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.
“Rachel is the best cat sitter! She is so communicative and is able and happy to deal with my quirky cats! They can be timid with new people but they have liked Rachel from the start. I will always use and recommend Rachel!”
“This was our first time having Jeffrey do drop ins for our three wild kids and he was AMAZING! Great communication, super professional, loved on our doggos just like we would!”
“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 services through Rover and we are so glad we did! Cat was absolutely amazing through the entire process keeping us well informed at each drop in. She was incredibly patient with our fur babies and their unique personalities, even befriending our shy boy in record time. Thank you so much, Cat!”
“Thank you Maria and Luis for watching Neyland and Nala while I was out of town! I booked them a few days prior because my dog contracted kennel cough from daycare. Maria did a meet and greet with me, took Neyland outside 3 times a day, and gave him his food with medications. Neyland is reactive with people and dogs but they handled him wonderfully! Thank you guys :)”
“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”
“Kathleen was amazing with our dogs ! She was super sweet, reliable, caring , flexible and a great communicator. Would definitely book with her again!”
About: I'm officially back and excited to work with new clients! What really sets me apart is my genuine love for animals of all shapes, sizes, and personalities. Through my volunteer work with rescue organizations, humane societies, and wildlife rehabilitation centers, I've learned to connect with pets who might be shy, anxious, or just need a little extra patience. I'm especially comfortable with senior pet care (thanks to my own elderly cats), medication administration, and working with special needs animals. My late staffie rescue taught me that the most misunderstood dogs often make the most loyal companions, so I have a real soft spot for bully breeds and "difficult" cases. I've also got experience with puppy energy management – I can tire out even the most determined zoomie sessions! Friends joke that I'm a "cat whisperer," though I'll admit one particularly stubborn feline took me 15 years to win over. Whether your pet needs gentle senior care, high-energy adventures, or just someone who won't blink at their quirky habits, I'm here for it. No creature is too unusual – I've cared for everything from traditional pets to more exotic companions! After leaving academia to pursue my passion for writing and art, I've discovered the joy of a flexible schedule. I spend most of my time outdoors anyway (turns out fresh air is much better for creativity than stuffy lecture halls), so having some four-legged companions along for the adventure sounds like a no-brainer. Plus, I've learned that pet adventures are the perfect antidote to writer's block. I believe every pet deserves to feel safe and loved while you're away. I'm experienced with administering medications, maintaining routines, and reading those subtle pet signals that tell you when something's not quite right. My own little crew includes two senior cats (14 and 17) and a wonderfully patient yellow lab who's basically a gentleman and a scholar. One of my cats has special needs, so I'm comfortable with medical care and know how important consistency is for our furry family members.
“Riley was an awesome find. We are new to the Williamsburg area but have used Rover in the past and had a trusted pet sitter that we loved and now looks like we have found one here in Williamsburg. Riley sent great recaps and super pictures after each of her visits. You could tell all of our pets (even our cat that does not like strangers) were very happy to see her and hang out at each of her visits. She communicated well with any changes or concerns and just put our minds at ease that our pets were well taken care of while we were away. I would highly recommend Riley for cat, dog or both care”
“First time having Nick care for our fur babies! Nick is a great young man who clearly loves animals. He was punctual for our meet and greet as well as drop in visit to care for our pups! Would highly recommend and will definitely be calling on him for future needs!”
“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!”
“Julia is the absolute best. Booked on short notice and my two year old lab had an amazing time with her. Provided timely updates and photos throughout the day. Will definitely be booking again!”
“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!”
“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.”
About: Hey there! I’m Jess! I’m 31 years old and I absolutely adore animals. I have 20 years of experience in caring for a wide variety of animals. I’ve been house/pet sitting since I was 10 years old. I have experience in caring for all animals with a specialty in exotics. I’m very flexible on when and where you need me as well as pay. Contact me so we can chat about your options! I have over 10 pets of my own (of wide variety) that get fed and played with daily. There is no job too small or too big for me. I am one for routine when necessary, so I will make sure your pet doesn’t get too stressed over their parents being away. I also have pets of my own to bring on walks or play dates if your pet is social.
Loving pet sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Rachel H.
“Rachel is the best cat sitter! She is so communicative and is able and happy to deal with my quirky cats! They can be timid with new people but they have liked Rachel from the start. I will always use and recommend Rachel!”
Jeffrey H.Star Sitter
“This was our first time having Jeffrey do drop ins for our three wild kids and he was AMAZING! Great communication, super professional, loved on our doggos just like we would!”
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.”
Catherine C.Star Sitter
“This was our first time using services through Rover and we are so glad we did! Cat was absolutely amazing through the entire process keeping us well informed at each drop in. She was incredibly patient with our fur babies and their unique personalities, even befriending our shy boy in record time. Thank you so much, Cat!”
Maria & Luis V.
Star Sitter
“Thank you Maria and Luis for watching Neyland and Nala while I was out of town! I booked them a few days prior because my dog contracted kennel cough from daycare. Maria did a meet and greet with me, took Neyland outside 3 times a day, and gave him his food with medications. Neyland is reactive with people and dogs but they handled him wonderfully! Thank you guys :)”
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”
Kathleen L.Star Sitter
“Kathleen was amazing with our dogs ! She was super sweet, reliable, caring , flexible and a great communicator. Would definitely book with 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!”
Christine V.
“Christine has watched my 6 year old Corgi over several weekends, and I have always felt he was in good hands. She takes him on frequent walks and often sends photos to reassure me how he is doing. I highly recommend her for reliable and friendly pet care.”
Abby L.Star Sitter
“Abby took great care of our two crazy cats, even though our request was on short notice!! Would definitely recommend her to watch your little ones 😊”
Riley B.Star Sitter
“Riley was an awesome find. We are new to the Williamsburg area but have used Rover in the past and had a trusted pet sitter that we loved and now looks like we have found one here in Williamsburg. Riley sent great recaps and super pictures after each of her visits. You could tell all of our pets (even our cat that does not like strangers) were very happy to see her and hang out at each of her visits. She communicated well with any changes or concerns and just put our minds at ease that our pets were well taken care of while we were away. I would highly recommend Riley for cat, dog or both care”
Allyson B.Star Sitter
“Allyson was great and helped out with my two crazy girls on short notice!”
Danyelle H.
“Danyelle was awesome, she had great communication skills and took lots of pictures and care of my cats during her drop in visits. Highly recommend!”
Nick I.Star Sitter
“First time having Nick care for our fur babies! Nick is a great young man who clearly loves animals. He was punctual for our meet and greet as well as drop in visit to care for our pups! Would highly recommend and will definitely be calling on him for future needs!”
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!”
Julia M.
“Julia is the absolute best. Booked on short notice and my two year old lab had an amazing time with her. Provided timely updates and photos throughout the day. Will definitely be booking again!”
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!”
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.”
Ross & Ava T.Star Sitter
“These folks are incredible!! So kind, great with my dog, and very flexible. I’ll be booking again!”
Jessica Z.
“Jessica is one of the more caring and compassionate pet caregiver I know! I have known her for most of my life and she has taken care of our two dogs and kitty multiple times! They always miss her when she leaves! She would be PURRRRFECT to take care of anyone’s pets!!! 1000/10!”
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 pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
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!
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 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.
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