Dog Sitting Chesapeake
Book a Chesapeake dog sitter to watch your dog in your sitter’s home or yours.
Over 512 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.
About: 👋Hi everybody! My name is Madison and I can’t wait to meet your fur babies! I am a current Masters student at EVMS studying surgical assisting. I am unable to work full time due to the rigor of the program so I love watching pets as a part time job. 🏡 I currently live in an apartment in downtown Norfolk with my boyfriend of 8 years, Grant. Grant helps out with potty breaks and walks if I am ever not home. We are both students and have internships so if your pet needs someone with them at all times, we unfortunately can only provide this on the weekends. 🐶I have experience with senior & adult dogs, cats, administering medications & puppies! I also volunteer at the Norfolk Animal Care Center in my free time to help out the shelter animals and be involved in my local community. We have no pets in our apartment currently. 🐱If chosen to care for your pets I will treat them with the love and respect that I would give my own pet. I love to send photo updates to the owner so that you can be assured that your pet is in safe hands. I look forward to meeting you and your fur baby! My class schedule is very flexible so I am able to offer frequent potty breaks and walks as needed! This allows me to follow the routine that your pet is already accustomed to I grew up with dogs in my parents home my whole life. My own dogs are spoiled and loved so much, so I will be sure to treat your animals the same way. My dogs love walks, playing outside, snuggles, and treats. I can promise that your animals will be treated no different than my own. I currently do not have any pets in my apartment
About: I’ve had dogs my whole life and love all animals. My dog is four and he loves playing with other dogs. I am smart and responsible and will treat your pet like my own I work part time and from home mostly, so I have lots of time to spend walking and playing with my dog and any other pets I live in an apartment, across the street from a park, so there are plenty of opportunities for walks and lots of room to play
About: Most people I know have dogs so learning how to care for them has been good so far. I know how to comfort dogs well. I work part time so there is some flexibility to caring for pets and if I’m available I’ll gladly put watching pets into my day I will be with the pet all throughout my time with them. This way they are comfortable with my presence and it’ll make them feel safe
“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!”
“Ellen was great with my 2 canine boys! Especially with my nervous one. She has a nice quiet way with animals that he responded well to. I would highly recommend her for your pet sitting needs.”
About: Hi, I’m Bridgette a passionate and dependable pet care provider with 40+ years of experience caring for dogs and cats of all ages, sizes, and temperaments. Whether your pup needs a high-energy midday walk, slow senior strolls, or company while you're away on a log workday, I treat every pet like they are my own. I’m very experienced with special needs pets that require medications or just a caring, loving hand to assist them to have the best fun time. I’m currently stepping away from the corporate world to to live in the light in the sunshine while caring for my six dogs at home so I have time to care for yours I currently have six dogs with a large fenced in yard with free range for the dogs to come and go through the back doggie door at any time with any crazy thing they find outside. I will care for your lovey with al the love I care for mine, laughter, smiles and safely. Building friendship and trust while we explore the sunshine together
About: I’ve cared for pets my entire life including seniors with medical needs. I currently have an 18-year-old cat who requires daily medication, so I’m very comfortable with administering meds and handling special routines. While I have not walked or sat much for others professionally yet, I bring decades of hands-on experience with my own pets—treating each one like family. What sets me apart is my calm, patient approach and attention to detail. I work from home, which allows me to provide consistent care, lots of attention, and flexibility with scheduling. I understand how important it is to keep dogs feeling safe, loved, and well cared for while their people are away. I work from home, which gives me a flexible schedule and allows me to provide attentive, timely care throughout the day. Whether your pet needs a midday walk, regular check-ins, or extended company, I can usually accommodate last-minute or custom requests. I’m happy to discuss a schedule that works best for you and your pet’s routine! I care for pets with the same attention and respect I give my own. At home, I maintain a calm, clean, and pet-friendly environment where animals can feel safe and relaxed. I follow feeding routines, keep fresh water available, and provide enrichment through play, affection, and companionship. My goal is always to help pets feel secure and loved while you're away.
