Pet Sitting Windsor Hills

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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Over 40
pet parents in Windsor Hills have booked pet sitting

Windsor Hills, Find top rated pet sitting

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

1 / 1
Sitter Profile Image: Indiana M.
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Indiana M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 52 reviews
19 repeat clients
15 years of experience
Chester, VA, 23831

“Indiana was phenomenal to work with. Took excellent care of our cats, was super respectful of our home and helped take care of a few things here and there in our house. Was also very communicative and let us know what was happening with our pets. 10/10 she’ll be our go to pet sitter whenever we are in need and she should be your go to as well!”

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Azmi K.
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 223 reviews
63 repeat clients
10 years of experience
Chester, VA, 23831

“Allison was so patient and kind with my senior dog Izzy : ) She went out of her way to do a meet and greet with my pup, and let her warm up at her own pace. I was able to be away for the day with confidence she was in good hands with Allison!”

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Jennifer R.
Sitter Profile Image: Darnell M.
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Darnell M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 102 reviews
39 repeat clients
14 years of experience
Colonial Heights, VA, 23834

“Darnell always takes such fantastic care of my pups and sends thorough and regular updates when he visits. It gives me great peace of mind knowing they are so well cared for! I highly recommend Darnell!”

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Julia M.
Sitter Profile Image: Phyllis N.
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Phyllis N.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 133 reviews
56 repeat clients
50 years of experience
North Chesterfield, VA, 23237

“Phyllis, AKA PJ, is awesome! We immediately liked her as soon as we met her. She’s so nice and personable and was great with our dogs. Willow, our goldendoodle, was immediately in love with her. She took great care of our 4 dogs and followed all instructions perfectly! We got photos and updates on time and knew that all our pets were well taken care of! We would 100% use PJ again!”

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Andrea H.
Sitter Profile Image: Meghan T.
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Meghan T.
from
$25
per visit
5.0 out of 5 stars
• 17 reviews
5 repeat clients
20 years of experience
Chester, VA, 23831

About: Hi! I’m Meghan. I’ve been around animals of all types my entire life. I have experience with farm animals, livestock, common house pets, birds, small rodents, and exotics. I have four dogs of my own, a pig, chickens, duck and conure! I would love to be able to give other pet owners peace of mind while they travel or take time off! I work full time during the day but have time in the afternoons beginning around 4pm for check ins, walks etc. My weekends are always free for walking, house sitting, and check ins. My pets are our family and they are treated as such. Yours will be too! I value those who care for my animals and take time to give them attention but respect house rules.

Sitter Profile Image: Lisa C.
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Lisa C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 71 reviews
22 repeat clients
40 years of experience
North chesterfield, VA, 23237

“First time meeting Lisa for a drop in visit with our dogs and she is great . Asked great questions regarding dog care and she interacted well with my dogs . Would use her again !”

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Kami J.
Sitter Profile Image: Maryurith M.
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Maryurith M.
from
$20
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
5 years of experience
Chester, VA, 23831

About: I’ve raised four German shepherds since they were nine weeks old and I will love and take care of your babies as I did mine! I’m currently working a full time job from Mon-Thurs from 7:30AM to 5:00PM. I have a routine of waking up before 4AM so I have plenty of time in the mornings, I am able to leave work between 11:30AM-1:00PM if I need to check on any pups at home or for potty breaks. I am off during the weekends, I don’t do much on my time off just read, clean and I try to exercise in my apartment. I live in an apartment and I will love to take walks and take your fur babies out when needed and for play time as well. I don’t have any pets at home. I will follow any instructions that you give me to sit your fur babies in my own home or yours.

Sitter Profile Image: Taevon M.
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Taevon M.
from
$20
per visit
15 years of experience
Chester, VA, 23836

About: I’m a caring and responsible pet lover who understands that every pet needs patience, attention, and a safe environment. I have experience caring for my own dogs and understand the importance of feeding schedules, walks, potty breaks, playtime, cuddles, and making pets feel comfortable. I’m attentive to each pet’s needs and will do my best to make sure your pet feels safe, loved, and well cared for while you’re away. I understand that every pet has a different personality and routine, and I will treat your pet with the same care and respect I would want for my own. I work a split shift job so during the day I have a lot of time to play and do walks. Your pup will have a good time. I have a dog play park in my area. We are also minutes away from a huge field. Your pup will have an amazing time.

Sitter Profile Image: Tyeir D.
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Tyeir D.
from
$13
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
20 years of experience
Chester, VA, 23836

“Tyeir took great care of my dog, she even remembered something I'd forgotten in my instructions. Very communicative and attentive to my dog's needs, highly recommend.”

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Bridgette T.
Sitter Profile Image: Abreya K.
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Abreya K.
from
$30
per visit
4.8 out of 5 stars
• 48 reviews
18 repeat clients
23 years of experience
Chester, VA, 23831

“Abreya did well with my cat.”

