Pet Sitting & Drop Ins in Pleasant Grove West, Chesapeake, VA

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 Pleasant Grove West 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: Kristin O.
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Kristin O.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
94 reviews
26 repeat clients
14 years of experience
Pleasant Grove West, Chesapeake, VA, 23322

Thank you, Kristin, for the love, care, and attention you showered our kitties with! Our little rascals were happy and content when we returned home - what more could we ask for?! Thank you!

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Irina K.
Sitter Profile Image: Stephen s.
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Stephen s.
from
$15
per visit
5.0 out of 5 stars
82 reviews
29 repeat clients
30 years of experience
Great Bridge, CHESAPEAKE, VA, 23322

We've contact Stephen for last minutes Drop-ins and he's always able to help! Also, he's great with communication and send great pictures of his visit. Highly recommend.

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Jennifer P.
Sitter Profile Image: Anna A.
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Anna A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
153 reviews
49 repeat clients
7 years of experience
Chesapeake, VA, 23322

Anna is great! She’s been our go to since we have moved from Boston to Virginia a year + now. Great communication and very flexible schedule!

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Sharlett L.
Sitter Profile Image: Anna W.
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Anna W.
from
$21
per visit
5.0 out of 5 stars
3 reviews
8 years of experience
Great Bridge, Chesapeake, VA, 23322

Anna was great with Maui. I would definitely ask her again to watch my dog.

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Wallner S.
Sitter Profile Image: Jessica A.
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Jessica A.
from
$20
per visit
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
MOYOCK, NC, 27958

Jessica was very good to our four boys! She made sure to keep us updated with all the pictures and messages! She was also very accommodating with schedule changes!

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Arin O.
Sitter Profile Image: Emily F.
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Emily F.
from
$16
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
8 years of experience
Pleasant Grove West, Chesapeake, VA, 23323

Emily has been an excellent addition to our pups weekly routine. She is thorough and provides great feedback. Our pups are always happy to see her.

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Cerissa A.
Sitter Profile Image: Ani W.
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Ani W.
from
$14
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Chesapeake, VA, 23322

About: I absolutely love taking care of pets, especially dogs! I have a lot of energy to keep all dogs entertained. I have dog sitted before and absolutely enjoyed it. Seeing the dogs get excited when you show them the leash or even just show up is the best feeling ever! I try to get to know each dog as best as I can. If a dogs is super hyper and likes to go on runs, then I will do it. If a dog likes to walk at a slower pace, then we will walk at that pace. Each dog is special in their own way. I can also help clean any part of the house while watching over the dogs, if any help is needed. I am currently working during the week ( Monday- Friday) but I am free on anytime during the weekends. For Monday-Friday it just depends when you will need me and I can adjust. I can care for your pet in your own if they are more comfortable. Or I can have them in my own which has a fenced in yard.

Sitter Profile Image: Sabrina M.
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Sabrina M.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
56 reviews
21 repeat clients
48 years of experience
Pleasant Grove West, Chesapeake, VA, 23322

Sabrina saved the day when my neighbor couldn't watch my dogs for a night. She followed directions to a T and the dogs seemed very happy when I got home later that night.

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Alison M.
Sitter Profile Image: Maria & Matthew R.
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Maria & Matthew R.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
43 reviews
9 repeat clients
30 years of experience
Great Bridge, Chesapeake, VA, 23322

About: We have a laidback style but attentive . We’ve taken care of playful puppies, calm senior dogs, and everything in between, following routines exactly as you tell us. We treat every dog like part of our own family. We also offer long-term stays, especially for military deployments, so your pet can stay safe and settled for as long as you need. We’re home full-time now since Matt works from home, so your pets will always have company. We have full availability during weekdays and weekends, and we’re happy to adjust to your pet’s routine. Our home is calm, clean, and pet-friendly. We have a fully fenced yard with cameras so dogs can play safely, and we’re always close by keeping an eye on them. If a pet needs their own space to feel comfortable, we have a separate area ready for that. We make sure every pet feels secure, relaxed, and cared for during their stay.

