Pet Sitting 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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Over 48
pet parents in Chesapeake City have booked pet sitting

Chesapeake City, Find top rated pet 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: 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: Yvonne & Joseph K.
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Yvonne & Joseph K.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
190 reviews
47 repeat clients
50 years of experience
Newark, DE, 19702

Kyrie absolutely LOVED having Yvonne here with him. He was trying to follow her out the door when she left! Yvonne is very nice. Very professional. Made sure to check with me in his feeding, bathroom, and treats. I love the pictures she took of Kyrie and I know Ky loved the belly rubs. So thrilled to have found Yvonne and have her watch Ky for me.

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Leticia W.
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: Sydney W.
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Sydney W.
from
$35
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
6 years of experience
Chesapeake city, MD, 21915

About: I grew up on a farm and have taken care of all sorts of animals including dogs, cats, farm animals and reptiles. I currently work as a Doggy Daycare Attendant and am a second year student at SUNY Delhi working on my associates in animal science. I work at a Dog Training facility as the Kennel Tech/Daycare Attendant from 6:30am-2:30pm on Tuesdays and 7am-1pm Wednesday-Saturday. I am willing to stay the night with your pet and can be there before and immediately after work! I can give proper care to any animal you need as well as play time, attention, and activity. I also have the skills to take care of animals with any medical needs/conditions.

Sitter Profile Image: Courtney B.
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Courtney B.
from
$20
per visit
10 years of experience
Bear, DE, 19701

About: I’ve grown up with dogs my whole life. I adopted a cat two years ago & can confidently say I now know the difference between how to interact with both. My friends call me the cat whisperer & I’ve watched both cats & dogs before. I am available to pet sit weekdays. My availability does depend on the week- I work remote so I am more flexible. I will try to keep my posted schedule as up to date as possible. I care for every pet with compassion & love. I understand that every dog/cat is different & needs to be treated accordingly. I get the importance of knowing your pet is safely looked after & treat them like my own.

Sitter Profile Image: Christine S.
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Christine S.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
27 reviews
16 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: Nikkita J.
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Nikkita J.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
50 reviews
19 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: Destiny P.
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Destiny P.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
106 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: Paul C.
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Paul C.
from
$20
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Elkton, MD, 21921

Love the photos! This was our first time using anyone for a pop in visit. This was totally last minute! Asked Paul and his fiance last night at 7pm to please help us, and without hesitation they came right over and met our boys. They did a pop in visit today and they were wonderful!!! Will definitely use them again :) They were great!!!! Thank you both so much !

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Leanna
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

Stephanie was amazing! I had an emergency and she was able to help with only a few hours notice. She sent lots of pics so I could see the babies, gave them love and treats, and basically provided much needed peace of mind. I will definitely use her again!

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Alison a.
Sitter Profile Image: Kristin Z.
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Kristin Z.
from
$23
per visit
29 years of experience
Bear, DE, 19701

About: At the age of 12 I was caring for animals working on a farm for a traveling petting zoo. I also had cats and dogs at home. In my 20's I volunteered at a local shelter where I adopted my first Pittie. I now have two Bulldogs a mom and son duo and a Fiesty but loving Sphynx Cat. I have availability early morning, during lunch , after 5pm , and before bed time Monday through Friday. On Weekends my time is more flexible I will treat your animals no different then I treat my own. They will be my buddies during your time away. I will send photos and updates each night.

Sitter Profile Image: Brittany F.
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Brittany F.
from
$15
per visit
5.0 out of 5 stars
3 reviews
20 years of experience
Warwick, MD, 21912

About: My farm is a beautiful sanctuary that we love to share with all furry friends! Whether they want to splash in the pool, run outside in a safe CLEAN secure area, or just have a nice snuggle in their indoor kennel or maybe even stretch out on the couch- just know they’ll be wagging to come back! I have 6 horses on the property, 13 chickens, 2 turkeys, 2 outdoor barn cats, and my Friendly Laid back dog Archie. I provide love & care which is more important than anything else. But of course- I follow parents rules! My entire life revolves around my farm and caring for all of my animals. I am on the property 24/7 as this is my full time job. And luckily it’s my passion. We have a beautiful fenced in pasture with lots of space to run. We are in a very private and rural area. We also have a pool- only if parents are OK and the Pup chooses to take a dip! Your Pup will always be supervised. If there are restrictions we will always abide by them. We also have dog crates if needed or requested and a beautiful inside area as well. Basically your Pup is gonna have free range and feel a home away from home.