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Kiana D.
Sitter Profile Image: Michelle H.
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Michelle H.
from
$25
per visit
5.0 out of 5 stars
• 13 reviews
7 repeat clients
25 years of experience
Chester, VA, 23831

“Michelle was great with my dog. We met ahead of time and I felt great about having her drop in while we were away. My dog got the break he needed and some playtime and treats as well. I would definitely recommend Michelle and would rebook next time I need someone.”

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Amanda H.
Sitter Profile Image: Lashell D.
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Lashell D.
from
$35
per visit
5.0 out of 5 stars
• 32 reviews
6 repeat clients
15 years of experience
Chester, VA, 23831

“Lashell was great—prompt and excellent with communication. When Tut insisted on a short walk in the neighborhood, she was accommodating which was most appreciated. Will work with her again!”

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Christine H.
Sitter Profile Image: Monique & Daniel V.
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Monique & Daniel V.
from
$30
per visit
5.0 out of 5 stars
• 55 reviews
24 repeat clients
18 years of experience
Petersburg, VA, 23803

“Monique and family were great! Always on time as requested. They didn't just come to the house and feed our 5 dogs they actually took time with our dogs. Definitely recommend them to anybody!”

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Danny T.
Sitter Profile Image: Tianna L.
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Tianna L.
from
$28
per visit
4.5 out of 5 stars
• 8 reviews
2 repeat clients
5 years of experience
Courthouse, VA, 23832

About: I’ve taken care of my sisters dogs in the past, also owned many dogs growing up. My daughter LOVES them. My availability is pretty open! We would love to meet your furry friends. I’m in college and and i’m not currently working. My availability is open so that I will have plenty of time to care for your furry friend. We love animal's in my home we will treat them as our own of course. My place is clean and taken care of perfect setting.

Sitter Profile Image: Rangeen A.
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Rangeen A.
from
$45
per visit
4.9 out of 5 stars
• 46 reviews
14 repeat clients
10 years of experience
Richmond, VA, 23237

About: I am a former dog owner who's trained a few dogs. I will treat the dog like my own! I understand the importance of routine, exercise, and cuddles! I work full time. Mostly from home. My significant other has an alternative schedule so the dog would be under 24 hour supervision. I can't wait to have a buddy with me throughout the day! I understand how anxious your paw partner may be while you are away -- I am here to console your paw partner until you are back 💕 I live in a single home with a large fenced backyard with a pool they can play in! Great parks and trails nearby. Dogs will have freedom in all rooms of the home. Dog will be supervised 20-24 hours a day. This helps me ensure pet safety and quick turnaround on any changes to health and/or behaviors.

Sitter Profile Image: Sarah I.
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Sarah I.
Star Sitter
from
$45
per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
7 years of experience
Chesterfield, VA, 23832

About: I've been dog sitting since covid; things have changed but not the love for animals. Since my start I've dog sat for a wide varity of dogs. Puppies, oldies, big, small. Some requiring a lot of attention to help distract them, some that just sit by the door waiting for their pawrents to come home. From medications to special diets, specific schedules and give attention if you have the extra time. I will treat your dog as my own! Something you can count on is they will be loved and well taken care of. Pet care is my top priority. Making sure they are fed on time and they get plenty of play time and walks while you are gone. I unfortunately can't accept pets into my home as I don't currently live alone. But I'm more than willing to stay over whenever you need me to.

Sitter Profile Image: Danielle A.
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Danielle A.
from
$25
per visit
5.0 out of 5 stars
• 37 reviews
12 repeat clients
20 years of experience
Hopewell, VA, 23860

“Danielle is AMAZING! Took great care of our kitties and last minute! Think I found a new friend and someone to count on to take care of my fur babies while away! Ty Danielle!”

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Kimberly H.
Sitter Profile Image: Anna A.
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Anna A.
from
$45
per visit
5.0 out of 5 stars
• 11 reviews
1 repeat client
20 years of experience
Hopewell, VA, 23860

“Anna was great!! Bastian had a ball and he can be a handful. She handled his quirks beautifully”

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DAMACIA J.
Sitter Profile Image: Shannon O.
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Shannon O.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 66 reviews
29 repeat clients
20 years of experience
Chesterfield, VA, 23832

“Shannon did an awesome job on her drop-in visits with our three cats. Our home was also in great shape when we returned; all cat waste was handled properly. There is huge peace of mind knowing that our furkids are happy when we leave home.”