Sitter Profile Image: Olivia D.
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Olivia D.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
6 years of experience
Great Bridge, Chesapeake, VA, 23322

Olivia takes great care of our elderly dog and communicates extremely well, making the entire process a breeze.

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Cheryl E.
Sitter Profile Image: Maya N.
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Maya N.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
52 reviews
17 repeat clients
12 years of experience
Chesapeake, VA, 23322

Maya is amazing! I completely fumbled on scheduling Maya had to make an unexpected trip out to see my fur baby and she was more than willing to do so!! 10/10!

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Lucille W.
Sitter Profile Image: Ariel & Brian K.
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Ariel & Brian K.
from
$25
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
20 years of experience
Pleasant Grove West, Chesapeake, VA, 23322

Ariel and Brian are awesome! We felt so comfortable and confident with our pets in their care. Both the dog and cat took to them quickly and were well taken care of. Ariel and Brian went above and beyond with their communication and daily photos of the pets. I strongly recommend them and will use them again!

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Marilyn F.
Sitter Profile Image: Gracie F.
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Gracie F.
from
$15
per visit
15 years of experience
Great Bridge, Chesapeake, VA, 23322

About: I have plenty of experience taking care of dogs from Chihuahua‘s to German shepherds and have been a proud cat Mama for 15+ years. I love spending time with cats and dogs and I really enjoy taking dogs on walks to stay active. I’m pretty much free anytime. I’m working on opening up my own solo cleaning business so I’m making sure to schedule any pet care Monday through Saturday pretty much anytime. I don’t often take care of pets in my home usually just overnight visits and as long as the pet is OK with climbing up the stairs because I live in the upstairs apartment of my parents house whenever there’s an overnight need normally I’ll go over to the owner’s home and stay there

Sitter Profile Image: Lacey T.
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Lacey T.
from
$25
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Pleasant Grove West, Chesapeake, VA, 23322

About: What sets me apart is my hands-on experience and genuine love for both dogs and cats. I currently work with dogs regularly and have four cats and one dog of my own. I’ve also spent time as a foster for cats, so I’m familiar with a wide range of personalities and special needs. I’m comfortable administering medications, caring for senior pets, and providing lots of individualized attention and affection. Whether it’s playtime, quiet companionship, or sticking to special routines, I’m dedicated to making sure your pets feel safe, happy, and loved while you’re away I am free all day to focus on pet care. This schedule allows me to provide attentive playtime, walks, feeding, and cuddles without rushing. I’m fully available to give extra care and attention to your pets, making sure they feel happy and comfortable When caring for pets in their own home, I prioritize safety, comfort, and routine to help reduce any stress your pet may feel while you’re away. I follow your instructions carefully whether it’s feeding times, medication schedules, or favorite play activities and make sure the environment stays clean and secure. I respect your pet’s space and personality, moving at their pace to build trust and keep them happy. Regular updates help you feel connected, and I treat your home and pets with the same care and respect I would my own.

Sitter Profile Image: Katelyn L.
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Katelyn L.
from
$20
per visit
3 years of experience
Pleasant Grove West, Chesapeake, VA, 23322

About: Hi! I’m Kate — a reliable and active pet sitter and dog walker who treats every pet like family. I know how important it is to have someone you trust caring for your pet, and I take that responsibility seriously. I have experience with dogs of all sizes, temperaments, and energy levels. Whether your dog loves long walks, structured exercise, or just some relaxed companionship, I adjust my care to match their routine and personality. Safety, consistency, and positive interaction are always my priorities. I’m attentive to feeding schedules, medications, and special instructions, and I keep a close eye on behavior to make sure your pet stays comfortable and happy while you’re away. I also believe great communication matters — you’ll receive regular updates and photos so you always know how your pet is doing. If you’re looking for dependable care, thoughtful walks, and genuine attention for your pet, I’d love to help! Pet care fits very naturally into my daily and weekly routine. I’m able to plan my schedule around walks, drop-ins, and pet sitting to make sure each pet gets consistent attention and care. I prioritize punctuality and reliability, so walks and visits happen on time and aren’t rushed. I stay active day-to-day, which makes regular walks and outdoor time an easy part of my routine. I also build in flexibility so I can adjust for longer walks, additional playtime, or special care needs when required. Because I’m organized and communicative, pet care never feels like an afterthought — it’s a planned and important part of my schedule. This allows me to give each pet the time, attention, and consistency they deserve. Safety and trust are my top priorities when caring for pets, whether in my home or a client’s home. I always follow the pet’s established routine closely, including feeding, walks, medications, and any special instructions you provide. In a client’s home, I’m respectful of the space and make sure doors, gates, and leashes are secure at all times. I keep pets supervised, avoid unsafe situations, and use safe walking practices such as checking equipment before walks and staying alert to surroundings. I take time to understand each pet’s personality, comfort level, and boundaries so they feel calm and secure. I use positive reinforcement, patience, and consistency to build trust, especially with pets who may be shy or anxious. I also communicate clearly and consistently, providing updates and photos so you always know your pet is safe, comfortable, and well cared for.

