Dog Sitting Chesapeake
Book a Chesapeake dog sitter to watch your dog in your sitter’s home or yours.
Over 1,331 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.
“Jackie is fantastic! She went above and beyond for our pets while we were away. She took time to love on each of them and sent lots of pictures and updates throughout our trip. The peace of mind knowing they were in good hands was exactly what I was looking for.”
“Joanna is fantastic! We are only in the second week and my little Zoe is thriving! She loves to go on walks with her!! Love her updates from their visit!! Thank you Joanna!!!”
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.
“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!”
“Hannah was an amazing sitter! She took great pictures of my cat as well as pictures to make sure I knew he had food, clean litter and water! I would definitely recommend her and will be using her again in the future!”
“Kylie was awesome with our pets! She made time to come by beforehand to meet all of them and make sure she knew where everything was. We got pictures and updates with each visit to let us know what was going on and she communicated any issues or concerns. You can tell she really cares about the animals she’s watching and pays attention to their needs.”
About: Hi! Im Erin and I LOVE animals! They are our "furry babies" and we have a duty to make sure they are well taken care of like any other family member! I've been caring for pets since I was a child and have welcomed several breeds and varieties in my home over the years from cats, dogs, birds, bunnies, snakes, turtles, even horses and pigs! I have a cat and a bunny who are friendly and love meeting new pets! My cat Oliver is a loving and cool "big bro" and my bunny Lucy will keep everyone happy and energetic! I know its hard to leave those precious babies home alone while you work all day so let me be their "best friend" when you need the help! I am an Insurance Agent so I work from home most of the week. I have my weekends off but I have time during the week to care for your pets in between meetings and in the evenings. I am not hosting at the moment due to renovations in my home, but I will gladly come to your home to take out your pets or to feed and keep them company while you are away on business or holiday. I am willing to stay at your residence to care for your pets if accommodations are available. I will be willing to wash and perform light grooming if needed and take them where you'd like with and other amenities your pet may need. All can be discussed and negotiated for the situation.
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.
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.
“We are so grateful to have had Haley as a sitter for our puppy Jax. She is so attentive, always on time, and just a bundle of joy. Jax loves when she comes around and always has a good time. Thank you so much!”
“Emily did an excellent job taking care of my 16 yr old cat while we were away. She was responsive, reliable, and made sure he got his medicine twice a day during her drop in visits. I would highly recommend her.”
“Abi was a great sitter for my pitbull over a long weekend. She provided updates and took great care of her. I can tell she cares a lot about animals. We'd absolutely use Abi for drop in visits again. Thank you Abi!”
“Tayauna provided extraordinary services when caring for my cat, Lily Rose, while I was away on a trip. As many of us understand, it is not easy to be away from our beloved pets. Taya helped give me peace of mind through the daily updates and photos. She went above and beyond to provide the best care for Lily, and she blessed my heart as well. When returning, Lily was so happy and I believe the quality of attention and care that was given to her made all the difference. Thank you so much Taya! Lily is looking forward to spending time with again in the future, and I am beyond grateful to have a cat sitter who I can trust to do an excellent job. God bless you!”
“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 love interacting with animals and especially dogs. I have looked after friends cats and dogs before. For walks I am good with dogs that move at all paces: fast or leisurely. My family's dog is a 14 y.o. mini dachshund and I have loved watching & caring for her at all stages of life. I am looking to walk/care for dogs on the weekends as this is my most available time. I work longer days as a physical therapist throughout the week. I care for my pet personally & others by showing lots of love by giving belly rubs, treats, playing with pets or letting them lounge. I ensure the environment is safe by keeping an eye on pets in the home or in the yard, whether they are playing or taking a potty break.
“Amy was great with dropping in on our two dogs while we were out of town! She was super communicative and sent great updates and pictures. I know our pups were as well taken care of as they could be!”
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.
“Chelsea was such a great care taker of my 2 outdoor cats. She met with us before our booking. She even took care of a package while were away. Pictures were sent every day. Thank you Chelsea.”
The median cost per visit for dog sitting in Chesapeake is $20
Dog parents share their Rover experiences - Chesapeake
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. 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 sitters!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 June 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 June 2026, there are 2,283 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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