Doggy Day Care in Windsor Hills

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Top rated Windsor Hills 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: Rikki G.
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Rikki G.
Star Sitter
from
$25
per day
5.0 out of 5 stars
25 reviews
16 repeat clients
39 years of experience
Colonial Heights, VA, 23834

Cairo had such a great time at his sitter. He was trying to go back in the house when I picked him up. He played alot and slept great that night.

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Christy N.
Sitter Profile Image: Abby M.
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Abby M.
Star Sitter
from
$28
per day
5.0 out of 5 stars
282 reviews
97 repeat clients
14 years of experience
Chester, VA, 23831

Very genuine person, got down on brownie's level to engage with her, brownie was happy and well taken care off. Abby worked with me and my schedule, I am grateful that brownie has a home away from home

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Tricia D.
Sitter Profile Image: Amanda B.
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Amanda B.
Star Sitter
from
$38
per day
5.0 out of 5 stars
18 reviews
5 repeat clients
20 years of experience
Chester, VA, 23831

Amanda is hands down a five-star sitter! She watched my dog all day and did an incredible job managing her high energy; she really went above and beyond to get all those "zoomies" out, and I picked up a very happy, tired pup. Her communication was also top-notch throughout the day, which gave me total peace of mind while I was away. If you’re looking for someone reliable who truly knows how to engage with dogs, I highly recommend booking with Amanda!

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Jennifer S.
Sitter Profile Image: Jeanette A.
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Jeanette A.
from
$27
per day
5.0 out of 5 stars
10 reviews
1 repeat client
30 years of experience
Chester, VA, 23831

Jeanette was great! She was able to accommodate Romeo in a very short time frame, and had to wake up early for the drop off. She kept me updated and Romeo loved her! Overall great experience.

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Felix L.
Sitter Profile Image: Royal & Rhonda P.
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Royal & Rhonda P.
from
$35
per day
5.0 out of 5 stars
158 reviews
50 repeat clients
5 years of experience
Chesterfield, VA, 23237

Phoebe LOVES going to daycare every week; I think she’s starting to learn which day it’s on. She’s been gaining confidence, learning new skills, and making friends while I’m at work, and I’m so grateful I found y’all!

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Megan G.
Sitter Profile Image: Deven & Tyreek C.
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Deven & Tyreek C.
Star Sitter
from
$27
per day
5.0 out of 5 stars
24 reviews
13 repeat clients
15 years of experience
North Chestefield, VA, 23237

Deven and Tyreek took amazing care of Birdie! I could tell Birdie had a truly amazing time being boarded and always looked forward to returning to such a loving home! Will definitely book their services again if in the area.

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Laura K.
Sitter Profile Image: Andrea B.
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Andrea B.
Star Sitter
from
$30
per day
5.0 out of 5 stars
25 reviews
6 repeat clients
4 years of experience
Chester, VA, 23831

My puppy loves her!

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Teja T.
Sitter Profile Image: Christine & Nick G.
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Christine & Nick G.
Star Sitter
from
$28
per day
5.0 out of 5 stars
54 reviews
19 repeat clients
20 years of experience
south chesterfield, VA, 23803

Christine and Nick are absolutely incredible with our German Shepherd, Aurora. This was her first time staying away from home and socializing with other dogs, and they made her feel completely safe, loved, and part of the family. They followed her routine, handled her quirks with confidence and compassion, and kept us updated the entire time. Aurora always comes home exhausted, happy, and clearly well cared for. We’re so grateful to have found such trustworthy and experienced sitters— Highly recommend!

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Erin M.
Sitter Profile Image: Ellysia F.
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Ellysia F.
Star Sitter
from
$27
per day
5.0 out of 5 stars
4 reviews
2 repeat clients
20 years of experience
Colonial Heights, VA, 23834

About: We love our fur babies and have been fostering dogs and cats for years. Every dog becomes a member of our family while they are here! Our furniture is pet-friendly and we have a fenced in back yard. We love to go to the park and hike with our dogs when the weather is pleasant! 🐾 Health & Vaccination Policy 🐾 For the safety and well-being of all pets in my care, I require that all dogs are up-to-date on the following vaccinations: • Rabies • DHPP (Distemper, Hepatitis, Parvovirus, Parainfluenza) • Bordetella (kennel cough) Puppies must have completed their full vaccination series appropriate for their age. I may request proof of vaccinations prior to your booking, especially for boarding or daycare stays where pets may be in shared spaces. Additionally: • Dogs should be free of fleas, ticks, and any contagious illnesses • Please let me know if your pet has recently been sick or exposed to illness • Pets showing signs of illness (vomiting, diarrhea, coughing, etc.) may need to reschedule for everyone’s safety I truly care about creating a safe, clean, and stress-free environment for every pet. Thank you for helping me keep all my furry guests happy and healthy! 🐶💛 I have plenty of free time to play with your pets, as I work from home part time. We love walks, so a well behaved dog is always welcome on our walks with us. The children in my life are also dog lovers and will be happy to snuggle, play and dote on your fur baby, too. I have a fenced in yard, a pet friendly home and I have a large crate, if needed. For anxious dogs, I have the space to keep your fur baby apart from other animals in my home.

