Pet Sitting in Chesapeake

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Chesapeake pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Ayla P.
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Ayla P.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
5 years of experience
Norfolk, VA, 23507

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.

Sitter Profile Image: Jeanne H.
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Jeanne H.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
40 years of experience
Greenbrier East, Chesapeake - Greenbrier, VA, 23320

This is our first time using Rover. We wanted someone who was mature and responsible and Jeanne was a great fit. She was prompt and caring from the start. She sent messages and pictures every time and followed the details of our instructions. She was also thoughtful and thorough in how she cared for our kitty. We especially appreciate Jeanne giving time and space for our kitty to warm up to her and make sure she was comfortable with interaction. We recommend Jeane!

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Dj A.
Sitter Profile Image: Jordan H.
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Jordan H.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
197 reviews
55 repeat clients
31 years of experience
Portsmouth, VA, 23704

Came home to my two boys perfectly happy, well cared for, and fed. Thank you Jordan for looking after my babies! And for the pics too. ⭐️⭐️⭐️⭐️⭐️

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Liz P.
Sitter Profile Image: Teresa S.
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Teresa S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
173 reviews
72 repeat clients
12 years of experience
Portsmouth, VA, 23704

Teresa was an absolutely amazing cat sitter! She was so genuine and playful with them. I loved all the updates I got - pictures & little messages. I knew my cats were in great hands. Teresa is very patient and trustworthy! I would definitely recommend!!

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Carina S.
Sitter Profile Image: Hannah P.
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Hannah P.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
20 reviews
9 repeat clients
3 years of experience
Indian River, Chesapeake, VA, 23325

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!

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Haley P.
Sitter Profile Image: Morgan K.
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Morgan K.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
10 years of experience
Indian River, Chesapeake, VA, 23320

About: i’ve taken care of animals since I was a kid and have had lots of dogs that I absolutely adore. I love just being around animals and will always do my best to make them feel safe and comfortable I am currently a college student and I want a job where I have more flexibility. I have a lot of free time and to me would rather spend it with animals over other things. I am very good with lots of different dogs and am very attentive so in your home I will make sure to be respectful of their space and treat them with the upmost care.

Sitter Profile Image: Beth C.
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Beth C.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
93 reviews
27 repeat clients
20 years of experience
Indian River, Chesapeake, VA, 23325

Beth helped me out when my sitter fell through and I was already out of town. She was able to jump in with barely any notice AND I cannot express how thankful I was for her flexibility to help me out on a holiday. My two dogs looked so happy in all of the picture updates she sent. I would definitely book again :)

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Ally M.
Sitter Profile Image: Felicia H.
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Felicia H.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
17 reviews
4 repeat clients
5 years of experience
South Norfolk, Chesapeake, VA, 23324

Felecia was so awesome! Resun and Roxy absolutely love her I can tell and are very comfortable with her. They even let her bathe them lol. We appreciate her patience during the 2 meet and greets as well for she did not have to do that. She took great care of our home EVEN washed their dog bowls out🫂☺️ We are grateful to know her and be able to travel freely now without worry. Thank you Felecia! See you again soon

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LaStashia L.
Sitter Profile Image: Theresa L.
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Theresa L.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
310 reviews
110 repeat clients
35 years of experience
Norfolk, VA, 23509

Theresa never fails to help us, especially in times of need. She is so patient and kind to our girls and it makes being away from them all day an easier task. We can’t thank you enough!!

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Nicole R.
Sitter Profile Image: Tiffany M.
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Tiffany M.
from
$13
per visit
5.0 out of 5 stars
664 reviews
148 repeat clients
15 years of experience
Virginia Beach, VA, 23462

I’ll let the real customers leave the review: Katie: “We love it when Tiffany comes by to let us outside.” Bella: “And she lets me give her wet beagle kisses!” Sherlock: “And she gives me a treat. She’s the best!” Having Tiffany let the dogs out while we are at work has been very helpful. My dogs highly recommend her!

