Pet Sitting in Chesapeake

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Sitter Profile Image: Stephanie G.
Verified Enhanced Background Check
Sitter Profile Image: Stephanie G.
Verified Enhanced Background Check

1. Stephanie G.

Pet Sitting- There When You Need It
Greenbrier West, CHESAPEAKE, VA, 23320
4.8 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
7 repeat clients
from
$18
per visit

Stephanie was awesome with my two dogs. She let them out in the backyard and played with them for a bit. She’s reliable, responsible and the dogs love her!

Sitter Profile Image: Amy L.
Verified Enhanced Background Check
Sitter Profile Image: Amy L.
Verified Enhanced Background Check

2. Amy L.

Genuine Fur Baby Walker
norfolk, VA, 23517
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
5 repeat clients
from
$18
per visit

Amy was my life saver in a day were I couldn’t find anyone to check up on my Baby Chilli she was available and very communicative, goes the extra mile and sends lots of photos ❤️.

Sitter Profile Image: Skye M.
Verified Enhanced Background Check
Sitter Profile Image: Skye M.
Verified Enhanced Background Check

3. Skye M.

Vet Tech/Artist, Available Anytime!
Greenbrier West, Chesapeake, VA, 23320
4.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
16 repeat clients
from
$20
per visit

My first time using Rover and having Skye care for my crew. I’m very happy, I enjoyed getting pics and updates and will def be using Skye again.

Sitter Profile Image: Nicholas S.
Verified Background Check
Sitter Profile Image: Nicholas S.
Verified Background Check

4. Nicholas S.

Dog whisperer or maybe just talker
Virginia Beach, VA, 23464
4.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
162 reviews
67 repeat clients
from
$16
per visit

Nicholas was wonderful with my two Great Danes! He was so helpful & even sent pictures! I will definitely be booking with him in the future!!

Sitter Profile Image: Tiffany M.
Verified Background Check
Sitter Profile Image: Tiffany M.
Verified Background Check

5. Tiffany M.

Dog, Hamster and kid mom :)
Virginia Beach, VA, 23464
4.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
393 reviews
122 repeat clients
from
$13
per visit

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!

Sitter Profile Image: Jackson L.
Verified Enhanced Background Check
Sitter Profile Image: Jackson L.
Verified Enhanced Background Check

6. Jackson L.

BIG DOGS LITTLE DOGS OLD DOGS PUPS
Norfolk, VA, 23509
4.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
143 reviews
47 repeat clients
from
$15
per visit

This was our first time using a dog sitter, so we had our reservations at first but this was truly a great experience. Jackson did a great job and our dogs felt comfortable with him. It gave us peace of mind that our fur babies were taken care of while we were away.

Sitter Profile Image: Tyler F.
Verified Enhanced Background Check
Sitter Profile Image: Tyler F.
Verified Enhanced Background Check

7. Tyler F.

All breeds welcome! EVMS Student
Norfolk, VA, 23507
3.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
44 reviews
20 repeat clients
from
$20
per visit

For my first experience with this app, Tyler has exceeded my expectations. Very respectful and kind person who genuinely cares about your pet. Tyler took care of our dog as if it was his and I’m truly grateful for his service. 10/10 recommend! Thank you Tyler!

Sitter Profile Image: Kess S.
Verified Background Check
Sitter Profile Image: Kess S.
Verified Background Check

8. Kess S.

Enthusiastic Animal Lover!
Indian River, Chesapeake, VA, 23325
2.8 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
27 reviews
8 repeat clients
from
$15
per visit

Kess is just wonderful, and I highly recommend her to anyone looking for someone to care for your pet like her own while you’re away! She is detail oriented and patient. My cat, who is typically quite anxious, warmed up to her right away :) She also sends such lovely, detailed messages and cute photos. Will absolutely continue reaching out to her in the future for help when I’m away!

Sitter Profile Image: Bailee B.
Verified Enhanced Background Check
Sitter Profile Image: Bailee B.
Verified Enhanced Background Check

9. Bailee B.

Taking Pet Care to the Next Level!
Portsmouth, VA, 23702
3.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 reviews
11 repeat clients
from
$15
per visit

Thank you for taking care of my 3 cats! You are awesome, I highly recommend!

Sitter Profile Image: Ashley P.
Verified Background Check
Sitter Profile Image: Ashley P.
Verified Background Check

10. Ashley P.

Walks,Parks,Swimming,Friendship:YES
Norfolk, VA, 23517
3.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
95 reviews
31 repeat clients
from
$20
per visit

Ashley did a great service for us caring for our puppy,Holly. She wanted to accommodate caring for our puppy as if she was her own. We really appreciated her care! We would use her again and recommend her highly.

Sitter Profile Image: Jackie L.
Verified Enhanced Background Check
Sitter Profile Image: Jackie L.
Verified Enhanced Background Check

11. Jackie L.

Eat. Play. Love.
Indian River, Chesapeake, VA, 23320
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$13
per visit

About: Hey there – my name is Jackie, and I’ve taken care of dogs my whole life. I am an experienced sitter who you can trust to take amazing care of your pup. I take any (and all) opportunities to snuggle and go on fun adventures with dogs. Some people have told me I’m a dog whisperer at times… I have yet to prove them wrong. Thirty year old mom, wife, and USCG veteran, with 15+ years of experience caring for my own, and others, pets - including dogs, cats, and birds. I can administer oral or injected medication, and have experience with senior and special needs dogs. I will treat your babies like my own but will also respect their boundaries and strive to keep them as comfortable as possible. I am a schoolteacher - available Monday thru Friday after 2:30PM, open availability on the weekends, and totally free all summer to care for, walk, exercise, and love your babies. I am always in a constant state of supervision when watching other people's pets. It is second nature for me to ensure there aren't any hazards around that could harm your baby, just as I would expect for anyone watching my fur babes.

