House Sitting Chesapeake City
Find a loving house sitter to watch over your pets and your home.
Chesapeake City, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“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.”
“Sidney was amazing and so attentive to max and cookie. She was oving with them and kept us updated. Our babies fell in love with her instantly. She's officially a part of the family definitely our go to.”
“Reid is fabulous! It was evident that he cared tremendously for my pets. Reid far exceeded our expectations and I would highly, highly recommend him for all of your pet sitting needs.”
“Jenni and Matt were absolutely wonderful with our pack! They were incredibly patient, attentive, and caring every step of the way. We are so grateful they were available and able to take great care of our pets while we went on vacation. We highly recommend them, they’re a fantastic team!”
“Tre has a calm demeanor & is very professional. He came over prior to house sitting to meet our dog, who took to him immediately. He followed our schedule, took him for long walks and when we came home our dog was well adjusted and comforted. Thank you, Tre for a job well done!”
“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.”
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.
“Definitely took care of my fur babies they were not anxious when I got back home which is a relief. I only critic would be of the amount of times my door alerted me of in and out home alerts (not ones of taking out trash which makes me anxious) and would like more photos next time. But other than that kitty care 10/10. And like I said next time as in, I would have her take care of my babies again!💕 very sweet lady. Very responsive. And knows what’s she is doing.”
“Michaela was fantastic! Sent plenty of photos and updates throughout the stay and we felt so reassured knowing she was taking such good care of our dogs. House was so clean and pups were happy!”
“Rebecca did an excellent job staying at our home with Pippin! She was really prepared with questions to help the weekend good smoothly and to understand his needs. She was very responsive to messages and sent detailed updates and pics. Our pup had a great time!”
“I was going to be away on a 15 day vacation in Europe and concerned I wouldn’t be able to find a someone I could trust to care for my two young cats for such a long time. Any and all worries melted away when I met Jen! She is very personable, very reliable and caring. Jen sent me daily updates on my kitties interactions with her and lots of photos . I highly recommend her to care for your pet. I will definitely continue with Jen for taking care of my fur babies 😊”
“Nina did an excellent job taking care of our puppy. We got him last week and were so nervous to leave him alone. She gave us updates, sent us pics, got back to us within minutes, followed all instructions we asked of her, and ensured his safety. My puppy is sooo shy with other people, and he went right to her. 10/10, will book for the future!!!:)”
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.
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.
About: I’ve spent my entire life living with cats and caring for them. I also spent last year living with a service dog in training and caring for him I currently have an internship at UD throughout the summer. I am available both before work and after work to care for pets. I can provide walking, feeding, playing, and just company for animals. I I will give your pets my full attention, spend time with them, and care for them however they may need. I will make sure the pets are in fantastic care.
About: Although my family has never owned a dog, I have always loved taking care of my aunts, neighbors, and family friends dogs. I always make sure to pay attention to detail when watching a dog and meet each dogs needs whether that be a walk, playing with a toy, belly rubs, or even just relaxing. As a part-time graduate student at USM, I will have time during the day for a dog walk, or to check-in on your pup! I will be available on most weekends for house and dog sitting. I am available to come to your dog and stay with him/her so they do not have to move out of their comfortable environment and stay at a new space with new people.
“Terry is consistently excellent! She always leaves our home better than she found it and takes good care of our boy. She provides thorough updates, it’s so nice to be able to travel and not worry about our dog or our home. Couldn’t ask for more!”
About: I have helped care for my family’s dogs and cats since I was a little girl, and my love of animals has grown deeper into my adulthood. I have experience training puppies basic obedience commands, and I have a passion for learning and understanding all different types of animals. I am excited for the opportunity to care for your family’s pets! I am a full-time special education teacher, so I am available and ready to play with and assist your pets in the evenings on weekdays and any time on weekends. You can count on me to create a caring, positive environment for your pet. I am comfortable and willing to provide your pet with food and water, exercise/walking, cuddles, playtime, and more! I am happy to fulfill all of your requests when it comes to caring for your pet.
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 😂.
The median cost per night for house sitting in Chesapeake City is $50
Pet parents share their Rover experiences - Chesapeake City
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Chesapeake City sitters!Sitters in Chesapeake City average 4 repeat house sitting clients
FAQs for House Sitting - Chesapeake City
Frequently asked questions about Rover
As of July 2026, there are 1,115 sitters on Rover offering House Sitting across Chesapeake City. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Chesapeake City walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Chesapeake City maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Chesapeake City choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
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.
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 .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
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.
Yes, you can find sitters who have experience with handling special pet needs in Chesapeake City. On Rover:
- 97% 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.
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