puppies, cared for kittens, and even handled medications when needed, so I'm no stranger to what animals need to feel safe and loved. I come to your home so your babies can stay in their own space, in their own routine. Every animal is different and I take the time to get to know them. Big or small, they all get the same gentle, attentive care. I just genuinely love animals, and that's something you'll see the moment I meet your pet. I'm always happy to set up a meet-up before booking so we can connect, your pet can get comfortable with me, and we can make sure it feels like the right fit for everyone I recently graduated from Arcadia University with my Master's in Physician Assistant Studies. While I study for my boards and prepare to move back home to Washington, I have time on my hands and want to spend it doing something I truly enjoy. Right now my days are completely open, which means your dog gets my full attention. No rushing off, no squeezing them in between a busy schedule. I'm there as long as they need me. As the mom of two very needy rescue dogs, I completely understand wanting your babies to have someone around as much as possible, and right now, I'm in a position to give exactly that! Since I will be in your home, my first priority is to respect whatever routine and rules you have in place for your pet. I am happy to provide as much or as little entertainment, snuggles, or space as your fur baby needs. When it comes to walks, I'm no stranger to dogs that pull on the leash or get reactive around other dogs. I've handled strong, reactive animals before and I feel confident and calm managing them.

Sitter Profile Image: Brice B.
Verified Enhanced Background Check
Brice B.
from
$15
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
14 years of experience
Newark, DE, 19702

About: I’ve grown up in a home with dogs, and worked briefly in an animal shelter, caring for dogs from newborn puppies to seniors, responsible for their daily care and enrichment. My job ends at 3:30pm, allowing me flexibility in afternoons and evenings, while being totally free on weekends to tend to any dog or cat. As the seasons change, so do my hours, allowing me more availability for bookings. I have knowledge on animal enrichment and training, and know how to handle different pets with all different temperaments. I know how to crate dogs, walk them, and bond with all sorts of dogs and cats.

Sitter Profile Image: Raven C.
Verified Enhanced Background Check
Raven C.
from
$22
per visit
5.0 out of 5 stars
4 reviews
3 repeat clients
13 years of experience
Bear, DE, 19701

Raven was wonderful!! She took excellent care of my two cats! We will definitely be booking her in the future

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Elizabeth E.
Sitter Profile Image: Lillian S.
Verified Background Check
Lillian S.
from
$30
per visit
4.9 out of 5 stars
38 reviews
17 repeat clients
25 years of experience
Elkton, MD, 21921

Lillian was awesome looking after our old cat. I told her our cat was old and small and would probably hide for all the visits. But she just loved Lillian! Came out each time, sat in her lap and got lots of ear rubs. Litter and food areas were cleaned well also. Thanks!

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Andrew B.
Sitter Profile Image: Jenna B.
Verified Enhanced Background Check
Jenna B.
from
$20
per visit
5.0 out of 5 stars
130 reviews
21 repeat clients
20 years of experience
Bear, DE, 19701

Jenna took amazing care of my two kitties and my fish! One of my cats (Bennie) likes to hide under the covers, she took a photo of him there and spent time with him where he was comfortable. Every day Bennie came out a little more! Peaches liked Jenna immediately too. I also loved how descriptive the updates were. I came home to two happy and well taken care of kitties :)

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Alex D.
Sitter Profile Image: Jen P.
Verified Enhanced Background Check
Jen P.
Star Sitter
from
$45
per visit
5.0 out of 5 stars
76 reviews
22 repeat clients
25 years of experience
Middletown, DE, 19709

Jen is absolutely the BEST petsitter you will ever experience. My cat is very high maintenance with her attitude and her massive hair (forest cat). Upon my arrival home kitty was calm, very content , and had an extensive grooming! My home was exceptionally clean with the removal of litter and cat food cans. Jen met me before the sitting dates and she was extremely knowledgeable . She has tons of common sense--- You will not need to give her pages of instruction. She GETS IT ! In addition, my plants were watered during this 94 degree weather , mail was placed neatly inside, and trash cans were taken to the curb . Photos are sent to you at each visit. Love Jen to take care of my cat.

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Jane E.
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Over 35
pet parents in Chesapeake City have booked pet sitting

Chesapeake City pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Aleisha did a great job taking care of our 4 dogs. There are varying needs from care for an aging dog to younger energetic ones. They all seemed very happy.

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Kathryn H.
Drop-In Visits
5.0 out of 5 stars

Aleisha is so great! She took the time to meet our dogs ahead of time and get the lay of our house. She manages all 4 of our pups with ease! Our dogs range from puppy to senior, and she takes good care of all their individual needs. She is always on time and so flexible with our changing schedules. She communicates everything and takes the best pics during her visits! Book her now :)

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Erica W.
Drop-In Visits
1 / 1
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 pet 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.

Sitters in Chesapeake City 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 Chesapeake City 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 Chesapeake City 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 1,916 pet sitters in Chesapeake City. 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, 88% of Chesapeake City pet sitters respond in under an hour.

Pet sitters in Chesapeake City have an average of 17 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 Chesapeake City.

Rover makes it easy to find Chesapeake City 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 1,916 pet sitters in Chesapeake City on Rover, so you’re sure to find the perfect match for your pet! In Chesapeake City, 94% of pet sitters offer daily exercise, 95% offer medication administration, and 94% 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.