About: I grew up around animals, both cats and dogs, and have always loved meeting other people’s dogs and cats!! I have walked dogs, most recently in DC over this past summer. I have also stayed with people’s cats. I understand how meaningful pets are to their families, and I want to be known as a safe, reliable person you can count on when you are going out of town and sadly can’t bring your pet! I will look after your pets like they are my own, even for a short period of time. I currently work full-time at a nonprofit in Virginia Beach. My apartment doesn’t allow for pets, so I thought Rover would be a great way to be around animals in the time that I cannot have my own. I am very active, so I love going on walks with dogs, and I am happy to spend my weekends hanging out with your pets. While I am often not available from 9-5 on the weekdays, I am available for weekends and after 5 on the weekdays, in case you work different hours than I do and need someone to check in on your pup or cat! I completely understand the love and value we have for our homes and our pets. While I cannot have pets in my apartment, I can guarantee to respect your home and treat it with the utmost care, while making sure your pet is safe and having a good time!
About: Hi there! I'm a retired U.S. military veteran with over 20 years of service, now dedicating my time and passion to caring for dogs in the Norfolk, VA. I am the proud owner of a trained Belgian Malinois and a sweet Yorkie, so your dog will be welcomed into a home that will have an understanding on how to care of your pet. Since, I have had my Malinois she has taught me more skills that I could ever imagine. I have also been to a dog training school in order to provide a better understanding on how to communicate with my girls and with other dogs. I am not a dog training, but I have been using my new skills to teach Pynky (Belgium Malinois) to have a much more well-balanced dog. I am a retired Navy veteran for 10 years and spend alot of time with my household needs and of course spending time with my Pynky and Maya they both keep my husband and I busy. Despite my daily activities, my dogs are well taken care of, we go for daily runs and other needed activities from ball playing, retrieval and agility exercises needed to keep my girls well-balance and healthy. Your fur babies will be treating just as instructed by their parents whether high to low drive, I will meet their needs. In my daycare and boarding I will meet their needs with daily walks, playtime, feeding, medications etc... We do have a fence backyard, also have a dog park about two blocks away from my house. We also have a big space behind my back yard that we utilize on a daily basis especially for my Malinois. Inside my house they have a good space to walk around and relax.
“Anna was amazing she was took care of my animals as if they were her own. She was very respectful of my home, she always kept up with communication on my fur babies. I would definitely use her again.”
“Ashlynn is wonderful! She was flexible with my changing schedule and kept in contact with me throughout my trip. She sent lots of pictures and my dog looked very happy spending time with her. I will definitely book Ashlynn for my next trip!”
“We love having Damian sit our cat! He’s detailed in his visit notes, kind, and friendly. He makes us feel assured she’s in good hands. She likes when he comes to visit and she’s always in good health and happy when we come back. Definitely recommend Damian’s services!”
“Judy was absolutely amazing! She made the entire experience stress free. She was reliable, communicative, and sent me updates and photos, which gave me so much peace of mind while I was away. She took great care of my cat, respected her personalities and boundaries, and genuinely cared about her wellbeing.”
The median cost per visit for dog sitting in Chesapeake is $20
Dog parents share their Rover experiences - Chesapeake
Alyssa has been such an absolute blessing, she has done so much to take care of and provide for both of my pups. She has helped me so much and I really can’t thank her enough for all that she has done for us. She’s been teaching June tricks and helping them learn how to be potty trained. While I am at work I have peace in mind knowing that my fur babies are in great hands. I also appreciate Alyssa for being very understanding when the schedule changes. She bought both of my pups a little toy and she always takes many amazing pictures for me to look at while I’m at work. My husband and I are both so happy we hired her to look after Lady and June. Thank you so much Alyssa!
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.
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 to book dog sitting
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 7 repeat dog sitting clients
FAQs for Dog Sitting - Chesapeake
Frequently asked questions about Rover
The average cost of Dog Sitting in Chesapeake is $14 per visit as of November 2026. Most bookings cost between $13 and $22 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 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.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
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:
- 89% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 95% 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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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