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Daniel T.
Sitter Profile Image: Eleanorah-Pearl A.
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Eleanorah-Pearl A.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
31 reviews
9 repeat clients
7 years of experience
Norfolk, VA, 23513

About: I adore caring for animals as if they are my friends because they are! Im experienced with dogs and many animals alike from working at dog daycares and on farms, I also am very skilled at drawing and writing report cards!! I care for animals daily with an open and available schedule! Im ready to have more regulars and build trust and a bond with your fur babies for the best care and experience. I provide entertainment and love! I currently care for my cat Spider and a pit named Loki! I adore them. I let Loki play in the back yard with many other dogs so they keep busy! He is so friendly and always down for a play date. I’m currently reading about dogs and certain training exercises because I enjoy animal behavior and care deeply about their safety and mental wellbeing.

Sitter Profile Image: Grace B.
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Grace B.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
49 reviews
25 repeat clients
25 years of experience
Portsmouth, VA, 23707

Grace was amazing! Our previous sitter dropped out last minute, Grace was available and responsive and we were able to get everything sorted 2 days before we left. She even got our shyest cat out and about and made sure to send plenty of action shots of the cats playing!

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Katelyn L.
Sitter Profile Image: Kylie P.
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Kylie P.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
24 reviews
7 repeat clients
10 years of experience
Norfolk, VA, 23510

Kylie was awesome with our pets! She made time to come by beforehand to meet all of them and make sure she knew where everything was. We got pictures and updates with each visit to let us know what was going on and she communicated any issues or concerns. You can tell she really cares about the animals she’s watching and pays attention to their needs.

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Ivana C.
Sitter Profile Image: Maggie O.
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Maggie O.
from
$17
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
9 years of experience
Norfolk, VA, 23507

Maggie did a fantastic job looking after our older cat over the holidays. She was very communicative and sent us the cutest pictures every day. We came home to him happy and healthy, which is everything you want from a sitter! Thank you!!

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Austin E.
Sitter Profile Image: Tyler F.
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Tyler F.
from
$20
per visit
5.0 out of 5 stars
81 reviews
29 repeat clients
20 years of experience
Norfolk, VA, 23507

Tyler was very patient with us using Rover for the first time and took great care of our cats! He played with them and sent pictures on a daily basis. Even my cats could tell that he has a great spirit and weren't scared of him a bit, which means a lot!

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Alina S.
Sitter Profile Image: Stephanie G.
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Stephanie G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
61 reviews
23 repeat clients
27 years of experience
Greenbrier West, CHESAPEAKE, VA, 23320

We have used Stephanie on several occasions to drop in on our doggie babies and she is a God sent. Our pups love her and she is extremely loving and patient with them. During our last trip, one of our babies got sick and she sprung right into action, even cleaning up the mess. Having her to look after our pups truly gives me a peace of mind and I would recommend her to anyone.

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Nekeysha L.
Sitter Profile Image: Zara M.
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Zara M.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
73 reviews
23 repeat clients
10 years of experience
Portsmouth, VA, 23707

Zara definitely has a way with animals. My dog doesn’t like everyone and he warmed right up to her. I would highly recommend her and I hope she’ll be able to watch Petey many more times in the future.

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Shannon D.
Sitter Profile Image: Hannah W.
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Hannah W.
from
$20
per visit
4.9 out of 5 stars
42 reviews
7 repeat clients
40 years of experience
Indian River, Chesapeake, VA, 23325

I’m the type of person who said I’d never be able to let a stranger watch my babies. I found myself in a position where I needed to break that rule and Hannah was so wonderful that I wasn’t stressed at all about leaving her with my pets. She and her daughter came over every day to play with, feed, and care for my babies. She was very communicative, innovative when any pets might not eat enough or seem too stressed, and knowledgeable. She was willing to try any ideas I had on how to help my pets cope, too (my dog especially is a very anxious boy). I truly believe that Hannah and her daughter loved my pets like I do and I couldn’t be happier with how their visits went. I cannot recommend Hannah enough.

