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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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.

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

“Indiana was fantastic. I needed a sitter last minute and so thankful Indiana was available. I could trust her with my two fur babies and in my home. She took pictures during her visits so I could see they were happy and well cared for when I was away. Your fur babies are in good hands!”

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Carey T.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$20
per visit
5.0 out of 5 stars
• 41 reviews
21 repeat clients
18 years of experience
Chester, VA, 23831

“Jessica has dropped by on my pupsters on two separate occasions, and I would trust her anytime I need some help. She always provides adorable updates and is communicative. The pups have a great time with her. I will book Jessica everytime if she's available!”

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Erin B.
Sitter Profile Image: Abby M.
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Abby M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 309 reviews
112 repeat clients
14 years of experience
Chester, VA, 23831

“I didn't worry about Max at all while I was gone! I knew he was in good hands. Abby sent pictures and updates with each visit and Max seemed to really enjoy her company.”

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Alexandria J.
Sitter Profile Image: Annabella C.
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Annabella C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
• 25 reviews
9 repeat clients
6 years of experience
North Chesterfield, VA, 23237

“Annabella was able to help with Elvis very last minute and she was so great and patient with him. Would absolutely recommend her, she was fabulous !”

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Ruby V.
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: Allejah K.
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Allejah K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 7 reviews
7 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 less than 10 minutes from home and have a flexible schedule that allows me to check in during my breaks for walks, playtime, and potty breaks. While I’m away, I use indoor cameras to monitor pets and ensure their safety and comfort. I’m fully available and home on weekends, so your pup will get plenty of attention, care, and activity throughout their stay. 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: Melanie K.
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Melanie K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 47 reviews
6 repeat clients
10 years of experience
Chester, VA, 23831

“Melanie was absolutely awesome. She was so helpful with all of my needs, and she had no problem at all helping me out with extra issues that came up! She was very responsive and asked great questions, and she did an amazing job engaging with my cats and playing with / taking care of them. I felt at ease knowing she was there to take care of them, and I can’t recommend her enough!”

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Andrew K.
Sitter Profile Image: Maryurith M.
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Maryurith M.
from
$20
per visit
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: Linda A.
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Linda A.
from
$32
per visit
5.0 out of 5 stars
• 22 reviews
4 repeat clients
30 years of experience
Chester, VA, 23831

About: After recently relocating from Dallas, I’m excited to bring more than 30 years of pet-care experience to my new community. Back in Dallas, I ran an in-home pet-boarding business for a full decade, caring for pets of every breed, size, and personality. Over the years, I’ve also fostered countless dogs through local rescue programs, helping shy, senior, and special-needs pups find their confidence — and their forever homes. However, my experience goes far beyond cuddles and playtime. I’m skilled at administering oral, topical, and injectable medications, and I'm comfortable caring for pets of all ages, from energetic puppies to aging companions who need a little extra TLC. I believe every animal deserves calm, consistent care that keeps their routine — and their spirits — steady while their people are away. I'm a writer/editor that works remotely, and I have a stay-at-home dog dad to hang with my personal fur kids while I'm away. Point is, I have the a ton of flexibility. I care for your pets just as YOU care for your pets. That is, you set their schedule (feeding, bedtime, play, etc.), and I carry it out while you're away.

Sitter Profile Image: Brooklynn B.
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Brooklynn B.
from
$30
per visit
5.0 out of 5 stars
• 7 reviews
3 repeat clients
10 years of experience
South Chesterfield, VA, 23803

“Brooklynn was amazing with my babies! Lots of play time and pictures. She was very communicative with me and gave them lots of loving. Highly recommend!”

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McKenzie B.
Sitter Profile Image: Morgan W.
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Morgan W.
from
$25
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
9 years of experience
Chester, VA, 23831

About: I have previously worked in a kennel at an animal hospital for 3 years, years of house sitting services along with pet care provided on Rover. I have had cats and dogs of my own (pitbull mix and beagle mix). My schedule is flexible to be able to provide pet care services. I'm available for mid-day walks or drop-in visits during 11-2 Monday through Friday. I do not offer pet care services in my home but can ensure to cultivate safety, trust, and respect while offering services in your home.

Sitter Profile Image: Layla H.
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Layla H.
from
$18
per visit
7 years of experience
Chester, VA, 23831

About: I’ve been taking care of animals since I was 11 and I have taken care of a bunch of different animals in that time. I’m currently unemployed looking for jobs so I’m all free! I will be available pretty often. I will be doing online school around October and will be asynchronous and online. I am available very often. I can stick to pet routines and any medication and dietary needs. I would sometimes be accompanied by my boyfriend who can be an extra eye.

