Dog Sitting Chesapeake
Book a Chesapeake dog sitter to watch your dog in your sitter’s home or yours.
Over 1,408 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: Due to frequently moving around for my moms job, I wasn't able to have a pup to myself, however that never stopped my from caring for others. Where ever we called home, I became the go-to pet sitter in my community. In the beginning I advertised myself to my moms coworkers and before I knew it, people already new my name and would refer me to others. I was only allowed to care for these fur babies on school breaks during my primary years and I still do so now when I visit my mom overseas. In the past I have done boarding, drop-ins as well as walks. Walks: I usually walk dogs about 3-4 times a day. At wake up usually around 8am around human lunch time (noon) another about 4 or 5pm and another before bed 10/11. My walks usually span from 15-45 minutes. Lunch walks are on the shorter side as well during peak heat hours. Longer walks are morning and afternoon/night times as I have more time to dedicate and its usually cooler. If your doggie needs more or less walks/time outside I am happy to accommodate. Attention: I am more than happy to accommodate to your pups personality and regular home life. If your doggo loves cuddles and kisses I am free for all the above but if that is not their style let me know and can provide space for alone time (or parallel laying lol). I allow pets on my bed but if this will interfere with their learning and home training, let me know these limitations. Playtime: I usually play with pups when they show signs that they will like to play. Whether they have the zoomies and we round around or if we are playing tug-a-war. If you have a more active dog, I will accommodate with more activities and longer walks. If they enjoy running I can also comply as I am trying to get better at running. If your dog has a preference for dog parks, let me know so I can accommodate as well. Being a college student, I am flexible when it comes to a pups needs. I work a part-time job as well as attend classes but, I live a block away from both so quickly getting home or to my car is not a problem. I am a pretty active person as I like to walk and experience nature to its fullest. I know some nice spots to walk and stretch your doggos legs. I also know how to get comfortable and cuddle :) For this fall semester I have classes during the day and have a part-time job during the evening (3-4h) but I am able to work a proper, caring schedule to care for you babies. I have two roommates that also are a fan of dogs so attention for your fur baby isn't a worry. I also do have my own room with plenty of space incase a dog is uneasy with people or shy. I live in a safe neighborhood with space to also have walks. Feedings: Please provide their bowls, feeding schedule, allergies, how you prepare your the food, etc. Environment: I am about to be in between leases however, I have a place to stay and a place to accommodate for your pups. Once I move into my new place I will upload photos. Emergencies: PLEASE provide me your dogs medical records as well as your vets number and location. This is for emergencies only and I will contact you first if anything arises.
“My shy cat took to Michelle right away. I felt better leaving to go out of town knowing she was caring for Coco. She let me know how Coco was doing and posted pictures each day.”
“Amy was wonderful with our older puppies while we were on vacation. She took extra care of any accidents and made sure they always had exercise and love. We always received updates every visit and you could tell our pups were so happy. Extremely happy and appreciative for her care for our fur babies.”
“Alexis is super, super sweet and did such a good job taking care of our kitty while we were away! She was available for a super last minute booking and really went above and beyond with the time she spent and her ability to deal with the unforeseen challenges with our kitty’s feeder dying while we were away. She did an amazing job and we would absolutely book her again for future travel.”
About: I walk dogs for my local animal shelters frequently and i have raised and trained all of my dogs (i had 4) form when they where puppies so adults. I am a college student in my senior year, so my schedule is fairly flexible. However, my best availability is on the weekends and fridays. I have so much respect and love for animals, and I understand that they are family and someone’s babies. I’m happy to follow your pet’s routine and do whatever they need to feel safe, comfortable, and well cared for.
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.
“I can't recommend Morgan enough! She took amazing care of my 2 dogs while I was away and followed every instruction perfectly. She made sure they got plenty of attention and even played fetch with my golden during every visit, which she absolutely loved. After it rained and the dogs tracked mud through the house, she even went above and beyond by mopping my floors without being asked. It's clear she truly cares about the pets she watches, and takes pride in doing a good job. I felt completely at ease 200 miles away knowing they were in such great hands, and I'll absolutely be booking with her again!”
“Tyler did a great job with drop-in visits for my cat, Gina. He kept me updated with messages and pictures, so I always knew how she was doing while I was away. I really appreciated his communication and care—definitely grateful and would recommend him!”
“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!”
“Geneive was fantastic! She kept me posted on when she arrived, and sent photos of my dog during the stay. She put my mind at ease and I knew my dog was in great hands.”
“Aimee was attentive and so sweet with my cats. Even though it was just one visit, she really made my cats feel loved. Absolutely am gonna keep Aimee around. Such a sweet person and gentle soul. Obviously loves animals and her experience is evident in her handling of even my most dramatic cat. They look forward to seeing her again! Thank you, Aimee!!!!”
“Eleanorah is amazing! She goes above and beyond and always leaves detailed descriptions of everything that was done plus always sends lots of photos! She was also able and willing to accommodate last minute schedule changes due to me being deployed. Incredibly sweet girl, highly recommend!”
About: I’ve always lived in a house with at least one dog. I also have experience dog sitting my aunts 3 dogs over the summer. I grew up around a rabbit, a bird, dogs and cats and I loved every part of it! I’m available Monday, Tuesday, Thursday, and Friday from 4:00 PM–10:00 PM. I also have flexible availability on weekends for walks, drop-ins, and other pet care needs. I’m happy to coordinate times with pet parents based on their pet’s routine. I have a fenced in back yard with a lot of space! I also have a very friendly and hyper jack russel terrier who is 2 years old! He loves to play with other dogs. I usually have play time outside with many toys and balls. I do walks at least twice a day. I keep my eyes on them inside and outside the house to make sure they are okay.
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.
The median cost per visit for dog sitting in Chesapeake is $20
Dog parents share their Rover experiences - Chesapeake
Nick was awesome. He was very accomodattentive to our senior pups schedule, especially our furbaby who is a diabetic and required 2 shots a day. He provided daily updates and let us know if someone had an accident in the house. We really appreciate him and would recommend him to our family and friends. THANKS NICK
Felisha was over the top when it came to taking care Joey. He took to her very quickly and looked like he had a great time while we were away. Even when he got a 24 hr bug she was able to get him feeling better in no time. We will definitely call on her again when we go away
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
It's that easy! All payments are processed through Rover's secured platform
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 Dog Sitting - Chesapeake
Frequently asked questions about Rover
The average cost for Dog Sitting in Chesapeake on Rover is $16.65 per visit (as of September 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 September 2026, there are 2,287 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
- 100% 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.
Connect anywhere with the Rover app
