Pet Sitting & Drop Ins in Windsor, Richmond, VA
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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Top rated Windsor pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Kyla did a great job looking after my cats. It was easy to set things up, she arrived as scheduled, communicated well throughout, and my cats liked her too.”


“This was our first time using Rover and we are so glad we found Jeffrey. He took such great care of our diabetic cat so we could rest easy on vacation.”


“Catherine was great!! She updated and sent pictures every time she stopped in. My one dog Va. be anxious around new people and she instantly made her feel comfortable. I was never worried the entire time I was away.”


“Maria and Luis are fantastic pet sitters. Even our very shy cat warmed up to them. We came home to happy cats who got care, play and love while we were away. We will certainly book with them again. Thank you Maria & Luis!”


“I’m never using anyone else! Tyler has a genuine love and passion for animals that shows in her visits and when she hosts. You won’t just get pictures of your dog playing in backyard - she actually spends time with your pup”


“Allyson is the best! I never worry about our dog when she is here!”


About: I’ve taken care of multiple breeds and of varying ages. I’ve also helped train my own puppy, as well as friends’ dogs, the basics like potty training, sit, etc. I’m quite comfortable with puppies under 1 year old all the way to our senior friends. I’m currently a full-time dog mom and pet caretaker. I just graduated from grad school and don’t start my new job until this fall, and I thought - what a better way to spend my summer off taking care of my favorite animal and helping other pet owners? I’m an open communicator and can be available how you need me with the proper heads-up! I live in an apartment building with my fiancé and our sweet, cuddly boy dog (neutered). There’s 3 parks within walking distance and a dog park just an 8min drive away. Since I live in an apartment, I would recommend only small to medium dogs stay with us, but I’m always willing to travel to clients’ houses for dogs of all sizes. I treat my clients dogs as if they were my own fur baby. The love, kindness, & attention I give my sweet boy is the same love, kindness, & attention your dog will receive. My friend is also a vet tech I can always reach out to for advice/questions and I myself am a certified (human) healthcare professional.

“Elle was great with Sake her first time! He went right to her during her care for him. She always left good information on my cards. I will definitely be asking her to help out again. Thank you so much Elle for taking care of Sake. We really appreciate it!!! ??”


“Andrew has been by far the best dog walker you could ask for. Always going above and beyond. He literally offered to install the portable AC in my house while I was at work and the AC went out. Leaving Richmond is going to be hard but finding anyone better with my dog will be impossible!”


“Abby is awesome! She took great care of our “senior” orange tabby 😽 We got great updates and photos every visit and felt great knowing our boy was in such good hands. Thank you such Abby!”


“Alexander was awesome! My silly, hyper pup warmed up to him well and he made sure my big oy was taken care of without any deviations from our routine. I will be planning on booking Alexander soon!”


“Kay took excellent care of my 2 cats and my outdoor tomato plants while I was away for a long weekend. Cats were chill and happy upon my return. Kay communicated with me frequently and quickly. I didn't feel like I had to worry about anything while I was away.”


“Claire was FANTASTIC! She stopped over for a meet and greet prior to coming for the visit to meet them! Played and gave them a snack! Much appreciated! Loved getting the cute pics during the visit!”


“These folks are incredible!! So kind, great with my dog, and very flexible. I’ll be booking again!”



“Anna was excellent in the care of my pups. She was attentive and affectionate towards them. Anna kept me informed about the dogs and took pictures.”


“Deanna was great! I was away longer than usual but felt confident all was well because of Deanna’s detailed updates. Everything was perfect when I came back. I would definitely use her again.”


“Tatum is a gem! She is kind, attentive and very punctual for her visits. Bonus is that our elderly dog loves her! Highly recommend Tatum. Thank you Tatum!”


About: YOᑌ ᕼᗩᗪ ᗰE ᗩT ᗷᗩᖇK 𐂯 I've always had a passion for working with animals, and that love has only grown over the years as I've helped family and friends with their furry friends. I was lucky enough to spend three and a half wonderful years at 4 Dogs Pet Supplies, a charming local shop in Charlotte, NC. It was such a joy to meet so many wonderful dog breeds and discover the best products and care practices for our beloved pets. I also got to team up with another small business, where I had the pleasure of caring for both dogs and cats and plants—everything from playful puppies to treasured older pets. Each day was filled with rewarding experiences in animal care! On top of that, I've volunteered at animal shelters and even participated in an amazing equine therapeutic riding program. These experiences have really deepened my commitment to animal well-being and the importance of supporting our community. It's been a truly fulfilling journey! And am very thankful for those who have trusted me with the animals. ✮ I am currently out of school for the summer and have a part-time job, which gives me plenty of availability to help care for your animals. On Mondays, Wednesdays, and Fridays, I am available anytime after 1 PM for walks, drop-ins, or anything else you need. On Tuesdays, Thursdays, and Saturdays, I can assist at any time. Let me know how I can help! 𐂯 I always strive to treat animals, plants, and homes with the same love and care I give to my own! My goal is to provide the best care possible for my clients, so I ask plenty of questions to understand their preferences. This helps me create a safe and secure environment while building trust with both the owner and their furry friends.

