Doggy Day Care in Windsor Hills

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 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.

1 / 1
Sitter Profile Image: Jeanette A.
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Jeanette A.
from
$27
per day
5.0 out of 5.0 stars
7 reviews
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: Kendra B.
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Kendra B.
Star Sitter
from
$23
per day
5.0 out of 5.0 stars
19 reviews
4 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: Royal & Rhonda P.
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Royal & Rhonda P.
Star Sitter
from
$35
per day
5.0 out of 5.0 stars
150 reviews
46 repeat clients
5 years of experience
Chesterfield, VA, 23237

Rhonda agreed to watch Monroe last minute- convenient but also their family was kind and Monroe had a great time. Peaceful day relaxing with their dogs and family.

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Lorraine T.
Sitter Profile Image: Michael R.
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Michael R.
Star Sitter
from
$35
per day
5.0 out of 5.0 stars
51 reviews
25 repeat clients
6 years of experience
Petersburg, VA, 23805

Michael and his family took such good care of my pup. I got picture and video updates frequently. They were super flexible and accommodating to my short notice. Roni wore my girl out. I highly recommend this sweet family!

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Brooklynn B.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$35
per day
5.0 out of 5.0 stars
24 reviews
5 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: Ellysia F.
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Ellysia F.
from
$27
per day
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! 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: Lisa C.
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Lisa C.
Star Sitter
from
$34
per day
5.0 out of 5.0 stars
67 reviews
20 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: Amanda B.
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Amanda B.
from
$38
per day
5.0 out of 5.0 stars
3 reviews
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: Roxana M.
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Roxana M.
from
$30
per day
5.0 out of 5.0 stars
8 reviews
6 repeat clients
3 years of experience
Hopewell, VA, 23860

Our boys love coming here! Roxana is so patient and kind. The boys trust and love her and Starbuck.

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Jessi/ Josh D.
Sitter Profile Image: Allejah K.
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Allejah K.
from
$27
per day
5.0 out of 5.0 stars
4 reviews
2 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

About: Lifetime dog lover and caregiver with experience in geriatric care, allergy management, and weight control. Your furry-friends’ health and happiness will be my top priority. I work from home so I have the flexibility to work from your home and play and care for your furry friends, mid day walks, or even help with boarding needs. You can also book my backyard on Sniffspot! I don’t have any pets 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.

Sitter Profile Image: Abby M.
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Abby M.
Star Sitter
from
$28
per day
5.0 out of 5.0 stars
260 reviews
87 repeat clients
14 years of experience
Chester, VA, 23831

Abby, had great communication with me while our pup was there. She sent me pics which helped put our minds at ease. What sold me on her was that within 5 minutes of me reaching out with our dogs info and request for care she responded back with her address ready to take him immediately. If we’re ever in the area again we will definitely be using her services!

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Jessyca E.
Sitter Profile Image: Deven & Tyreek C.
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Deven & Tyreek C.
Star Sitter
from
$27
per day
5.0 out of 5.0 stars
14 reviews
7 repeat clients
15 years of experience
North Chestefield, VA, 23237

Deven, Tyreek, and Ozzy have been an amazing addition to Tonka's village. They are responsive, caring, and bring lots of joy to my pups life. I appreciate them immensely!

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Genarda B.
Sitter Profile Image: Sarah K.
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Sarah K.
Star Sitter
from
$43
per day
5.0 out of 5.0 stars
7 reviews
2 repeat clients
15 years of experience
Chester, VA, 23836

About: I promise you trust, communication, comfortability, and great care! I love pets! I grew up with a Golden Retriever named Skippy! I now own my beautiful mut mix of Lab, Pit and Blood Hound. His name is Maverick! He's 2 and such a loving, happy dude! I currently dog sit my mom's 3 Boston Terriors whenever she needs to go out of town and have been since I was a teenager. I also take in my best friend's older pit bull, Cookie, and her and Maverick get along wonderfully! There's plenty of space to walk dogs around my apartment community, along with a fenced in tennis court area where they can run free! I work full time AT HOME so I'm flexible just looking to make some extra money I work from home Monday through Friday, and am available most weekends, so I have lots of time and flexibility to care for your doggos! I live in an apartment but it's very dog friendly! I will ensure your dog gets lots of attention and love! I have access to lots of trails, open pet areas, and a fenced in tennis court where they can run free and we can play fetch! My dog is very friendly and has lots of experience around other dogs. I do have a large dog crate if that is required or necessary.

