Dog Sitting in Chesapeake
Book a Chesapeake dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Chesapeake dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
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.
“Haley was incredible! We were nervous about leaving our puppy alone for the first time, but she came to do a meet and greet to get to know our puppy which made us feel so much better! She always gave lots of picture updates, made sure he pottied and had lots of play time during her visits as well! We plan on booking her again if we need any other drop-in visits! Thanks, Haley!!”

“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!”

“Theresa was amazing in assisting us with our last minute catsitter needs! She was able to provide her services for more than a month (almost 2!!) & accommodate any requests we may have. Would definitely rebook again if needed. Thanks so much, Theresa ❤️”

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.
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.
“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!”


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.

“Casey is a spectacular sitter and I would definitely book her again. I appreciated her cleaning up after my Archie and giving him all the loves during my trip. She made my vacation stress-free!”

About: My name is Catina Lewis. I have a very flexible schedule. I work at a physical therapy office as a patient coordinator. Navy wife, with a crazy 6 year old, a beautiful 3 year old, 6yr old Pom mix, Australian Husky Mix, Great Pyrenees and a Princess Cat. I have live in VA for 7 years and have been on Rover doing dog sitting for 6 and I love every minute of it! I currently live in a 5 bedroom home. I also have a decent backyard they can play in along with mine and possibly 2 other pets. ~Meet and Greets~ I do require we do a Meet and Greet 3 days before booking a stay. I want to make sure the animals are comfortable with each other for the safety of both mine and your pets. **Policy Pick up and Drop Offs** Times are 8am-8pm *During pick-ups and drop-offs text messages will be greatly appreciated due to us having multiple dogs and our children who nap and sleep in. *Rate covers 24hrs period. Ex: Pup’s parents booked a 2 night stay, beginning Monday and ending of Wednesday. Pup gets dropped off at 8am on Monday for 2 night boarding. Once Wednesday rolls around, Pup pick up time is 8am; if pick up time needs to be extended to later than 8am, a single Doggy Dare Care will be applied to the full amount. *That being said — we are human and things happen and plans fall through. I am flexible but please inform me as soon as possible if anything comes up. I also have plans and kids that go to be at current times. Please inform me before the stay what the anticipated drop off and pick up times are so we can plan accordingly. Someone will always be home with them to let them out or feed them. They are let out every 2-4 hours and feeding them separately from our dogs or any other dogs we have in care for safety reasons. I have a fenced in yard and 4 adorable doggies to keep your company. We are always outside playing fetch or just hanging out so they get enough exercise.
“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.”

“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!”

Chesapeake dog parents share their Rover experiences
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!!

Popular requests near you
Select a filter and find qualifying Chesapeake sitters!How Rover works

1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
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!
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Chesapeake.
Rover makes it easy to find Chesapeake dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.



