“Being away from my furbabies is always stressful. Nicole was able to ease my stress with her excellent care of my 3 furbabies. One super senior on lots of meds and the other two prior feral makes them not the easiest to care for. Nicole did great with walking, feeding and any special needs that occurred. I will use Nicole again should I need to travel without my furbabies.”

Loving pet sitters in your neighborhood
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Kyla B.Star Sitter

“Kyla did a great job looking after my cats. It was easy to set things up, she arrived as scheduled, communicated well throughout, and my cats liked her too.”


Jeffrey H.Star Sitter

“This was our first time using Rover and we are so glad we found Jeffrey. He took such great care of our diabetic cat so we could rest easy on vacation.”


Catherine C.Star Sitter

“Catherine was great!! She updated and sent pictures every time she stopped in. My one dog Va. be anxious around new people and she instantly made her feel comfortable. I was never worried the entire time I was away.”


Maria & Luis V.
Star Sitter


“Maria and Luis are fantastic pet sitters. Even our very shy cat warmed up to them. We came home to happy cats who got care, play and love while we were away. We will certainly book with them again. Thank you Maria & Luis!”


Tyler H.
Star Sitter


“I’m never using anyone else! Tyler has a genuine love and passion for animals that shows in her visits and when she hosts. You won’t just get pictures of your dog playing in backyard - she actually spends time with your pup”


Allyson B.Star Sitter

“Allyson is the best! I never worry about our dog when she is here!”


Talia C.
About: I’ve taken care of multiple breeds and of varying ages. I’ve also helped train my own puppy, as well as friends’ dogs, the basics like potty training, sit, etc. I’m quite comfortable with puppies under 1 year old all the way to our senior friends. I’m currently a full-time dog mom and pet caretaker. I just graduated from grad school and don’t start my new job until this fall, and I thought - what a better way to spend my summer off taking care of my favorite animal and helping other pet owners? I’m an open communicator and can be available how you need me with the proper heads-up! I live in an apartment building with my fiancé and our sweet, cuddly boy dog (neutered). There’s 3 parks within walking distance and a dog park just an 8min drive away. Since I live in an apartment, I would recommend only small to medium dogs stay with us, but I’m always willing to travel to clients’ houses for dogs of all sizes. I treat my clients dogs as if they were my own fur baby. The love, kindness, & attention I give my sweet boy is the same love, kindness, & attention your dog will receive. My friend is also a vet tech I can always reach out to for advice/questions and I myself am a certified (human) healthcare professional.


Elle P.Star Sitter

“Elle was great with Sake her first time! He went right to her during her care for him. She always left good information on my cards. I will definitely be asking her to help out again. Thank you so much Elle for taking care of Sake. We really appreciate it!!! ??”


Andrew C.Star Sitter

“Andrew has been by far the best dog walker you could ask for. Always going above and beyond. He literally offered to install the portable AC in my house while I was at work and the AC went out. Leaving Richmond is going to be hard but finding anyone better with my dog will be impossible!”


Abby L.Star Sitter

“Abby is awesome! She took great care of our “senior” orange tabby 😽 We got great updates and photos every visit and felt great knowing our boy was in such good hands. Thank you such Abby!”


Alexander S.Star Sitter

“Alexander was awesome! My silly, hyper pup warmed up to him well and he made sure my big oy was taken care of without any deviations from our routine. I will be planning on booking Alexander soon!”


Kay C.Star Sitter

“Kay took excellent care of my 2 cats and my outdoor tomato plants while I was away for a long weekend. Cats were chill and happy upon my return. Kay communicated with me frequently and quickly. I didn't feel like I had to worry about anything while I was away.”


Claire P.

“Claire was FANTASTIC! She stopped over for a meet and greet prior to coming for the visit to meet them! Played and gave them a snack! Much appreciated! Loved getting the cute pics during the visit!”


Ross & Ava T.Star Sitter

“These folks are incredible!! So kind, great with my dog, and very flexible. I’ll be booking again!”




Anna F.

“Anna was excellent in the care of my pups. She was attentive and affectionate towards them. Anna kept me informed about the dogs and took pictures.”


Deanna S.

“Deanna was great! I was away longer than usual but felt confident all was well because of Deanna’s detailed updates. Everything was perfect when I came back. I would definitely use her again.”


tatum f.

“Tatum is a gem! She is kind, attentive and very punctual for her visits. Bonus is that our elderly dog loves her! Highly recommend Tatum. Thank you Tatum!”


Alyssia J.
“Alyssia is an animal lover! She has always cared and loved any animal that has ever crossed her path. When she is around animals you can see and feel the real love and passion she has for them. That is what would make her an amazing sitter. She cares for every animal like they’re her own.”


Nicole P.

“Being away from my furbabies is always stressful. Nicole was able to ease my stress with her excellent care of my 3 furbabies. One super senior on lots of meds and the other two prior feral makes them not the easiest to care for. Nicole did great with walking, feeding and any special needs that occurred. I will use Nicole again should I need to travel without my furbabies.”


ashley g.

“Ashley was amazing!! She sent lots of cute pics of the kitties and sent a nice note of everything she did while she was there!! Will definitely book with her next time!”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
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Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Windsor.
Rover makes it easy to find Windsor pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