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Mary O.
Sitter Profile Image: Caitlyn W.
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Caitlyn W.
from
$20
per visit
5.0 out of 5 stars
• 13 reviews
2 repeat clients
20 years of experience
Chesterfield, VA, 23832

About: With a passion for animals that spans many years, a household full of furry companions, and a deep-seated love for our four-legged friends, rest assured that your pets are in safe hands. As a responsible adult equipped with both experience and a reliable vehicle, I'm committed to providing top-notch care and companionship for your beloved pets. I’m very flexible, work from home and am often available to move my schedule to match yours. I’m always happy to work together to make sure your lovely pets are taken care of I have two cats and two dogs of my own. Dogs are crate trained and both rescues that need a lot of love and I’m happy to provide. They enjoy walks and playing in our fenced yard. I also have two cats that love belly rubs and playing with their toys! My partner watches my animals while I take care of yours!

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The median cost per visit for pet sitting in Windsor Hills is $20

Pet parents share their Rover experiences - Windsor Hills

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5.0 out of 5 stars

Indiana is clearly passionate about working with animals. She seemed excited at the challenge of winning over my nervous pit mix, which made us feel like this was the right fit! I’m looking forward to Norma having a sitter that not only tolerates her, but loves and appreciates her as we do.

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Emily K.
Drop-In Visits
5.0 out of 5 stars

Hana was absolutely wonderful to have care for our fur babies! She was SO informative and shared photos of our girls while we were out of town. She made our time away so relaxing by her nice little write ups and updates! Will definitely book with again! Thank you!!

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Renessa Y.
Drop-In Visits
5.0 out of 5 stars

This was my second time booking Allison, and once again, she was absolutely wonderful! She is incredibly reliable, communicative, attentive, and genuinely thoughtful in everything she does. I especially appreciate her willingness to accommodate my booking on relatively short notice after I managed to mix up my vacation dates. Throughout the entire stay, she kept me updated, looked out not only for Psycho and her perpetually grumpy looking mother, but also kept an eye on the house and property, letting me know whenever something seemed out of place. What really stands out is her attention to detail and genuine concern for the animals’ well-being. She notices the little things, takes them seriously, and communicates proactively, which gives me tremendous peace of mind when I’m away. It’s a pleasure working with someone so dependable and conscientious. I couldn’t be happier with the care she provides, and I’ll absolutely be booking her again. Thank you, Allison!

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Tyler M.
Drop-In Visits
5.0 out of 5 stars

5 stars once again for Emily. I wish I could give 10! Emily is a wonderful pet sitter/drop in service. She is wonderful with our dogs and they love her and always pose for great pictures. If I say "Emily's coming!" they go crazy! We use Emily for both drop ins and long term housesitting. She is trustworthy, reliable, communicative, and most importantly, kind. Thank you so much Emily!!

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Alessia L.
Drop-In Visits
5.0 out of 5 stars

Would highly recommend Jen to look after your cat if you go out of town. She’s been looking after my cat for almost a year now, and she shows up on time and is very good about feeding and giving him water and scooping out his litter box. She’s very patient as well. My cat is very shy, and she was very patient and let him come up to her when he was ready. Now that he knows her, he loves her coming to look after him when I’m gone and loves it when she pets him and plays with him and scratches his ears.

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John P.
Drop-In Visits
5.0 out of 5 stars

Darnell is exceptional and I can’t thank him enough for all the care and love he gave our cat babies. This was the first time we used this service, and we will definitely use this service again. Darnell sent us pictures every day, two times per day, and he went above and beyond. We also received a report card with cute little notes about our furry children. Thank you Darnell!

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Jennifer H.
Drop-In Visits
5.0 out of 5 stars

Tiffany was a joy to work with. Great response time and punctual. She dealt well with our dog’s feeding requirements. Took very good care of our dog, and we really appreciated it.

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Renee P.
Drop-In Visits
5.0 out of 5 stars

Cassidy goes above and beyond for our cat and our house! We feel SO comfortable knowing that she's taking care of everything.

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Alex M.
Drop-In Visits
5.0 out of 5 stars

We love having Grace take care of our two cats. We like all the pics, they make us feel connected with the kitties back home.

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Diana W.
Drop-In Visits
5.0 out of 5 stars

We had a great experience with Jessica and will definitely use her anytime we need a cat sitter. We were away for 5 days and she took excellent care of our 8 cats (including two 4 month old kittens). Jessica was very communicative and kept us informed if anything happened. After every visit, she sent photos of each cat and gave a summary of how the visit went. It was obvious that she genuinely cared about our babies and was attentive to their individual needs.

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Jaryn C.
Drop-In Visits
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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

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

  • World-class support

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

How to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  2. 2. Meet In Person

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Popular requests for pet sitting - Windsor Hills

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Sitters in Windsor Hills average 7
repeat pet sitting clients

FAQs for Pet Sitting - Windsor Hills

Frequently asked questions about Rover

The average cost of Pet Sitting in Windsor Hills is $22 per visit as of November 2026. Most bookings cost between $18 and $31 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 2,541 sitters on Rover offering Pet Sitting across Windsor Hills. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.

Yes, you can find sitters who have experience with handling special pet needs in Windsor Hills. On Rover:

  • 90% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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