House Sitting in Chesapeake City

Find a loving house sitter to watch over your pets and your home.

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Chesapeake City house sitters

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

1 / 1
Sitter Profile Image: Christine S.
Verified Enhanced Background Check
Christine S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
15 reviews
9 repeat clients
25 years of experience
Elkton, MD, 21921

Christine was exceptional and took such great care of our home and our pup. She provided frequent updates with photos and videos. We scheduled last minute so finding such great care was a huge relief for us. Would recommend her and use her again in the future.

Profile image
Tim F.
Sitter Profile Image: Lacey S.
Verified Enhanced Background Check
Lacey S.
Star Sitter
from
$45
per night
4.9 out of 5 stars
7 reviews
4 repeat clients
10 years of experience
North East, MD, 21901

Lacey is so sweet and so loving. And she is so reliable and responsible!! Our family and our dog love her!!

Profile image
Jenel P.
Sitter Profile Image: Tre S.
Verified Enhanced Background Check
Tre S.
from
$60
per night
4.6 out of 5 stars
14 reviews
2 repeat clients
6 years of experience
Middletown, DE, 19709

We loved Tre! From the minute he pulled into the driveway, we felt comfortable that he would be a great fit to care for our enthusiastic pittie mix. He asked pertinent questions and took detailed notes during the meet and greet. Our dog responded so favorably to him and the became fast friends. We highly recommend him and will definitely be working together in the future.

Profile image
Alissa M.
Sitter Profile Image: Reid C.
Verified Enhanced Background Check
Reid C.
from
$85
per night
5.0 out of 5 stars
61 reviews
18 repeat clients
24 years of experience
Glasgow, DE, 19702

Reid is always great with our dog Lando! I continue to rebook anytime we need dog coverage! He provides excellent communication and pictures/videos of Lando while we’re away. Eases some of the stress of leaving our fur baby!

Profile image
Kelly G.
Sitter Profile Image: Rackeem R.
Verified Enhanced Background Check
Rackeem R.
from
$56
per night
5.0 out of 5 stars
23 reviews
10 repeat clients
7 years of experience
Middletown, DE, 19709

About: With over six and a half years of hands-on pet care, I bring a rare blend of experience, attentiveness, and heart. I’ve worked with dogs of all sizes, temperaments, and ages—from energetic puppies learning the ropes to senior pets needing gentle, attentive care. What truly sets me apart is my ability to read and respond to animals’ unique personalities. I create a calm, consistent environment where pets feel safe, loved, and understood. Whether it’s administering medication, offering leash training for puppies, or providing low-stress companionship for older pets, I bring patience and skill to every interaction. I also have experience caring for a diverse range of animals beyond just dogs and cats. From chickens and birds to hamsters and other small pets, I understand that every species has its own rhythm, needs, and comfort cues. I’m confident and compassionate with unique, exotic, or less-common animals, always prioritizing their safety, emotional well-being, and daily routines. Pet care is a built-in part of my weekly life. I’m highly flexible and genuinely enjoy working around each pet’s needs and schedule. Whether it’s early mornings, midday visits, evenings, or even late nights, I’m available and committed to making your pet’s care seamless and stress-free. I’m also happy to accommodate weekend bookings and unique timing requests whenever possible—just let me know what works best for you and your pet, and I’ll do my best to make it happen. Reliability, consistency, and clear communication are at the heart of everything I do. In clients’ homes, I prioritize maintaining their pet’s normal routine and environment. I follow all instructions closely—feeding schedules, walking routes, medication routines, and preferred playtime activities—so your pet experiences as little disruption as possible. I also make sure the space stays tidy and respected while I’m there. If I’m hosting pets in my home, I provide a calm, safe, and welcoming space. I separate animals as needed, keep food and water fresh and clean, and ensure they have access to cozy rest areas and supervised play. I never leave pets unattended, and I’m mindful of their comfort, especially in a new setting. In both cases, I focus on creating a low-stress, high-trust atmosphere, and I keep pet parents updated with messages, photos, and honest communication throughout the stay.

Sitter Profile Image: Aubrey D.
Verified Enhanced Background Check
Aubrey D.
from
$50
per night
5 years of experience
Elkton, MD, 21921

About: I have grown up with all kinds of animals and I love caring for all animals. I have also done a lot of dog sitting and care greatly for animals as if they are my own. I have cared for animals of all ages including older dogs that need medication. I work part time and go to school but I have a flexible schedule. I have a car that’s good on gas so distance is not an issue! When caring for someone else’s pet I make sure to give my full attention to the animal and do all I can to make sure the pet is well taken care of.