Sitter Profile Image: Shelby J.
Verified Enhanced Background Check
Sitter Profile Image: Shelby J.
Verified Enhanced Background Check

12. Shelby J.

Here to pamper your pet
Norfolk, VA, 23517
3.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$15
per visit

Shelby is awesome. 5 out of 5 stars. She definitely deserves it, she literally came in a clutch moment when an emergency came up with another sitter. She responded in a timely manner, no questions asked and took the task by the horns.

Sitter Profile Image: Kelsey S.
Verified Background Check
Sitter Profile Image: Kelsey S.
Verified Background Check

13. Kelsey S.

Passionate Animal Care Taker
Norfolk, VA, 23502
3.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
26 reviews
6 repeat clients
from
$13
per visit

Kelsey did a great good checking on our sweet cat. I thought she was going to be too shy to come out and visit but Kelsey got her out with the laser pointer and sent pics of them playing. We will absolutely request more visits with Kelsey in the future!

Sitter Profile Image: Alyssa M.
Verified Background Check
Sitter Profile Image: Alyssa M.
Verified Background Check

14. Alyssa M.

Rover 101
Little buddies new best friend!
Indian River, Chesapeake, VA, 23325
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
185 reviews
67 repeat clients
from
$22
per visit

Alyssa is fantastic! She watched my two cats while I was away for the week and kept me updated with cute photos and notes on how they were doing. They both seemed very happy! Also, she did a great job with taking care of their litter box and their food / water. I highly recommend her and will be using her again :)

Sitter Profile Image: Rodney B.
Verified Background Check
Sitter Profile Image: Rodney B.
Verified Background Check

15. Rodney B.

I'll care for your FurKid!
Indian River, Chesapeake, VA, 23325
2.3 mi. away
Drop-In Visits
5.0 out of 5 stars
23 reviews
12 repeat clients
from
$20
per visit

Very attentive to our dogs routines, and looked for ways to go above and beyond, like washing their dog bowls without even being asked. Our dogs loved him. 10/10 would hire him again.

Sitter Profile Image: Brianna F.
Verified Enhanced Background Check
Sitter Profile Image: Brianna F.
Verified Enhanced Background Check

16. Brianna F.

Will <3 your fur babies like my own
Norfolk, VA, 23517
3.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
14 reviews
6 repeat clients
from
$20
per visit

Brianna was WONDERFUL! We were new to the area and stressed about finding a new cat sitter. She exceeded our expectations and relieved so much anxiety! She went above and beyond to become familiar with our cats and make them as happy as possible during her visits. She gave great updates and lots of photos. Will absolutely be using her again!

Sitter Profile Image: Geneive M.
Verified Background Check
Sitter Profile Image: Geneive M.
Verified Background Check

17. Geneive M.

Energetic Family
Norfolk, VA, 23509
3.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
184 reviews
74 repeat clients
from
$20
per visit

Geneive was great with our kitty! He was not feeling like himself and had to get medications given to him and Geneive did a great job giving him his medications. She sent us many pictures and videos of him throughout the time. Its not easy leaving your sick pet with someone put she made us feel comfortable that our kitty was well taken care of. She was on time and professional. Will definitely use her again and recommend her to anyone!

Sitter Profile Image: Kelsey W.
Verified Enhanced Background Check
Sitter Profile Image: Kelsey W.
Verified Enhanced Background Check

18. Kelsey W.

I can’t wait to meet your animals!
Norfolk, VA, 23504
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
15 reviews
3 repeat clients
from
$16
per visit

As long as I’ve known kelsey he’s been great with animals and loves to be with animals all the time. He’s very caring and always wants to play with animals

Sitter Profile Image: Sophia H.
Verified Enhanced Background Check
Sitter Profile Image: Sophia H.
Verified Enhanced Background Check

19. Sophia H.

Sharing my love of dogs with dogs
South Norfolk, Chesapeake, VA, 23324
0.7 mi. away
Drop-In Visits, Dog Walking
2 reviews
from
$15
per visit

Sophia is the biggest dog lover I know! She’s got a heart of gold towards everyone she meets two legged and four. Whenever Im in a pinch Sophia is the friend I know I can always call. She’s the most reliable person you’ll ever meet! Thanks for all you do Sophia!

Sitter Profile Image: Reimsy A.
Verified Enhanced Background Check
Sitter Profile Image: Reimsy A.
Verified Enhanced Background Check

20. Reimsy A.

all dogs and cats are welcome!!
Portsmouth, VA, 23704
2.1 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
4 repeat clients
from
$14
per visit

Reimsy was absolutely fantastic!! She went over and above my expectations making sure to track down my shy guy and provide pictures to ease my mind as well as keeping me updated on how much he was eating. Reimsy was very flexible with my keys hand off (I only have 1 set). Will definitely be using her again!!

Search Map

Chesapeake Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Chesapeake are rated on average 5 out of 5 stars based on 1,043 reviews.

Check out the Pet Sitting & Drop Ins in your neighborhood:

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Chesapeake:


Rover.com is the simple, savvy way to find and book Deep Creek West-Dismal Swamp, Chesapeake house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Deep Creek West-Dismal Swamp on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes the Rover Guarantee, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Deep Creek West-Dismal Swamp, Chesapeake, VA house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

Drop-In Visits