Dog Sitting Chesapeake
Book a Chesapeake dog sitter to watch your dog in your sitter’s home or yours.
Over 1,323 pet parents in Chesapeake have booked dog sitting
Chesapeake, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“She was so great with my dog and I scheduled her very last minute and she was able to work me in! I appreciate her greatly and she took great care of my dog and my home! Thank you again!!!”
About: I have been around dogs since I was about 8 years old and have experience with both small and large breeds. I have owned 4 dogs myself and caring for dogs has always been something I genuinely enjoy. Over the years, I have gained experience with dogs of different ages, sizes, breeds, energy levels, and personalities. I understand that every dog has unique needs and routines, whether that means lots of playtime and exercise or a calmer, more relaxed environment. I am comfortable with feeding schedules, walks, basic care routines, and giving dogs the attention and patience they deserve while their owners are away. As a pet owner myself, I know how important it is to trust the person caring for your pets. I will always treat your dogs like my own and provide reliable, loving, and attentive care. I’m currently working a flexible schedule and I am most consistently available in the afternoon and evening times during the weekdays and fully on the weekends to provide extra time for your animals! I have a fully fenced yard and the space/ability to crate as needed. I do currently have 2 friendly cats in home who are used to other cats/dogs. Each member of my household has experience with cats and dogs and would be excited to show yours some love and attention up close or far away! I always prioritize creating a safe, calm, and comfortable environment for every pet in my care. I understand that every animal has different needs and personalities, so I take the time to learn their routines, preferences, and comfort levels whether inside your home or mine.
About: I’ve been taking care of dogs since I was 11. I recently had to let my two girls go, so I’m looking forward to loving on your babies. I have experience with puppies all the way to senior dogs. Both of my girls needed medication towards the end, so I’m familiar with administering pills on a schedule and anything else that goes with owning a senior dog. My oldest had dementia, so if your pup has that, I can handle the quirks that come with that. I’ve also watched my friends bigger dogs, and they love just as much cuddles as the little ones do. Taking your fur baby out for walks, cuddling with them, and playing with their favorite toys would bring so much joy. You’ll have peace of mind (and updates) if you let me take care of them like you would. I am a teacher, so during the weekends and summer I have all the time to spoil your precious baby. Being a teacher also means I can spend extended time with your pet during the summer. I’m very good at following schedules and routines to help make your pet feel as comfortable as possible while you’re away. I will love on them, play with them, and do anything else you need so both of you feel relaxed while you’re at work or on a trip.
“This is the first time that I’ve used any kind of application like this, and I have to say that Casey was amazing. My pet gets nervous around strangers, and she came to house to meet him first so he would be comfortable. That indicated to me that she handles the visits as she would want for her own pets. She also had wonderful communication, and very accommodating during the entire time she was there. I am so glad that I have found someone that I can trust to take care of my pets when needed. I highly recommend her, and will be using her again in the future.”
About: I started working as a vet tech at 17 and have two years of boarding experience at a veterinary hospital, well versed in schedules and procedures including medication and special needs. Currently working but flexible schedule, willing to work with your needs! Older/less active dogs preferred but happy to play with a puppy when so necessary. I worked directly beneath the boarding manager and trained new staff in observation, care schedules, and proper safety protocols. I also form bonds of trust with any animal I’m working with to ensure their and my comfort.
“Updated me everytime he checked in on my kitty and was in touch the entire time. Couldn’t have asked for a better sitter for her first time being left alone”
“Hannah did a great job taking care of our puppy during drop-in visits! She gave us plenty of pictures on our updates and I could tell our puppy was having a blast. She has also last-minute helped with our puppy when our regular sitter, her sister, has had anything come up. Really appreciate her and would recommend!!”
“Highly recommend! At the meet and greet she was so easy to talk to and our dog Luna loved her! While we were away I didnt worry if callie and luna were taken care of, she sent pictures of them getting all the love and attention. I think our house was cleaner than when we left too, 10/10 will be using every time we go out of town!”
“Benjamin does such a great job with the cats. This is the second time we’ve had them watch our four cats. It’s so nice to have people who are comfortable giving medications and spend extra time hanging out with my old cats that need additional attention. Will continue to hire.”
“Erin is a wonderful pet sitter. She made sure my cat was very well cared for and loved everyday. My shy kitty really liked Erin as she would greet her at the door with lots of purrs and cuddles. I highly recommend Erin and will use her again.”
About: Big or Small, Special Needs and All—A Sniff Adventure Awaits! Hi, I'm Frankie! Animals have been the center of my world for as long as I can remember. I’ve spent my entire life raising and caring for pets of every shape and size—from cats and dogs ranging from tiny to extra-large. My home is currently run by a wonderful, chaotic crew of four: Merc: My fluffy cat who rightfully considers himself the king of the house. My Energetic Pitty: A sweet, high-energy powerhouse who keeps life exciting. My Two Special Needs Pups: One who is completely blind, and another with neurological challenges. Why Choose Me? Living with special needs pets means "cautious and attentive" isn't just a tagline for me—it's my daily reality. I have deep experience and endless patience when it comes to walking blind dogs and pups who have trouble navigating or walking in a straight line. Whether your dog is a high-energy athlete who needs a solid workout, a delicate senior who wants a slow, gentle stroll, or a special needs pup who requires extra vigilance and a patient hand, I’ve got you covered. I treat every single animal with the same customized care, safety, and love that I give my own. I can't wait to meet your furry family member and take them on their next great sniff adventure! I am currently a full-time graduate student finishing up my master's degree. Because my studies allow for a highly flexible schedule, I have plenty of open availability throughout the workweek to drop in and walk your pups while you are at the office. Treating Your Furry Family Like My Very Own In my own home, I take extreme care of my pets. Living with special needs animals and a high-energy pit bull means safety, structure, and deep attentiveness are built into my daily routine. I bring that exact same level of high-standard, vigilant care to your home and your pets.