Sitter Profile Image: Meghan E.
Verified Enhanced Background Check
Meghan E.
from
$50
per night
20 years of experience
Bear, DE, 19701

About: Need someone who can handle more than just a walk in the park? I was raised on a farm and have professional zoo experience. I have cared for many animals and can administer meds, handle large breeds and provide loving care. Currently a dog and turtle owner, I am a responsible professional looking to help you enjoy your travels worry-free. I am available anytime on weekends. During the week, I can provide care in the early mornings before 8:00 AM and in the evenings after 5:00 PM. My goal is to keep your pet’s routine as consistent as possible while you are away. Drawing on my background in zoo and farm care, I am meticulous about following instruction whether that involves administering medication, adhering to strict feeding schedules, or managing specific turnout times. Because I work full-time, I structure my care around a schedule during the week: I provide quality care, exercise, and feeding before 8:00 AM and after 5:00 PM, while weekends are open for longer adventures and companionship. I treat your home with the same respect as your animals. I am experienced in maintaining a clean environment and can provide regular photo updates so you can enjoy your own adventures knowing your home and pets are secure.

Sitter Profile Image: Erica M.
Verified Enhanced Background Check
Erica M.
from
$55
per night
5.0 out of 5 stars
37 reviews
7 repeat clients
20 years of experience
Havre de Grace, MD, 21078

Erica was amazing! She kept us updated with photos and took such great care of our dog. We were so lucky to have her and will definitely be recommending her to all our family and friends!

Profile image
Amanda R.
Sitter Profile Image: Michaela A.
Verified Enhanced Background Check
Michaela A.
Star Sitter
from
$80
per night
5.0 out of 5 stars
52 reviews
13 repeat clients
17 years of experience
Bear, DE, 19701

We loved having Michaela watch our crew while we were gone! She provided regular updates, and was great handling our pets with special needs. Our house was spotless when we arrived home - we really appreciate the level of care she provided. We will absolutely be hoping to have her back when we travel in the future!

Profile image
Lex L.
Sitter Profile Image: Jennifer M.
Verified Enhanced Background Check
Jennifer M.
from
$50
per night
25 years of experience
Middletown, DE, 19709

About: I've had cats and dogs my whole life and have spent most of my adult life volunteering for 2 animal rescue organizations. I fostered over 170 cats for my last organization (that was over a period of 15 years!) caring for all ages as well as taking in some with medical needs. I'm skilled at administering medications of all sorts and we currently have an asthmatic cat that takes an inhaler. I've been a "cat person" my whole life, but love dogs too! My husband and I love the large breeds, in particular Mastiffs. We currently have 3 cats plus a Mastiff who is the biggest baby. :-) We recently moved to Delaware (from just outside of DC) and I'm looking to re-start pet sitting as I LOVE meeting new furbabies and taking care of them. I used to pet sit in VA but put it to the side when fostering took up most of my free time. I recently took an early retirement and have plenty of free time so can offer flexibility. Since I'm married my husband helps takes care of our own cats/dog, and he understands my love of animals and desire to help others. I understand that every cat/dog is unique, with their own personality and needs. I will take the time to get to know each one and tailor my approach to ensure their comfort level,

Sitter Profile Image: Jenni L.
Verified Background Check
Jenni L.
Star Sitter
from
$75
per night
5.0 out of 5 stars
154 reviews
65 repeat clients
15 years of experience
Newark, DE, 19711

Had Jenni watch my 2 dogs while I took a 4 day trip. Came home to everything being in order and the dogs were great! Will certainly hire again!

Profile image
Robert K.
Sitter Profile Image: Brice B.
Verified Enhanced Background Check
Brice B.
from
$50
per night
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: Jonaika W.
Verified Enhanced Background Check
Jonaika W.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
5 years of experience
Newark, DE, 19702

Jonaika is a mature, kind, responsible and communicative young woman. She stayed in our home with our two dogs for a holiday week, and provided loving and consistent care. She has a warm temperament which dogs loved, flows instructions, and cares for pets with great accountability. I highly recommend Jonaika for any pet sitting situation.

Profile image
Ashley A.
Sitter Profile Image: Jen P.
Verified Enhanced Background Check
Jen P.
from
$85
per night
5.0 out of 5 stars
71 reviews
21 repeat clients
25 years of experience
Middletown, DE, 19709

About: From caring for 10 senior dogs at a rescue, to bathing dogs that got sprayed by skunks, to training and taking dogs on their own outings to parks and nature hikes, you name it I’ve done it! Even flying with dogs! ✈️ I have experience with all breeds, ages, and like to keep pet parents informed with notes & pics. Growing up in farm country taught me to love and care for all animals, but dogs and cats are by far my favorite. I also have experience in administering medications to our furry friends. I left my career of being a nanny in CA to move to the east coast to marry my husband. That was 2019, and I’ve been boarding/caring for animals since then. I’m currently a stay-at-home wifey so the dogs get 100 percent of my attention when they are with us. We live in a 3 story townhouse with a small unfenced yard in front of our home, to a large grassy area on the side of our home, to a giant green grass patch directly behind us just out our back door. The neighborhood is VERY dog-friendly with lots of sidewalks and comes complete with a dog park in walking distance. Our home is dog-friendly meaning dogs are allowed on all furniture and we even have doggie steps for little pooches to get up on our bed if they wish. We also have a 2mile + walking path near us. So we have plenty of activity options. We even have Pluto cartoons for your pet to watch! Pets get 100 percent of my attention when they stay with us. Their comfort and safety is my priority as I do pet care full-time. Our home has no place that’s off limits to your pets. If they want to snuggle on our bed or relax on our couch or even be in our guest room - they are more than welcome wherever they are most comfortable. We even have a massive bean bag most animals love thinking it’s a giant dog bed 😂.