Sitter Profile Image: Brice B.
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Brice B.
from
$15
per visit
5.0 out of 5 stars
6 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 shifts are short consistent, allowing me to have a concrete schedule to work around to best meet the needs of all dogs and cats. 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: 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: 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: Lillian S.
Verified Background Check
Lillian S.
Star Sitter
from
$30
per visit
4.9 out of 5 stars
38 reviews
17 repeat clients
25 years of experience
Elkton, MD, 21921

Both our dogs liked Lillian from the first meeting, and that helped us dog parents deal with our separation anxiety. Lillian was always prompt to arrive at the appointed times. Our dogs were healthy and happy when we got home. We’ll ask for Lillian by name next time!

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Adriane M.
Sitter Profile Image: Reid C.
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Reid C.
Star Sitter
from
$62
per visit
5.0 out of 5 stars
67 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: Jenna B.
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Jenna B.
from
$20
per visit
5.0 out of 5 stars
131 reviews
21 repeat clients
20 years of experience
Bear, DE, 19701

Jenna was consistent in her stops to care for our cats, went above and beyond in making time to play with them and be present in our absence, and showed an immense amount of love for them although only being with them for a week. Beyond that, our traditionally shy cat immediately took to her and trusted her in a much shorter amount of time than seen otherwise with previous guests. Jenna's statuses were always detailed and there were PLENTY of pictures for us to comb through after every visit. Choose Jenna to care for your pets - You won't regret it!

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Hayden S.
Sitter Profile Image: Nancy L.
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Nancy L.
from
$25
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
12 years of experience
Newark, DE, 19702

About: I’ve spent years caring for and training dogs, including raising and training four Australian Cattle Dogs—a breed known for its intelligence and high energy. Through that experience, I’ve learned how to read canine body language, reinforce good behaviors, and confidently handle dogs with different personalities and energy levels. I’ve also walked dogs for several of my mom’s clients throughout the Hockessin and Wilmington area. My focus is on providing safe, reliable, and personalized care while treating every dog as if they were my own. I am home full-time, which allows me to provide attentive, personalized care throughout the day. Your dog won’t be left alone for long periods and will receive plenty of potty breaks, exercise, playtime, enrichment, and affection. Being home full-time also allows me to closely monitor each dog’s well-being, maintain their routine, and ensure they feel safe, comfortable, and loved while you’re away. Your dog will be cared for like one of my own in a safe, loving home environment. I have a fully fenced 0.6-acre yard where dogs can safely run, play, and explore under supervision. They’ll also have the companionship of my three friendly, well-socialized dogs if they enjoy being around other dogs. Throughout the day, your pet will receive plenty of exercise, potty breaks, playtime, enrichment, and affection. I follow each dog’s routine as closely as possible, including feeding schedules, medications, and any special instructions, so they feel comfortable, happy, and at home while you’re away.

Sitter Profile Image: Shirl B.
Verified Enhanced Background Check
Shirl B.
from
$20
per visit
5.0 out of 5 stars
22 reviews
7 repeat clients
12 years of experience
Elkton, MD, 21921

Finding Shirl for our Zoey, has been the absolute best thing for Zoey and for us as well. The care she gives is more than that, Shirl has also become a favorite loving human for Zoe. We had to go out of town and had her do multiple drop ins and it went amazing? Zoey was able to stay in the comfort of her own home, had no accidents, enjoyed each visit with Shirl and was so happy to greet us when we got home. There's no doubt Shirl is great with animals, but also gives them so much love that they thrive and totally enjoy her company. She is the Best of the Best and we would recomend her and Rover to anyone!!! ~Danny & Lyndi~

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Lyndi D.
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The median cost per visit for pet sitting in Chesapeake City is $20

Pet parents share their Rover experiences - Chesapeake City

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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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Chesapeake City average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Chesapeake City

Frequently asked questions about Rover

The average cost for Pet Sitting in Chesapeake City on Rover is $18.32 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 Pet 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 Pet Sitting. For more information on service fees, click here .

As of July 2026, there are 1,967 sitters on Rover offering Pet Sitting across Chesapeake City. 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 Chesapeake City 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.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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.

Yes, you can find sitters who have experience with handling special pet needs in Chesapeake City. On Rover:

  • 94% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 94% 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.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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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