About: I always send pictures to update the owners, and let them know what we did that day or how the animal was that way they know everything is going smoothly. Just got home for the summer from college. I’m working part time tuesday-thursday 4pm-10pm but other than that i’m super flexible. I care for people’s pets as if they were my own, growing up with animals has made me love each and every animal I see out in public, I’m one of those people who will ALWAYS ask to pet your dog.
About: I have hands-on experience caring for a puppy, including feeding, walks, supervision, and maintaining a consistent routine. I also helped teach basic commands and tricks such as sit, stay, and high five using positive reinforcement. I’m patient, attentive, and focused on creating a safe and comfortable environment for pets. I balance school and a part-time job, but I have consistent morning availability and would love to spend that time caring for your doggie! Morning walks, feeding time, cuddles, and playtime with pups are honestly the best way to start the day. I’m reliable, organized, and always make sure each pup gets the attention they deserve. Your pup’s safety and comfort are my top priorities! I carefully follow all dog parent instructions down to the smallest detail from feeding schedules to walk routes to any special needs. I respect your home, keep a clean environment, and always make sure your doggie feels safe, supervised, and loved.
“MaryAnn was great at communicating and letting us know how our pups were doing. Provided multiple photos during every visit. Was punctual for the meet and greet and every scheduled drop in. She was very sweet and left our dogs a nice goody bag of treats and toys!”
“We’ve hired Tyler to watch our cat while on vacation a few times. He exercises great communication and we know Benny always has a great time playing with Tyler. We will continue using him in the future.”
“Thanks for taking such good care of the critters and for being available for an extra day when our flight was delayed! We'll be sure to call you again for our next trip!”
About: I have had a dog all my life both big and small. I also cat sit and I’m willing to take care of all animals. Helping with your pets helps me be happy:) I am a PA student and I have classes from 10-3 most days. I am available to check in before or after class at anytime. I also am available weekends as well. I currently don’t have any pets in my home. I live in an apartment and I’m willing to go sit at your place or check in on the animals when needed.
“Very attentive to our dogs routines, and looked for ways to go above and beyond, like washing their dog bowls without even being asked. Our dogs loved him. 10/10 would hire him again.”
About: I have had dogs my entire life. From every size and breed, from Beagle to Pitbull-Mastiff mix. Imagine your anxious dog when you get home from work, super ready for a long walk... well that's me. I am a pediatric psych nurse at CHKD so I get home from work and can't sit and relax on the couch. So dog walking or sitting would help to tucker me and your dog out! If you have a strict schedule for when your pup should be fed or walked, or how much food, etc, I will do exactly what you ask. If you have a certain route or play routine, I will oblige. All in all, I want to make you and your dog happy and become a trusted and loyal person in both of your lives! I also have 3 cats so I would also be able to help with your kitties as well!
The median cost per visit for dog sitting in Chesapeake is $20
Dog parents share their Rover experiences - Chesapeake
This was our first time using Rover and I selected Jordan because I saw how many great reviews she had. When Jordan came over to meet our pitbull named Hazel, Hazel fell instantly in love with Jordan. She couldn’t stop giving her kisses. Jordan kept us informed the entire time with messages and pics of every visit. Our pup even had a few accidents and Jordan cleaned them up and adjusted her schedule a bit to accommodate our pups needs. She also walked her twice a day to help get her energy out. I would recommend Jordan to anyone needing a loving dog sitter for their animal companion!
Jelise has been absolutely amazing with Diesel during a very stressful family emergency for us. She went above and beyond to make sure he was comfortable, cared for, and stayed on his normal routine. I really appreciated the detailed updates, photos, and how attentive she was to his meals, water, potty breaks, and overall behavior. It gave me so much peace of mind knowing he was in such good hands while I had to focus on family. You can tell she genuinely cares for the animals she watches. Diesel clearly felt comfortable with her, and that means everything to me. I’m beyond grateful for her kindness, professionalism, and the love she showed my boy. I would absolutely trust her with him again and highly recommend her to anyone looking for a dependable sitter.
My wife and I had to leave my Pittie for five days. We saw Alyssa’s reviews and immediately contacted her for an in-house meeting. I was very impressed with the meeting and asked if she could watch Nina for us. During the five days she watched Nina, she was terrific!! Every time she came to our home, she sent us pictures of Nina and explained how the day went with her. She even bought Nina a couple of toys. As much as we missed Nina, we knew she was being well taken care of. It’s hard to leave our pets, but having someone like Alyssa makes it much easier. She was the best!!
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 dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for dog sitting - Chesapeake
Select a filter and find qualifying sitters offering dog sitting.Sitters in Chesapeake average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Chesapeake
Frequently asked questions about Rover
The average cost for Dog Sitting in Chesapeake on Rover is $16.65 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 Dog 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 Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 2,282 sitters on Rover offering Dog Sitting across Chesapeake. 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 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.
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 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!
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.
A Meet & Greet is a short introductory meeting between you, your dog, 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.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Chesapeake with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Chesapeake. On Rover:
- 97% of sitters can help with special care needs
- 99% can help with giving oral medications or injections
- 98% 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.
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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