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.
“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!!!”
“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.”
“Haley is the best! She took great care of Simone and Trixie for a month. They are going to miss having her stop by all the time. Made being gone completely stress free for me. Highly recommended Rover!”
“This was our first time booking with anyone, and it was just a drop in visit for a few hours while we were on a day trip, but it was just perfect. Kelsey let me know when he had arrived and sent me lots of pics (which I loved) and kept me updated on how it was going. We had good communication back and forth and it was a great peace of mind for me to know the dogs were all good. They had a great break with Kelsey and lots of time to be outside if they wanted, or to cuddle with Kelsey as one of them did a great deal, and just overall a nice social break in their day.”
About: Hi! Before Rover, I lived in Japan and personally took care of dogs of all sizes and 3 cats. It was the best time I had and I don't mind doing it while I'm back in the US! I typically get off around 3pm! Off during weekends unless I pick up a shift I'd let you know. My daily walk usually last a couple miles and I wouldn't having furry friends tag along! I have an apartment that allows pets, I also am willing to house sit! My apartment is spacious and I go on long walks myself, so why not have a tiny companion!
“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!!!”
“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.”
“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 have been around dogs since I was about 8 years old and have experience with both small and large breeds. I have owned 4 dogs myself and caring for dogs has always been something I genuinely enjoy. Over the years, I have gained experience with dogs of different ages, sizes, breeds, energy levels, and personalities. I understand that every dog has unique needs and routines, whether that means lots of playtime and exercise or a calmer, more relaxed environment. I am comfortable with feeding schedules, walks, basic care routines, and giving dogs the attention and patience they deserve while their owners are away. As a pet owner myself, I know how important it is to trust the person caring for your pets. I will always treat your dogs like my own and provide reliable, loving, and attentive care. I’m currently working a flexible schedule and I am most consistently available in the afternoon and evening times during the weekdays and fully on the weekends to provide extra time for your animals! I have a fully fenced yard and the space/ability to crate as needed. I do currently have 2 friendly cats in home who are used to other cats/dogs. Each member of my household has experience with cats and dogs and would be excited to show yours some love and attention up close or far away! I always prioritize creating a safe, calm, and comfortable environment for every pet in my care. I understand that every animal has different needs and personalities, so I take the time to learn their routines, preferences, and comfort levels whether inside your home or mine.
“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.”
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.
“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.”
About: I'm a go to friend when it comes to taking care of pets, and I own two cats myself. I'll feed them, make sure they go potty or their box is scooped, they'll get play time and lots of pets! I work full time monday-friday, so I have open weekends. Have an unexpected weekend trip? Places to be? I'm the sitter for you! I'll make sure to gently introduce myself to your pet and take the time for them to trust me. I will make sure to take the time to sit and play with them and give them extra attention. I like to keep things clean and tidy so I will pick up any accidents or messes on top of keeping their food and water clean and their litter box clean.
“Emily was great with my cat Tumbleweed! She sent lots of pictures with written descriptions of what went on and how he was doing and I came home to a happy and healthy cat!”
“We’ve hired Tyler to watch our cat while on vacation a few times. He exercises great communication and we know Benny always has a great time playing with Tyler. We will continue using him in the future.”
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.
“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. 🧡”
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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