Sitter Profile Image: Cindy E.
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Cindy E.
from
$30
per day
1 repeat client
14 years of experience
South chesterfield, VA, 23803

About: Very loving and passionate about fur babies! We own a personal farm whom we take love and compassion to care for them! I have experience with home pets along with outside pets. i am a very active women who can keep up with any active pet. Looking forward to meeting new lovely fur babies! Available during the day, Monday through Friday. Can do some evenings and will also be available weekends depending on times client want the service done. Prefer to care in clients home, although could do at my house. We do own some land where they could roam while potty but as stated before, prefer to go in clients home.

Sitter Profile Image: Alana E.
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Alana E.
from
$30
per day
4.7 out of 5.0 stars
17 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.

Sitter Profile Image: Arlyn R.
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Arlyn R.
from
$40
per day
5.0 out of 5.0 stars
8 reviews
3 repeat clients
9 years of experience
Colonial Heights, VA, 23834

About: Hi, my name is Arlyn. I am 27 years old. I am born and raised in Honolulu, Hawaii and moved to Chester, Virginia back in 2011 but now living in Colonial Heights, VA. I'm a dog lover! I've owned 3 dogs previously and understand we want the best for them while we’re away. They are our fur babies after all right? I will make sure to give them lots of play time and walk time as well as sleep time. Making them feel at home and loved. Daily frequent walks are a must as well as play time. Even though you would be away, I wanna make sure they have a great time with me and help them feel less lonely. After all, mi casa es su casa (: Please remember to bring any dog bowls, food, leashes and any toys to make them feel at home and comfortable. In consideration, please bathe your furry one prior to house boarding or daycare. Thank you! Hope to see you soon! With current Covid regulations, I am permanently working from home so I am able to tend to your fur baby’s every need throughout the day. I have a 4 year old female pit bull & a 3 year old male bully that loves to play outside in our large fenced In back yard. They both have a crate that they can be in as well if your dog needs some separation. I can also crate your dog as well if needed.

Sitter Profile Image: Denny M.
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Denny M.
from
$40
per day
4.0 out of 5.0 stars
5 reviews
3 repeat clients
12 years of experience
Chester, VA, 23831

About: I’ve had recent pet care experience over the years with dogs and cats. I’ve watched family dogs and as well as some friend’s dogs and even cats. I’m currently unemployed so I have plenty of time to provide pet care on weekdays and weekends on afternoons and evenings if interested in booking I live in a pet friendly apartment complex with friendly residents that have dogs of their own. I will provide your pet with water, food, treats, attention and adventure

Sitter Profile Image: Abreya K.
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Abreya K.
from
$37
per day
4.8 out of 5.0 stars
47 reviews
16 repeat clients
23 years of experience
Chester, VA, 23831

Abreya is wonderful. Great communication, friendly, & flexible. Don’t hesitate to book her. We needed services early morning hours outside of her normal hours & she was able to do it. Communication was top notch. Definitely will be using her again & again. Thanks again Abreya.

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Tierney J.
Sitter Profile Image: Michelle H.
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Michelle H.
from
$35
per day
5.0 out of 5.0 stars
10 reviews
4 repeat clients
25 years of experience
Chester, VA, 23831

Thank you Michelle! You are awesome with my baby! There are more play dates in the future!

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Mona J.
Sitter Profile Image: Rangeen A.
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Rangeen A.
Star Sitter
from
$45
per day
4.9 out of 5.0 stars
34 reviews
9 repeat clients
10 years of experience
Richmond, VA, 23237

Rangeen is amazing!! I was coming through Richmond just for a day and she was so accommodating to my two pups, especially the timid not-so-dog-friendly one! Very responsive and kept me updated throughout their stay. If I lived closer, Rangeen would be our regular sitter! I hope we have the chance to book with her again.

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Ali S.
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Windsor Hills dog parents share their Rover experiences

1 / 1
5.0 out of 5.0 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
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

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

  • World-class support

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

Sitters in Windsor Hills 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 Windsor Hills on Rover as of Jan 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 Jan 2026, 544 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, 90% 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 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 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 544 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, 100% of sitters offer daily exercise, 98% offer medication administration, and 98% 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.