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
23 repeat clients
18 years of experience
Petersburg, VA, 23803

“Highly recommend Monique. She really worked with my senior pup who is set in her ways. She has been patient every visit and FINALLY today my dog wagged her tail and licked Monique! Monique is really good with both of my dogs and is always dependable.”

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Heather T.
Sitter Profile Image: Kayce M.
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Kayce M.
from
$30
per visit
4.9 out of 5 stars
• 154 reviews
32 repeat clients
15 years of experience
Petersburg, VA, 23803

“Kayce communicated very well with me and took such good care of Tucker! She was prompt and on time with her visits and ensured to keep him busy the entire time she was there. I received many pictures that helped reassure me he was in great hands! We will definitely have Kayce come back in the future!”

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Deanna M.
Sitter Profile Image: Rebecca B.
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Rebecca B.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 47 reviews
19 repeat clients
20 years of experience
Chesterfield, VA, 23234

“This was our first booking with Rebecca, and it went great! She did two drop-ins with Zeus over the weekend. She was communicative and prompt, and provided updates with pictures and a summary of their time together. We look forward to working with her again in the future!”

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Heather S.
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!

Sitter Profile Image: Rangeen A.
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Rangeen A.
from
$45
per visit
4.9 out of 5 stars
• 44 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: Journei F.
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Journei F.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
• 9 reviews
5 repeat clients
7 years of experience
Richmond, VA, 23234

About: I’ve been taking care of pets for most of my life. My family and friends have always counted on me to care for our/their pets when needed. I have walked, bathed, fed, snuggled and played with them! I am a full time worker, five days a week, nine hours a day from 9AM to 6PM. And I also have a part-time job that I do on the weekends, but I am still open to any service I could possibly provide for you and your pet! I receive my part-time job schedule weekly schedule every Saturday, so communication is key. I will care for your pets in your home by providing them the care that they need, walks, runs, snuggles, playtime, you name it! If there is anything specific you want me to know or abide by please let me know and I will make sure you and your pet are left satisfied :)

Sitter Profile Image: Hailee C.
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Hailee C.
from
$23
per visit
4.8 out of 5 stars
• 32 reviews
12 repeat clients
10 years of experience
Fort Lee, VA, 23801

“Hailee did a great job taking care of our two 60lb+ dogs while we were out of town. Always on time and included a bunch of pictures during check ins :)”

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Logan B.
Sitter Profile Image: Elizabeth J.
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Elizabeth J.
from
$20
per visit
25 years of experience
Richmond, VA, 23234

About: My boy kitty passed away last year at 14 years old. He became very sick in his last 2 years so his care required daily shots, weekly vet visits. I became very proficient in giving pills by mouth as well. He was big and strong and didn’t like the vet or car rides so i learned how to best manage a very scared kitty. My mom had a senior dog who developed diabetes so I cared for him in my home for the last few years of his life. I gave him insulin shots twice a day and performed his medical care. I gave him meds by mouth and performed other care duties. I work part-time and am in school at ODU online so my hours are flexible. I live in the Richmond area and service a fairly wide range as I have my own reliable transportation. I prefer to pet-sit in the clients home as I have a cat myself. My grandma rescued hunting dogs, particularly hounds and beagles, when I was growing up, so I am safety minded when it comes to pets, especially ones who get scared easily.

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Pet parents share their Rover experiences - Windsor Hills

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5.0 out of 5 stars

Hana is amazing and took such good care of my pups during the drop in. I couldn't have asked for a better sitter for them and am so grateful for her services.

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Christine & Nick G.
Drop-In Visits
5.0 out of 5 stars

Indiana was awesome! She went above and beyond for our cat while we were away. Would highly recommend her!

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Basja S.
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

Absolutely wonderful sitter! She took such great care of Remy and Gimlet and went above and beyond while we were away. Her updates were thoughtful and reassuring, and it was clear how much she genuinely cared about them. We came home to happy cats and everything in the house taken care of. We would absolutely book her again!

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Kayla C.
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

We are repeat customers and Allison never disappoints! I know that my fur babies are in safe hands when Allison watches over them!

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Victoria A.
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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How to book pet sitting

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FAQs for Pet Sitting - Windsor Hills

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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 .

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 , which provides up to 25,000 in eligible veterinary care reimbursement.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a 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 .

sitters on Rover set their own , 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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