Sitter Profile Image: Kendra B.
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Kendra B.
Star Sitter
from
$23
per day
5.0 out of 5 stars
38 reviews
9 repeat clients
25 years of experience
North Chesterfield, VA, 23237

About: What sets me apart is 25 years of experience. I began pet sitting at the age of 10 and have been surrounded by dogs my entire life. Providing pets with a safe, loving, and comfortable environment has always been a passion of mine. Including walking, bathing, and working with both puppies and senior dogs. I also have experience with pet sitting more than one dog. I currently volunteer remotely for two hours once a week, so I have plenty of free time to care for your fur baby. I'm available Monday through Friday, but I'm happy to be flexible if you need weekend boarding or doggy day care for your fur baby. I have a fenced yard and a friendly small dog who would love to keep your fur baby company. If you prefer, I can also crate your dog with ease.

Sitter Profile Image: Matt M.
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Matt M.
Star Sitter
from
$35
per day
5.0 out of 5 stars
269 reviews
84 repeat clients
25 years of experience
Northern Barton Heights, Richmond, VA, 23222

Matt is amazing !! I moved to Richmond for work for 13 weeks and he has made my life easier taking care of my 1 year old puppy, Paige. His dog, Cooper is super super sweet. And Paige comes home exhausted from all the fun she has had ! Very grateful for Matt’s help

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kelly k.
Sitter Profile Image: Cindy T.
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Cindy T.
from
$32
per day
5.0 out of 5 stars
301 reviews
82 repeat clients
20 years of experience
north chesterfield, VA, 23235

Eddie had a blast with Cindy!! She sent us so many pictures and updates that made us able to enjoy our time away from him and know he was being well loved. She was very accommodating with pick up and drop off as well. We can’t wait to use her again!

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Abbie S.
Sitter Profile Image: Cindy E.
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Cindy E.
from
$30
per day
5.0 out of 5 stars
2 reviews
2 repeat clients
14 years of experience
South chesterfield, VA, 23803

We had such a great experience with our sitter through the Rover app. She was incredibly accommodating and adjusted seamlessly to our schedule, which made the entire process smooth and stress-free. From the moment Tilley arrived, it was clear she genuinely cared for her like one of her own pets. She kept me updated, made sure Tilley was comfortable, and gave her so much love and attention during her stay. Her home had more than enough space for Tilley to feel relaxed and active, and I really appreciated how intentional she was about keeping her engaged with daily activities and playtime. Tilley came home happy, well cared for, and clearly enjoyed her time there. It gave me real peace of mind knowing she was in such good hands, and I would absolutely trust her to watch Tilley again in the future.

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Precious S.
Sitter Profile Image: Allejah K.
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Allejah K.
Star Sitter
from
$26
per day
5.0 out of 5 stars
6 reviews
5 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

About: What sets me apart is my calm, low-stress home where I host max 2 compatible dogs at once. Perfect for anxious, selective, or reactive pups who need peace over chaos. I also offer solo-stay pricing for dogs who need to block my second spot. My experience shines with senior dogs (gentle mobility support, meds) and high-energy mediums (structured play without overwhelming them). I work from home so I'm very flexible. I'm available during the day for walks/drop-ins/daycare, evenings/weekends for boarding. Dogs are family here; my routine revolves around their comfort. I don’t have any pets of my own currently. I have a nice size fenced yard and I love taking pups on long walks in my neighborhood or at the local dog park if possible. You can also book my backyard on Sniffspot!

Sitter Profile Image: Nadia J.
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Nadia J.
Star Sitter
from
$32
per day
5.0 out of 5 stars
35 reviews
14 repeat clients
10 years of experience
Randolph, Richmond, VA, 23220

If I could give her 10 stars I would!!! My Lily had such a great time. I really appreciated the tour of where she would be the dogs she will be around before leaving her. I felt very comfortable with leaving her there. I will absolutely use Nadia again and again ⭐️ ⭐️ ⭐️ ⭐️ ⭐️

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Ayesha D.
Sitter Profile Image: Julie W.
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Julie W.
Star Sitter
from
$27
per day
5.0 out of 5 stars
71 reviews
13 repeat clients
30 years of experience
Carillon, Richmond, VA, 23221

This was Luna’s first day with Julie. She was happy when I picked her up and seemed to enjoy herself. We have another day scheduled in a week.

