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
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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Sitter Profile Image: Nicholas S.
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Sitter Profile Image: Nicholas S.
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1. Nicholas S.

Dog whisperer or maybe just talker
Virginia Beach, VA, 23464
4.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
168 reviews
69 repeat clients
from
$16
per visit
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Nicholas was heaven sent! He helped me out so much when I didn’t know what I was going to do with my pup while a last minute thing came up at work!

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Sitter Profile Image: Amy L.
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Sitter Profile Image: Amy L.
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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
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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 ❤️.

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Sitter Profile Image: Stephanie G.
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Sitter Profile Image: Stephanie G.
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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
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Stephanie was awesome to my fur babies. She was super friendly, reliable, and a very kind person who genuinely cares about your pets. I will definitely rebook and recommend her to anyone.

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Sitter Profile Image: Skye M.
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Sitter Profile Image: Skye M.
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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
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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!!

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Sitter Profile Image: Tiffany M.
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Sitter Profile Image: Tiffany M.
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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
123 repeat clients
from
$13
per visit
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Tiffany did a great job with my two dogs even though one is very nervous with strangers. She made my first time using Rover easy and stress-free with her updates. Will definitely use again in the future.

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Sitter Profile Image: Bailee B.
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Sitter Profile Image: Bailee B.
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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
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Thank you for taking care of my 3 cats! You are awesome, I highly recommend!

Sitter Profile Image: Tyler F.
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Sitter Profile Image: Tyler F.
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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
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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: Jackson L.
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Sitter Profile Image: Jackson L.
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8. 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
146 reviews
47 repeat clients
from
$15
per visit
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FIVE STARS! Extremely thankful that Jackson was available on such short notice. I had hired a sitter that backed out on our booking agreement the last day of my trip. Jackson came over to to walk, feed, and comfort Maisy after she had been ditched for a majority of the day by her previous sitter. He calmed my nerves and kept in contact throughout the entire drop in. I'm hoping Jackson will be free the next time I leave town!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Spencer M.
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Sitter Profile Image: Spencer M.
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9. Spencer M.

Meoow wufwuff… they’ll understand!
Chesapeake, VA, 23323
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$20
per visit
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Spencer is fantastic! He was quick to respond to my initial inquiry and set up the meet and greet. He clicked well with my animals, even winning some of my more skittish babies. He even made time to let one of our cats spend a few minutes outside each day, which is his favorite thing. Can’t recommend Spencer enough!

Sitter Profile Image: Kess S.
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Sitter Profile Image: Kess S.
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10. 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
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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!

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Sitter Profile Image: Ashley P.
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Sitter Profile Image: Ashley P.
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11. 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
98 reviews
33 repeat clients
from
$20
per visit
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Ashley was amazing!!!! My pups absolutely loved her! I felt my dogs and my home were in good hands as soon as we met. She went above and beyond anything I would have expected. I highly recommend her and will certainly work with her again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jackie L.
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Sitter Profile Image: Jackie L.
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12. Jackie L.

Eat. Play. Love.
Indian River, Chesapeake, VA, 23320
3.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$15
per visit

About: Hey there – 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Geneive M.
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Sitter Profile Image: Geneive M.
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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
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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!

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Sitter Profile Image: Shayla W.
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Sitter Profile Image: Shayla W.
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14. 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 very loving towards dogs. She consider her dog Apollo as another one of her children. He is very well trained by her and she shows us how to deal with him so he gets trained the same way by everyone. I would reccomend her as a dog sitter, your pet would be taken care of very well.

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Sitter Profile Image: Alyssa M.
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Sitter Profile Image: Alyssa M.
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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
66 repeat clients
from
$22
per visit
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Alyssa always goes above and beyond for our cat. Professional and clearly loves animals. Will always ask Alyssa to look after our furball family!

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Sitter Profile Image: Erin M.
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Sitter Profile Image: Erin M.
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16. Erin M.

Here for your pet-sitting needs!
Norfolk, VA, 23510
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$15
per visit

Erin was great house sitting our two dogs. She played with them, walked them, took care of them. And they loved her. I would recommend her without any hesitation and will use her again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Rodney B.
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Sitter Profile Image: Rodney B.
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17. 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

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.

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Sitter Profile Image: Reimsy A.
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Sitter Profile Image: Reimsy A.
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18. 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
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Reimsy looked after my cats while we were away. First time using Rover and Reimsy did amazing! Would definitely book her again if we go out of town!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kelsey W.
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Sitter Profile Image: Kelsey W.
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19. 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

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Sitter Profile Image: Jasmine R.
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Sitter Profile Image: Jasmine R.
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20. 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.

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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.

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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.

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