House Sitting in Chesapeake
Find a loving house sitter to watch over your pets and your home.
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Top rated Chesapeake house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Felicia was amazing! We came home to happy dogs and a clean home. Thank you for everything. We’ll be in touch for another upcoming trip we’ll need your services for!”
“This is the third time Jordan has worked with us. She is just as amazing every time. Martin is always given so much love and taken care of so well. We really appreciate having someone to watch him that we know he is completely safe and happy with! We will continue to work with her in the future.”
“Erin was amazing! She was very easy to communicate with to set up the booking, asked plenty of questions to make sure Diablo and I were taken care of, and sent me picture and video updates of them enjoying each other's company. If possible, I will book her again in the future!”
“Amy was so great with our dogs!! She walked them, hung out with them, and kept us updated with photos. She was always quick to respond and made us feel totally at ease while we were away. We came home to happy pups and a spotless house - such a great feeling. Highly recommend and would 100% book with her again!!”
“Loki was wonderful with our three little girls! He sent great pictures and kept us up to date with all of their antics 🤣 He was a pleasure to work with and we will most definitely be using him in the future!”
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.
“Hannah is awesome! Booked short notice and she took wonderful care of my 2 year old lab . Very communicative and sent lots of updated and photos. Highly recommend.”
“She was great! My furbaby uno really loved and enjoyed his time with her. She was very communicative and kept sending pictures and keeping me updated which I really liked. She is definitely becoming our permanent doggy sitter.”
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.
“Tracie is great with my 3 babies! She always shows up on time I always feel safe knowing she is watching over my babies. I would definitely recommend her for any pet sitting needs!”
“We had such a wonderful experience with Abi while we were away! She took amazing care of Loki and Hazel, and I truly felt completely at ease knowing they were in her hands. Hazel is a very anxious dog and rarely warms up to new people — she never goes on walks with anyone but us — and she actually went out on a walk with her! That alone speaks volumes about the patience, kindness, and calm energy she brings. Both dogs were happy, well cared for, and clearly loved while we were gone. I’m so grateful to have found someone we trust so fully. We will absolutely be hiring her again and again!”
“Emmanuel was an amazing pet sitter! He watched my 5 fur babies while I was gone for a week and they got along with him so well! He was very attentive to my fur babies and he enjoyed time spent with them! He treated them like they were his own. He was very communicative, providing me daily updates with adorable pictures and videos! He even got my antisocial cat to warm up to him and interact with him, which was a 1st! He also did a great job keeping the place clean while caring for the fur babies. I feel like my pets definitely lucked out with having an amazing sitter and new friend! I would highly recommend booking Emmanuel as your next pet sitter!”
“Tyshaun went above and beyond with helping my pup while she was dealing with IVDD. He had the patience to take care of her when she could barely walk. He also gave my other three pups the attention they needed. I highly recommend Tyshaun.”
“Emma was FANTASTIC with our two little guys (dogs), one is a Maltese and the other is a mini Golden Doodle. Usually, they do not eat at least the first day and usually not for two or three days if we leave them with someone, which has always been people our dogs know and love. Not so with Emma; she was able to get them to eat their first meal and every meal thereafter. You could tell by the pictures, etc. that they were happy and enjoying her in our home, where she stayed with them for a week . . . in our home overnight that is. When we returned, of course, our pups were very happy to see us (almost overwhelmingly so) but it was a true telltale sign when they ran to the bedroom door where Emma stayed, and they started to whimper when they realized she wasn't there. We will definitely be using Emma again in the future. I recommend her without hesitation or reservation to watch your pets/family.”
“Morgan was awesome with Ginger and the house. She was engaged with her and made sure she had lots of playtime. She was reliable, prompt, good communicator. and a great listener. She did everything I had asked for. Ginger enjoyed her company :)”
Over 1,201 pet parents in Chesapeake have booked house sitting
Chesapeake pet parents share their Rover experiences
We could not recommend Sara enough! She has an obvious love for all animals, that translates very naturally into her care for them. She offered a meet and greet before her stay and provided updates throughout the weekend. We absolutely will trust her again with our home and animals, and recommend her to other friends and family in need of a sitter.
Our dogs had a great time with Brieana and settled in with her right away! When we got home, it honestly felt like we had never even left. She took great care of them, kept us updated, and treated them with so much care. We’re really grateful to have found someone we trust with our pups, and we’ll definitely be booking with her again!
We loved having Abi care for our pups for several days. She was frequently in communication with us, sent lots of pictures, and was honest about our dogs temperament and needs (especially since we have an older dog that more recently had surgery). Our dogs clearly looked happy and well cared for when we came home. Thank you!
Cameron was phenomenal with our Bootsy boy! He was really patient during the initial meet up as Boots took a few minutes to warm up and they were besties by the end of it. Cameron asked great questions to make sure he was fully informed on Boots' routine prior to us leaving. He sent pics and videos throughout and even taught Boots a new spin trick! Our house was left very clean and he stripped the bed for us before we got home to wash things. My husband and I would highly recommend using Cameron to anyone in the area!
London did a fantastic job caring for Millie while we were out of town. She is very communicative and timely in her responses. London’s flexibility to stay an additional day due to a canceled flight made the change of plans way less stressful. We knew Millie was in good hands with her, and would absolutely rebook in the future.
Naja took great care of our 2 dogs and our home while we were on vacation. She sent frequent updates and was comfortable asking questions and informing us of the dogs' behaviour in aour absence. The biggest comment my wife and I have upon our return is that the house was clean and tidy, and the dogs were calm and happy. They had a bond with Naja that was clearly evident even in our presence upon our return. I think that is the true sign of the caring petsitter that Naja is. We would absolutely recommend her and will hope to use her services again.
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets 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!
The median cost per night for house sitting in Chesapeake is $42
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 house 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.
Sitters in Chesapeake average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chesapeake on Rover as of Jun 2026 was about $42 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 1,250 house sitters in Chesapeake. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 90% of Chesapeake house sitters respond in under an hour.
House sitters in Chesapeake have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Chesapeake.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chesapeake house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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