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Ashley R.
Sitter Profile Image: Zach K.
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Zach K.
from
$32
per day
5.0 out of 5 stars
8 reviews
3 repeat clients
9 years of experience
Reedy Creek, Richmond, VA, 23225

About: I have owned and taken care of dogs, cats, and other pets for many years now. I thoroughly enjoy their company, and they seem to enjoy mine as well. I am very energetic and love spending time outside. As a carer for dogs, I believe strongly that they should get a ton of out door exercise. If you choose me as a care provider, you can be assured that they will be very active during their time with me, and location and temperament permitting, will have plenty of fresh air and green space to enjoy. In addition to loving on pets professionally, I work remotely from home as a grant writer. I make my own schedule, and can easily make time to get some fresh air. I live very close to Forest Hill Park, and spend lots of time there and the Buttermilk trail with and without dogs to walk. If you live elsewhere, I'll be exploring the green spaces near you with your dogs, and treating your personal space like the guest I am.

Sitter Profile Image: Lisa C.
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Lisa C.
Star Sitter
from
$34
per day
5.0 out of 5 stars
69 reviews
21 repeat clients
40 years of experience
North chesterfield, VA, 23237

Lisa was an absolute gem of a dog sitter! Her bubbly personality immediately put both me and my dogs at ease. She was incredibly generous with her communication, sending me regular updates and photos of their daily adventures, which I truly appreciated. It was so clear from every interaction that she has a genuine love for canines. I'd highly recommend her to anyone looking for a reliable and loving sitter.

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Kiana K.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$35
per day
5.0 out of 5 stars
44 reviews
10 repeat clients
15 years of experience
Chester, VA, 23831

Sabrina was extremely accommodating as I needed day care coverage extremely last minute. She allowed the my pup & her dogs to get comfortable with one another and sent me updates throughout the day without prompting. I truly appreciate her kindness and expertise and will definitely book with her again.

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Nay L.
Sitter Profile Image: Alana E.
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Alana E.
from
$30
per day
4.8 out of 5 stars
18 reviews
2 repeat clients
20 years of experience
Petersburg, VA, 23805

About: I grew up with many dogs of all sizes and personalities — from calm seniors to hyper puppies — and we also fostered animals growing up. Before having children, I worked at a doggy daycare, where I learned to care for multiple pets at once. Currently, my husband and I board for family and friends, and we’re excited to expand our care to more pets because we truly love animals! I am a stay-at-home wife, so your pets will have someone at home with them throughout the day giving attention, cuddles, and care. My husband works outside of the home, but he’s happy to help and loves animals too! We have three kids (infant to 8 years old) who absolutely adore animals, and we welcome both dogs and cats of all personalities. While our 2.5-acre yard isn’t fenced, we have a dog trolley system that allows pets to safely explore and enjoy the outdoors while leashed. We also love walks, playtime, and games of fetch for dogs who enjoy daily exercise. With us, your furry family members will receive lots of love, attention, and supervision throughout the day! I’m a stay-at-home mom, so she’s available to care for pets throughout the day. My husband is home outside of my work schedule, so together we can provide attention, supervision, and love for your dog or cat almost all day. Safety: Your pet’s safety is our top priority. While our 2.5-acre yard isn’t fully fenced, we use a dog trolley system that allows pets to safely roam and explore while remaining leashed. Inside the home, pets are supervised at all times. Trust: We treat every pet like family, providing attentive care, consistent routines, and regular updates so you can feel confident while you’re away. Environment: Our home is loving, calm, and kid-friendly, with plenty of space for pets to play, rest, and feel comfortable. We welcome dogs and cats of all sizes and personalities.

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Over 4
pet parents in Windsor Hills have booked doggy day care

Windsor Hills dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Rikki was understanding and accommodating on short notice. Rikki took great care of Phil and he had a lot of fun.

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Anh T.
Doggy Day Care
5.0 out of 5 stars

She treated my animals as if they were her own. My cat gave her a hard time, but she handled it like a champ! Would recommend her services!

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Vodrick
Doggy Day Care
5.0 out of 5 stars

We had such a great experience with our sitter through the Rover app. She was incredibly accommodating and adjusted seamlessly to our schedule, which made the entire process smooth and stress-free. From the moment Tilley arrived, it was clear she genuinely cared for her like one of her own pets. She kept me updated, made sure Tilley was comfortable, and gave her so much love and attention during her stay. Her home had more than enough space for Tilley to feel relaxed and active, and I really appreciated how intentional she was about keeping her engaged with daily activities and playtime. Tilley came home happy, well cared for, and clearly enjoyed her time there. It gave me real peace of mind knowing she was in such good hands, and I would absolutely trust her to watch Tilley again in the future.

Profile image
Precious S.
Doggy Day Care
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  3. 3. Book & Pay

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The median cost per day for doggy day care in Windsor Hills is $35

Why Choose Rover?

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    It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Windsor Hills average 4
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 Windsor Hills on Rover as of Jun 2026 was about $35 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 Windsor Hills 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, 604 sitters provided doggy day care in Windsor Hills. 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, 87% of Windsor Hills sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Windsor Hills have an average of 16 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 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 Windsor Hills.

Windsor Hills 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 Windsor Hills 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 604 sitters offering doggy day care in Windsor Hills on Rover, so you’re sure to find the perfect match for your dog! In Windsor Hills, 98% of sitters offer daily exercise, 96% offer medication administration, and 95% 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.