Doggy Day Care in Cheapside

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Top rated Cheapside doggy day care sitters

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

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Sitter Profile Image: Brandy G.
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Brandy G.
Star Sitter
from
$30
per day
5.0 out of 5 stars
104 reviews
38 repeat clients
30 years of experience
Buckroe, Hampton, VA, 23664

Brandy is an excellent dog sitter!!! I’m so grateful to have found her. She was quick to respond and immediately made me feel at ease. Milo went to her home for daycare and he did not want to leave! She played with him, took walks with him, and even did some obedience training. Milo came home tired and happy. She also sent photos and videos which always puts me at ease. I would highly recommend!

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Jessica S.
Sitter Profile Image: David P.
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David P.
Star Sitter
from
$35
per day
5.0 out of 5 stars
82 reviews
27 repeat clients
15 years of experience
Norfolk, VA, 23518

This was Bailey's first stay with David. Bailey had a great time playing with David's dogs and another that he was caring for. She came home very tired but happy. We will look to David for future visits when needed.

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Laura K.
Sitter Profile Image: Michelle J.
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Michelle J.
from
$35
per day
5.0 out of 5 stars
38 reviews
13 repeat clients
15 years of experience
Norfolk, VA, 23518

We contacted Michelle the morning we wanted daycare for our dog and she cheerfully responded within minutes. Michelle provided wonderful, loving care and was super at communicating. She sent 5 pictures and a video of her walking him during his stay. Her home was lovely and the neighborhood is great for walking. I highly recommend Michelle for daycare or boarding.

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Carol H.
Sitter Profile Image: Melissa G.
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Melissa G.
from
$30
per day
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Norfolk, VA, 23451

Melissa is PHENOMENAL!!! A truly caring and dedicated sitter!! She was patient and kind and understands how much our baby means to us. To say she went above and beyond is a huge understatement!! I wish I could hire her full-time! Her baby Pappy is a huge cherry on top!! We are so happy!!

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Marcela H.
Sitter Profile Image: Alexis F.
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Alexis F.
Star Sitter
from
$30
per day
5.0 out of 5 stars
5 reviews
2 repeat clients
4 years of experience
Downtown, Hampton, VA, 23669

Alexis was super flexible and was great with my pup! She sent pictures and kept me updated. I would definitely book with her again.

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Alissa H.
Sitter Profile Image: Gabriela R.
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Gabriela R.
Star Sitter
from
$30
per day
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Northwest, Virginia Beach, VA, 23455

About: Lifelong dog lover with 10+ years of experience from puppy stage to seniors, and medically involved dogs. I’ve trained and cared for many dogs of my own as well as others so I know how to adapt to each dog’s unique personality. For dog sitting, I can guarantee multiple walks a day, all the love, attention and play time your pup needs. Please let me know if your dog should be crated if I need to leave the house or if they are okay to free roam! I work remotely from home only leaving for a couple hours late morning. I am able to offer multiple walks a day along with all the attention! I have a small backyard partially fenced in for quick potty breaks but also live on a safe dead-end street in Chics beach that allows for great walks and adventures.

Sitter Profile Image: Michele H.
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Michele H.
Star Sitter
from
$30
per day
5.0 out of 5 stars
8 reviews
2 repeat clients
60 years of experience
Norfolk, VA, 23503

Michele was fantastic and my dog was so happy with her. She responded quickly and sent lots of wonderful updates of my happy dog. Will definitely be seeing her again for all my dog needs!

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Alexis W.
Sitter Profile Image: Hannah M.
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Hannah M.
from
$27
per day
5.0 out of 5 stars
8 reviews
1 repeat client
20 years of experience
Northeast, Virginia Beach, VA, 23451

About: I have experience with various dog breeds from pups-senior. I am very comfortable administering medications if needed. My labrador was AKC certified emotional support animal and I volunteered with him at several organizations in the area including with NAMI. I am competent in basic obedience training and behavior modification. I am currently working part time from home and will be home all throughout the week. Your pets will never be unattended longer than a couple of hours. I have a fenced yard fit for roaming, sniffing, and running but, better yet, I am located just feet from the First Landing state park trail and only a block from the beach. My home is set up to be pet friendly, your pets will love the comfy couches and beds.

Sitter Profile Image: Elisabeth F.
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Elisabeth F.
Star Sitter
from
$30
per day
4.9 out of 5 stars
193 reviews
58 repeat clients
20 years of experience
Hampton, VA, 23665

Elisabeth was prompt in her responses. Super flexible. The boys seemed great on pickup like they had a good time. Would definitely use her again and recommend her.

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Ryan H.
Sitter Profile Image: Cynthia J.
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Cynthia J.
from
$28
per day
5.0 out of 5 stars
30 reviews
5 repeat clients
35 years of experience
Northeast, Virginia Beach, VA, 23451

Cynthia was amazing! She responded very quick to my request and was very responsive when I messaged her. I’ll definitely continue to use to I have her watch my Chloe. Thank you Cynthia 😊

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Justin B.
Sitter Profile Image: Kim M.
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Kim M.
from
$22
per day
5.0 out of 5 stars
368 reviews
162 repeat clients
28 years of experience
Foxhill, Hampton, VA, 23669

Kim was awesome. My Lucy loved her husband and laying up on their couch. Kim was very accommodating and flexible for us. I would definitely use again.

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Shannon L.
Sitter Profile Image: angela a.
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angela a.
from
$30
per day
5.0 out of 5 stars
4 reviews
20 years of experience
Norfolk, VA, 23503

About: Over 20 years of being farm raised and understanding how to care for pets. Exceptional with routine, caregiving and listening to the details of your pet's care needs. I currently work from home and am available for early and late drop offs for your fur baby's daycare or overnight stay needs. Emergency situations also considered on a client by client scenario. The beach is my back yard and offers wonderful sights and sounds for your pet. Inside the home is quiet, and gentle so your little one feels safe and well cared for.