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Julia S.
Sitter Profile Image: Heather R.
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Heather R.
from
$18
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
5 years of experience
South Norfolk, Chesapeake, VA, 23324

About: Hi! I'm a lifelong animal lover with years of hands-on experience working in animal shelters, dog daycare centers, and boarding facilities. Caring for animals has always been a huge part of my life, and I truly enjoy getting to know each pet's unique personality and needs. After recently losing my beloved dogs, I realized I wasn't quite ready for another long-term commitment, but I deeply missed having dogs around. Rover has given me the perfect opportunity to open my home and heart to dogs while helping other pet parents feel confident their pets are in good hands. I'm a stay-at-home mom, which means your dog will have plenty of attention, supervision, and companionship throughout the day. We have a large fenced-in yard for safe outdoor play and exercise. I also have two cats who grew up with dogs and are comfortable sharing their space, as well as two young children who have been around dogs their entire lives and know how to interact respectfully with them. For the comfort and safety of every pet in my care, I only accept dogs from one household at a time. This allows me to provide individualized attention and create a calm, stress-free environment during their stay. I understand how important it is to trust someone with your furry family member, and I will care for your dog as if they were my own. I look forward to meeting you and your pup! As a stay-at-home mom, I have a flexible schedule that allows me to provide attentive care throughout the day. My mornings typically begin with feeding pets, potty breaks, walks, or playtime before my family's daily activities start. Because I am home most of the day, pets receive frequent attention, supervision, and companionship rather than being left alone for long periods. Throughout the day, I can accommodate additional potty breaks, outdoor time in our fenced yard, feeding schedules, medication administration if needed, and plenty of affection and enrichment. In the evenings, pets are included in our family's relaxed routine, with more playtime, walks, and cuddles before bedtime. For boarding and daycare, dogs are rarely left unattended, and I only accept pets from one household at a time to ensure each pet receives personalized care and attention. I care for every pet as if they were my own, taking the time to learn their routine, preferences, and personality. I understand that being away from their family can be stressful, so I strive to provide a calm, safe, and loving environment where pets feel comfortable and secure. For dogs, I provide regular potty breaks, exercise, playtime, enrichment activities, and plenty of affection. Dogs have access to our large fenced yard for supervised outdoor time, and because I am home throughout the day, they receive consistent attention and companionship. I only care for dogs from one household at a time, which allows me to focus on their individual needs and maintain a low-stress environment. For cats, I ensure they have fresh food and water, a clean litter box, and attention at their comfort level. Whether your cat enjoys playtime, cuddles, or simply having a quiet and reliable caretaker, I respect their personality and routine. I am also comfortable following special instructions, administering medications when needed, and providing regular updates and photos so you can have peace of mind while you're away.

Sitter Profile Image: Kess S.
Verified Background Check
Kess S.
from
$15
per visit
5.0 out of 5 stars
28 reviews
8 repeat clients
15 years of experience
Indian River, Chesapeake, VA, 23325

Kess was amazing!! She took wonderful pictures and is very friendly! I am fully confident that she treated my dogs with the utmost care and love. I will be rebooking and would recommend her to anyone!

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Benjamin D.
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Over 1,569
pet parents in Chesapeake have booked pet sitting

Chesapeake pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Felecia was so awesome! Resun and Roxy absolutely love her I can tell and are very comfortable with her. They even let her bathe them lol. We appreciate her patience during the 2 meet and greets as well for she did not have to do that. She took great care of our home EVEN washed their dog bowls out🫂☺️ We are grateful to know her and be able to travel freely now without worry. Thank you Felecia! See you again soon

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LaStashia L.
Drop-In Visits
5.0 out of 5 stars

Jordan was amazing with my bulldog and chickens! She was very thorough with her care for Benny, and was able to administer all of his supplements and medications. I will trust her to come back in my home again.

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Michelle S.
Drop-In Visits
5.0 out of 5 stars

Hannah responds quickly to requests and is very attentive to details, which is great for pets with lots of hygiene/med instructions. She kept me posted regularly throughout her stay so I always knew how my furries were doing.

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Megan W.
Drop-In Visits
5.0 out of 5 stars

Jaclyn was amazing with both of my cats, we have never left them with someone who wasn’t family or a close friend, but Jaclyn made us feel like our babies were in good hands the entire time. We will definitely be booking with her again when we go on trips in the future!