Sitter Profile Image: Cassidy L.
Verified Enhanced Background Check
Cassidy L.
from
$55
per night
4.5 out of 5 stars
8 reviews
4 repeat clients
5 years of experience
Bear, DE, 19701

She was excellent, took great care of my dogs and even Made sure my house was clean when I came home. My Puppies loved her and she sent some most appreciated Pics and videos of the puppies!! Definitely recommend her For anyone who needs a sitter!!

Profile image
Erin M.
Sitter Profile Image: Brenda G.
Verified Enhanced Background Check
Brenda G.
from
$35
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Newark, DE, 19702

About: With a lifelong passion for pets, I offer more than just care. I provide a loving, safe, and fun environment for your furry family members. I'm dedicated to their happiness and well-being, treating every animal with the same love and attention I give my own. You can trust that your pet is in the best possible hands. Because I run my own business and set my own hours, my schedule is flexible and can easily adapt to your pet's needs. Whether it's an early morning walk, a midday visit, or a late-night check-in, I can provide consistent, reliable care whenever your fur baby needs it. While you're away, I'll provide your pet with personalized care in the comfort and familiarity of their own home. This includes following their usual routine for feeding, walks, and playtime, ensuring they feel safe, happy, and loved. I'll also provide videos or pictures so you can have peace of mind knowing your furry family member is well-cared for.

Sitter Profile Image: Ciara A.
Verified Enhanced Background Check
Ciara A.
from
$25
per night
4.0 out of 5 stars
6 reviews
8 years of experience
Middletown, DE, 19709

We were nervous about leaving our senior cat with multiple health issues with anyone, but after reading Ciara’s profile and meeting her with Walter, we left him and our home in her care. She handled everything exactly as we hoped, followed instructions exactly, and kept us informed every day. She stayed until we returned, and the house was perfect. Walter was content, calm and happy.

Profile image
Judy A.
Sitter Profile Image: Delaney G.
Verified Enhanced Background Check
Delaney G.
from
$55
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
9 years of experience
Townsend, DE, 19734

Delaney is professional, reliable, and a great person. I wouldn't hesitate to recommend her and trust her completely with my most precious family members.

Profile image
Brian B.
Sitter Profile Image: Dalynn R.
Verified Enhanced Background Check
Dalynn R.
from
$32
per night
5 years of experience
Bear, DE, 19701

About: I grew up taking care of animals small and large and different species! I’m also a certified animal groomer and i am a huge animal lover! I’m currently working part time at a grocery store but i have a very flexible schedule and will always make time to see any animals! I always like to send photos or videos of the pets i’m taking care of so their mom or dad feels more comfortable seeing that their pup is having a great time!

Sitter Profile Image: Terry C.
Verified Enhanced Background Check
Terry C.
from
$75
per night
5.0 out of 5 stars
72 reviews
24 repeat clients
15 years of experience
New Castle, DE, 19720

Terry was absolutely Amazing!! She took great care of our 2 fur babies, sending photos and videos daily to update us on how they were doing while we were away. I was very anxious to leave our 2 cats with someone new, as our previous pet/house sitter is no longer in the business and we had not used someone new in many years, I have put off traveling due to this, much to my husband's dismay. I can say I was so relieved while away to see how great Terry was with our pets. I also think when we got home our house was cleaner than when we left! Terry did a fabulous job, she went above and beyond and now I'm ready to travel more feeling comfortable that we have found our new pet caretaker! I cannot recommend her enough!!

Profile image
Judy M.
1 / 1
View more sitters

Over 7
pet parents in Chesapeake City have booked house sitting

Chesapeake City pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Sydney is so kind, compassionate, and loving to our Tulio, Dana and to Izzabella. She truly loves her job and her 'clients'. We are new to the area and needed a pet sitter. So glad we found her!"

Profile image
Eileen B.
House Sitting
5.0 out of 5 stars

Fiona was awesome with our dog Dylan. She did a meet and greet a week before and then watched him for the weekend while we were away. She kept us updated with photos and letting us know how he was doing, which was awesome and when we got home, he seemed like a happy pup. Fiona kept our house clean and Dylan happy and loved while we were away. Can’t recommend her enough!

Profile image
Katherine O.
House Sitting
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house 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 house and 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 house sitting in Chesapeake City is $50

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 house 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 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chesapeake City on Rover as of Mar 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

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

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

As of Mar 2026, there are 623 house sitters in Chesapeake City. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

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

House sitters in Chesapeake City have an average of 16 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Chesapeake City.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chesapeake City house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.