Sitter Profile Image: Jakorey W.
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Jakorey W.
Star Sitter
from
$30
per day
5.0 out of 5 stars
10 reviews
3 repeat clients
2 years of experience
Mercury Central, Hampton, VA, 23666

Jakorey was friendly and my sweet girl took to him quickly. The pictures Jakorey sent seemed like she was having fun. A+++ Sitter.

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Yolanda D.
Sitter Profile Image: Lisa W.
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Lisa W.
from
$25
per day
4.9 out of 5 stars
28 reviews
9 repeat clients
7 years of experience
Northwest, Virginia Beach, VA, 23462

Seems like Taz had a good time with very little stress and exercise. Thank you!

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Lowell H.
Sitter Profile Image: Robin P.
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Robin P.
from
$35
per day
5.0 out of 5 stars
10 reviews
3 repeat clients
5 years of experience
North King St, Hampton, VA, 23669

About: I’ve grown up with many animals in my home. Ranging from dogs, cats, birds, and reptiles. I know what it means to feel at ease knowing your pets are being well taken care of while you’re away. Let me be that person for you. Currently, I am a stay at home mom with one small child. Which makes my availability pretty flexible. I will try my best to work out our schedules so that your pets get all the attention they need. I do not view our pets as just pets. They are an extension of our family. Just as much a family member as any other. They deserve time, respect, and love. Nothing feels more rewarding than earning the love and trust of another animal. I strive to provide the best care for God’s beautiful creatures.

Sitter Profile Image: Julie & Kenneth N.
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Julie & Kenneth N.
from
$30
per day
5.0 out of 5 stars
150 reviews
58 repeat clients
10 years of experience
Norfolk, VA, 23505

I’m so happy to have found Julie. She’s a wonderful sitter and took really good care of my precious puppies. Will book with her again! Thank you, Julie!

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Eugenia A.
Sitter Profile Image: Bryan S.
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Bryan S.
Star Sitter
from
$33
per day
4.9 out of 5 stars
50 reviews
24 repeat clients
40 years of experience
Hayes, VA, 23072

This family takes great care of our pup. When I pulled into the drive and Rosy recognized where we were, she was super excited! They love her and Rosy loves them right back!

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Andrea R.
Sitter Profile Image: Tyrah J.
Tyrah J.
from
$27
per day
5.0 out of 5 stars
3 reviews
15 years of experience
Downtown, Hampton, VA, 23669

About: I have been caring for dogs since 2011 and have owned a variety of breeds, including Yorkies, Beagles, and German Shepherds. My dogs have always been beloved family members who lived long, happy lives. I understand the importance of dependable, loving care and will treat your pet with the same attention, patience, and affection I give my own. I work from home, which allows me to provide frequent attention, potty breaks, walks, playtime, and companionship throughout the day. Because I am home most of the time, pets in my care receive plenty of supervision, affection, and a consistent routine. I know every pet has their own routine, so I take the time to learn what makes them comfortable. Whether that means sticking to a specific feeding schedule, going for extra walks, playing fetch, or just relaxing on the couch, I try to keep their day as normal as possible. I work from home and have a fully fenced yard, which allows for plenty of supervised outdoor time, exercise, and play throughout the day. I also keep owners updated with photos and messages so they can feel confident their pet is happy, safe, and well cared for.

Sitter Profile Image: Melissa & Jeremy W.
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Melissa & Jeremy W.
Star Sitter
from
$30
per day
5.0 out of 5 stars
47 reviews
14 repeat clients
30 years of experience
Norfolk, VA, 23518

Melissa and Jeremy were excellent with my puppy. They were able to schedule and play day with him was short notice, and they followed all my expectations. My dog had a wonderful time with them and I will most definitely be scheduling another play date with them.

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Taurean W.
Sitter Profile Image: Dustin W.
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Dustin W.
Star Sitter
from
$32
per day
5.0 out of 5 stars
110 reviews
38 repeat clients
27 years of experience
Virginia Beach, VA, 23452

We left our puppy with Dustin for a few hours so he could get familiar with Dexter before we board with him. It was our first time leaving him with other dogs around and was a little nervous. There was absolutely no need! Dustin is great. You can tell he has a passion for dogs and is very professional. Dexter seemed to enjoy himself and was nice and tired! We feel very comfortable with Dexter staying with him while we are away for 3 weeks. Thank you Dustin.

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Laura T.
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The median cost per day for doggy day care in Cheapside is $30

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Sitters in Cheapside average 3
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Cheapside on Rover as of Jun 2026 was about $30 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Cheapside doggy day care sitter for the first time, visit the sitter’s profile and select the Contact button.

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

As of Jun 2026, 326 sitters provided doggy day care in Cheapside. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 83% of Cheapside sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Cheapside have an average of 17 years of experience. Sitters offering doggy day care with repeat customers have an average of 3 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Cheapside.

Cheapside doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Cheapside sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 326 sitters offering doggy day care in Cheapside on Rover, so you’re sure to find the perfect match for your dog! In Cheapside, 100% of sitters offer daily exercise, 97% offer medication administration, and 93% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

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

With Rover, you can find a trustworthy, loving pet sitter to take care of your dog while you're at work or have a day full or errands. 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 40,000 sitters who've listed their services on Rover. That way, you're sure to find a doggy day care who's right for your needs. We're proud that 95% of our sitters have 100% 5-star reviews, and we think your dog will love them too. Search for a sitter who offers doggy day care, schedule a Meet & Greet, and book the stay if it seems like a good fit. No matter how often you need day care, you're sure to find a sitter who will treat your dog like family.

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