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Jada R.
Drop-In Visits
5.0 out of 5 stars

Charell was so amazing and accommodating we had some plans fall through at the very last minute and she had no problem extending the dates for me truly and awesome sitter and a life saver!

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Hope K.
Drop-In Visits
5.0 out of 5 stars

Beth was great, my dogs loved her and she communicated with us constantly. Will definitely book again.

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Sara H.
Drop-In Visits
5.0 out of 5 stars

Maggie is an amazing petsitter! Punctual and so caring, she played every day with my cat and took care of everything for her. I felt so relaxed being away thanks to her and I’ve already re-booked her for another time!

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susanna f.
Drop-In Visits
5.0 out of 5 stars

Tyler did a great job caring for our two dogs. He was punctual and sent photos. We will definitely use him again!

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Teresa V.
Drop-In Visits
5.0 out of 5 stars

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.

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Brea W.
Drop-In Visits
5.0 out of 5 stars

Brandon was great with Chloe! He was super communicative and took great care of her. I received photos and a report card every day. Definitely will be using him again!

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Robert M.
Drop-In Visits
5.0 out of 5 stars

Love booking Haley every time we go out of town. She is always very responsive, sweet, and reliable for our cat.

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Emma C.
Drop-In Visits
5.0 out of 5 stars

McKayla did a great job caring for my community cat, made sure the food was put out, sent helpful updates, and included pictures so I could see that everything was okay. I really appreciated her communication and reliability, especially since caring for a feral cat can be a little different than caring for an indoor pet. I would definitely recommend her and would book with her again.

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Carmen S.
Drop-In Visits
5.0 out of 5 stars

Lucia did a great job looking after my 2 kitties! She followed all my instructions I left behind & was communicative during drop-ins! She definitely eased my mind when we were traveling. We’ll be sure to look out next time for Lucia when needing a reliable and caring sitter! ☺️

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Jelise N.
Drop-In Visits
5.0 out of 5 stars

Kylie takes such great care of my sweet golden! He was nice and calm when I came home, I could tell he got plenty of loving and attention while she did her drop-in!

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Sarah S.
Drop-In Visits
5.0 out of 5 stars

Sarah Anne was very responsive and communicated well. Her photos were great! My cat seemed to like her, he would come to greet her at her car, and was relaxed and in good form when I returned. Many thanks for her help!

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Catherine S.
Drop-In Visits
5.0 out of 5 stars

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!!

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Anthony S.
Drop-In Visits
5.0 out of 5 stars

Abi was a great sitter for my pitbull over a long weekend. She provided updates and took great care of her. I can tell she cares a lot about animals. We'd absolutely use Abi for drop in visits again. Thank you Abi!

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Lisa L.
Drop-In Visits
5.0 out of 5 stars

Top notch care for our 2 cats and 2 dogs! Loved the pics and reports! Will definitely call on Chelsea again! Highly recommended!🥳🩷

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Sandra M.
Drop-In Visits
5.0 out of 5 stars

Agnes took great care of my cat, she kept me updated the whole time and sent lots of pictures. 10 out of 10 I would ask her to watch my cat again

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C P.
Drop-In Visits
5.0 out of 5 stars

This was our 2nd time having Phoenix care for our 3 cats. She gave daily updates with pictures, and our kitties were happy, fed, and had clean litterboxes when we returned. I highly recommend.

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Laura G.
Drop-In Visits
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  1. 1. Search

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  2. 2. Meet & Greet

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  3. 3. Book & Pay

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The median cost per night for pet sitting in Chesapeake is $20

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Chesapeake average 7
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Chesapeake on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Chesapeake pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 600 pet sitters in Chesapeake. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 90% of Chesapeake pet sitters respond in under an hour.

Pet sitters in Chesapeake have an average of 20 years of experience. Pet sitters with repeat customers have an average of 7 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Chesapeake.

Rover makes it easy to find Chesapeake pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 600 pet sitters in Chesapeake on Rover, so you’re sure to find the perfect match for your pet! In Chesapeake, 100% of pet sitters offer daily exercise, 100% offer medication administration, and 100% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.