Sitter Profile Image: Amanda S.
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Amanda S.
Star Sitter
from
$38
per visit
5.0 out of 5 stars
141 reviews
81 repeat clients
20 years of experience
Great Bridge, Chesapeake, VA, 23322

We love Amanda! You can tell how much she loves our little pup and sends the cutest updates on her while she visits. We’ve had her stay overnight as well as do drop ins and she’s sweet, professional, responsible and has a love for animals. We never worry when we have Amanda care for our Cookie Jo 💖

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Betsy S.
Sitter Profile Image: Jensen G.
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Jensen G.
from
$14
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
4 years of experience
Chesapeake, VA, 23322

About: I’ve taken care of numerous pets throughout my life. I have three of my own and they are all happy campers. All furry friends are welcome and will receive the best love and care. I am active duty Military that currently is working shift hours. My days change weekly but every other week is the same. During my off days I am more than available to care for any and all of your babies needs. I have a fenced in yard with an Aussiedoodle and Labradoodle. Both very friendly with high energy. I have an orange and white cat who is also very friendly to both other cats and dogs. I enjoy spending time outside so they get all the energy out that they need.

Sitter Profile Image: Allison T.
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Allison T.
from
$14
per visit
5.0 out of 5 stars
2 reviews
25 years of experience
Pleasant Grove West, chesapeake, VA, 23322

About: Ive have cared for many breeds of dogs, guard dogs, cattle dogs, senior dogs, puppies and cats! Ive been helping friends and family my whole life care and watch when needed to care for their pets. I’m available monday, wednesday, thursday from 11am-7pm. I can offer playtime and walks, as I build trust and clients. I hope to build your trust for overnight stays in the future. At this time Im focused on dog / cat walking for you and playtime. I would take your dog to a dog park to run around in a safe environment for them.

Sitter Profile Image: Tayla B.
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Tayla B.
from
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
8 years of experience
Pleasant Grove West, Chesapeake, VA, 23322

Tayla was amazing doing drop ins with my two dogs for a few months. She’ll be my go to if I need someone in the future!

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Christina M.
Sitter Profile Image: Kathleen & Jehu & Jennifer M.
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Kathleen & Jehu & Jennifer M.
from
$20
per visit
5.0 out of 5 stars
25 reviews
7 repeat clients
8 years of experience
Great Bridge, Chesapeake, VA, 23322

Very helpful to keep everything nice and orderly with my pup while away! Came home to a happy puppy :)

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Sierra M.
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Pleasant Grove West pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Emily is amazing and our girls love her! She provides exceptional care to them, and we love our photos she sends at each visit!

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Cerissa A.
Drop-In Visits
5.0 out of 5 stars

Emily has been an excellent addition to our pups weekly routine. She is thorough and provides great feedback. Our pups are always happy to see her.

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Cerissa A.
Drop-In Visits
5.0 out of 5 stars

Our girls love Emily! She has been very attentive, sent us great pics and did an excellent job of checking in with us.

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Cerissa A.
Drop-In Visits
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If you’re searching for a Pleasant Grove West 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.

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

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Pleasant Grove West.

Rover makes it easy to find Pleasant Grove West 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

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.