Dog Sitting Chesapeake
Book a Chesapeake dog sitter to watch your dog in your sitter’s home or yours.
Over 1,380 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.
“Ellen stayed overnight in our home and did a great job of taking care of Skyler and Lily. I’m very detailed oriented and left instructions all over the place and Ellen followed them to a tee. She sent lots of pictures while we were gone and didn’t hesitate to contact us if she had a question. I highly recommend Ellen!”
“Casey was very thorough and thoughtful caring for my three dogs. I have one dog who is a senior and another who has heart issues. Casey confirmed their medications were administered at each visit. She let me know they were eating and drinking, and included any points that might be of concern. She included lots of pictures too. She also planned her time each visit to make sure they had some time to wind down and have a drink inside after play time outside. Her clear notes showed how attentive she was to them and gave me a lot of peace mind.”
“De was a wonderful dog sitter! I did the 60 min drop in visit, and I feel that De went above and beyond for my dogs. My dogs are pretty particular about certain things and she was very good at making sure my dogs were comfortable.”
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.
“Rachel has been the best dog sitter that I’ve had! She has been checking in on my fur baby for a while now while I’ve been at work and is always on time and very communicative. Would 100% recommend!”
“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.”
“Renee is so amazing with our wild wolf pack! We always look forward to her coming to hang out with our dogs when we head out of town or need to leave the house for an all day long event. She keeps us informed of how our dogs are doing, sends photos, and follows up with a message. We are so lucky to have found her and she is always our first choice when it comes to someone taking care is our dogs.”
About: Reliable & Loving Dog Care You Can Count On Hey there! I’ve been caring for dogs for as long as I can remember, whether it’s for family, friends, or anyone who needs a trustworthy sitter. Being reliable and consistent is why I’m the one people call time and time again to watch their fur babies. From neighborhood walks to fun rides to the dog park and even playdates, I make sure every dog in my care gets the attention, exercise, and affection they deserve. Your pup’s safety, comfort, and happiness are always my top priorities. I currently work Monday–Friday from 9:30 AM to 6:30 PM, but outside of that I’m fully dedicated to giving your dog the best care possible. Whether you’re looking for drop-ins, walks, or weekend care, I’m here to help make life easier for both you and your furry friend. I can’t wait to meet your fur baby🐾❤️ I am currently a college student working overnights at the hospital, my schedule is pretty flexible when it comes to work. Majority of the time I can fur baby sit on weekends and during a busy week! My current working hours are from 19:00-07:00 three days a week. I love to accommodate anyone I work for, as the current couple I fur baby sit for I watch their fur babies in their home. As I ensure all animals are taken care of, fed, cleaned, & their household is left the way they like it when they return home. Taking strolls around the neighborhood for the doggies and leaving blinds open so that the cat can sun bathe leaves both fur babies happy.
“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.”
“Abby is incredible! I had to cancel last minute with another sitter due to bad vibes and she responded so quickly and with any/all information I could want or need! This was the first time leaving Riggins alone at home while on a quick vacation and during her check-ins with my cat she sent as many pictures as possible and kept me well informed! It put me at ease. She is just the sweetest! I will be using her services from now on!!”
“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!”
“My dog has gained a new friend. Geneive was kind and loving towards Nola. Giving her treats, feeding, and daily walks, really keeps Nola happy and in her routine. From all the pics and chats, Nola seemed to feel like her sitter was a part of the family. I would definitely book with her again and recommend her to others. 🧡”
“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: I have many years of experience caring for family pets as well as raising beagle puppies from birth to adoption. I have experience working with dogs, cats and small birds. I am very attuned to animal body language and can read behavioral cues very well. I help care for my family dog by letting her outside for potty breaks throughout the day as well as feeding 2 times a day. I also spend quality time with her in the form of playing and walks My first priority in my day is to make sure the pets' needs are met so that they may be comfortable while I continue my daily tasks throughout the day. Feeding times are at regular intervals.
“Benjamin showed up to all appointments and managed our high needs cats food and medication routines wonderfully. Benjamin also went above and beyond to bring in our packages and bring our trash cans up while we were out of town.”
About: Dogs are my absolute favorite! I couldn't think of a better way to spend my days than loving on your pup! Dog walking, check ins, or overnights. I am available for anything to help. I am a travel CT tech. My schedule varies so just reach out to me and we can try to find something that works for both of us! I live in a complex so there are no busy roads and no fast driving. There is plenty of space for walks and playing in the yard. I am also willing and able to take your pet to a dog park if that is something you would like.
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
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 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 August 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 August 2026, there are 2,279 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.
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