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

1. 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
166 reviews
68 repeat clients
from
$16
per visit
Profile image

During a tough time in our life we were able to not worry about our dogs, thanks to Nicholas! He is amazing with my tough husky and fabulous with my German Shepard.

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
9 reviews
5 repeat clients
from
$18
per visit
Profile image

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

3. 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
Profile image

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

4. 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
35 reviews
16 repeat clients
from
$20
per visit
Profile image

We booked Skye for a last minute, five-day trip during the holidays…it was our first time using Rover and we were all a bit nervous! Skye was compassionate, reliable, and very communicative…. I really can’t recommend her enough! She is amazing!!

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
396 reviews
122 repeat clients
from
$13
per visit
Profile image

Sadie, Cooper and Maddox loved their time with Tiffany. This visit was our first time ever leaving them in the care of anyone they didn’t know. All went very well and we will call on Tiffany again in the future. On a different note, I found navigating the website challenging and had difficulty choosing my dates to be gone. I was planning to be gone 3 days and thought I had it but only had the 1st and 3rd day. How terrible that would have been for my dogs! No food,water or medicine for my dogs. Tiffany to the rescue. I contacted her and she helped resolve the issue.

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

6. 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
Profile image

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

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

7. 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
Profile image

Kess was so great!! She was always on time and stayed engaged with my dogs the whole visit. She sent lots of great pics and videos of them playing and relaxing together. You can tell she loves this because she stayed even longer than expected!

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

8. 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
Profile image

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

9. 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
Profile image

Kelsey was absolutely wonderful to our two boys! Aside from the feedings and litter scooping, she took the time to ensure they were comfortable around her and even cleaned up a vase that the menaces had knocked over during the week. She sent us tons of pictures during visits too which really helped put us at ease. Thank you again for all you did for our boys - we will definitely be reaching out again for future bookings!

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
32 repeat clients
from
$20
per visit
Profile image

Ashley did an awesome job taking care of Shadow. Friendly and fun and willing to play to keep my dogs mind active during her time with him. Overall very responsive and respectful.

Sitter Profile Image: Shayla W.
Verified Background Check
Sitter Profile Image: Shayla W.
Verified Background Check

11. Shayla W.

Dog Lover
South Norfolk, chesapeake, VA, 23324
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$13
per visit

Shayla is great with pets. Especially dogs. She loves them and takes good care of them. I would definitely recommend her as a dog sitter.

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

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

13. 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
185 reviews
75 repeat clients
from
$20
per visit
Profile image

Geneive was fantastic! She kept me posted on when she arrived, and sent photos of my dog during the stay. She put my mind at ease and I knew my dog was in great hands.

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

14. 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
Profile image

Our 1st experience with Rodney was outstanding. Rodney cared for our 3 cats, fish and plants for 9 days. Our animals and our home were in great condition when we returned. Rodney sent photos and updates from each visit which was so reassuring. Rodney is a very warm and pleasant person and we look forward to booking with him for our future travel.

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

15. 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
186 reviews
67 repeat clients
from
$22
per visit
Profile image

Alyssa was wonderful! Even when she wasn't feeling well, she still came by to look after my cat. I loved that she worked with me as far as pricing goes. She even bought over a new cat toy and a new scooper!!! Alyssa is very sweet and I HIGHLY recommend her!

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

16. 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
Profile image

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!!

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

17. 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: Cameron D.
Verified Enhanced Background Check
Sitter Profile Image: Cameron D.
Verified Enhanced Background Check

18. Cameron D.

Local medical student and pet lover
Norfolk, VA, 23510
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
4 reviews
4 repeat clients
from
$14
per visit
Profile image

Amazing with my fur baby and super patient and understanding and very communicative. Will definitely rebook again for my cat drop ins while I travel!!!

Sitter Profile Image: Jasmine R.
Verified Enhanced Background Check
Sitter Profile Image: Jasmine R.
Verified Enhanced Background Check

19. Jasmine R.

Friendly and Compassionate
Chesapeake, VA, 23324
1.1 mi. away
Drop-In Visits, Dog Walking
2 reviews
from
$20
per visit

There is no one more reliable than Jasmine. She's very easy to reach and has a flexible schedule. I couldn't think of a better person as a caregiver, being that she pays attention to the details when doing a job.

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

20. 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!

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