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

“Kade is awesome! Our dog is a handful, but Kade matches him stride for stride. The house is always just as well left it, if not better, and they are always going above and beyond. Highly recommend!”


“Thane was great with Rat! They took the time to understand his personality and routine during our meet and greet which put me at ease. I’d definitely hire them again :)”


“Absolutely wonderful with my girl! My timid pup warmed right up to her, which usually does NOT happen so quickly, and loved the company. Kyla was responsive, communicative and was really great working with. Will definitely book with her again!”


“Cat is an amazing sitter! She takes great care of my puppy and is very accommodating with her times. She is reliable and best buds with my little puppy girl. A must book if you’re looking for somebody to treat your dog like you would!”


“Kathleen was able to come check on my pup without tons of notice and she was absolutely incredible. So communicative, loved on the pup and took the cutest photos of him. Would totally recommend her and will absolutely use Kathleen again !”


“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”


“I’m so glad I chose to book with Devinder! I’ve been blown away by his responsiveness, flexibility, communication, and clear love for pets :) He’s very professional, but also comes across like a friend who’s always down to help you out and care for your pets like they’re his own. I trust him with my pets for the long haul!”


“Maria & Luis did a fantastic job taking care of Brutus. They were timely with their drop-ins, they kept us up to date with how he was doing, and provided plenty of photos. I would highly recommend them to anyone looking for someone to help take care of your pets!”


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.

“Cynthia was a great pup-sitter, and kept me well informed with pictures and updates! Sebastian tends to be anxious and he looked like he didn’t miss a beat of belly rubs, cuddles, walks and attention. She communicated all needs and changes in behavior during my time away! She was a great sitter!”


“Abby was quick to respond to our request and was communicative through the whole process! She went above and beyond to take a package inside for us, ask about the litter box, and even played with the kitties and gave them some treats!”


“Elle took amazing care of my dogs with drop in visits for over 6 months and they both love her so much! She always took the best pictures and sent me updates. I would highly recommend Elle to anyone looking for a great dog sitter!”


“Rachel took great care of my dogs when I was away. She was very communicative and kept me well updated about how the dogs were doing the entire time. I would definitely book Rachel again!”


“Katherine took great care of our pups. She was on time, responsive, and followed all of our instructions. She did such a great job that we already booked her for another weekend. Would definitely recommend!”


“Hollie was wonderful with our two pups! One is a little more shy, but she still won her over and approached her with so much care. Hollie is highly communicative, responsible, and provided great care. Thank you, Hollie :)”


“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!”


“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!”


About: there! I’m Jordyn Reid, your friendly neighborhood pet sitter. 🐾 I'm a full-time professional by day at VCU, but when I'm not working, I’m all about spending time with animals! Whether it’s a quick walk, playtime in the yard, or some quality cuddle time, I’ll make sure your pet feels loved and cared for. I’ve always had a deep connection with animals—growing up with dogs, cats, and even the occasional guinea pig. .I have worked in pet care for a good majority of my life,in grooming ,kennels, and shadowing veterinarians.I know how important it is for pets to feel comfortable and secure, especially when their humans are away. So, while I'm working my 9-to-5, I’m still here to offer drop-in visits, evening walks, and weekend care to give your furry friend the attention they deserve. I understand the need for flexibility and will work with your schedule to make sure your pet is in the best hands, whether it’s a long walk, an afternoon snack, or some evening snuggles. 🐶 I currently work full-time but would love to take care of your furry ones around my regular 9-5 job . I am always very available on weekends. I would prefer to sit at your home ,as I find animals more comfortable in surroundings they can recognize ,and my roommate does have a dog who does not get along with other pets so for their safety , I would board at their home. Also when i go on walks I do make sure to keep all other animals away ,as I have learned that some pets just do not get along. I don't feed pets human food ,unless you as the owner is comfortable with that .And I love taking pics of pets so you will constantly be reassured that your little one is happy and safe.
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.


Kade M.
Star Sitter


“Kade is awesome! Our dog is a handful, but Kade matches him stride for stride. The house is always just as well left it, if not better, and they are always going above and beyond. Highly recommend!”


Eula C.
Star Sitter


“Thane was great with Rat! They took the time to understand his personality and routine during our meet and greet which put me at ease. I’d definitely hire them again :)”


Kyla B.Star Sitter

“Absolutely wonderful with my girl! My timid pup warmed right up to her, which usually does NOT happen so quickly, and loved the company. Kyla was responsive, communicative and was really great working with. Will definitely book with her again!”


Meghan F.

“Meghan was very sweet and thorough. I appreciate her taking notes during our meet and greet and greet very detailed reports when she checked in on the dogs!”


Catherine C.Star Sitter

“Cat is an amazing sitter! She takes great care of my puppy and is very accommodating with her times. She is reliable and best buds with my little puppy girl. A must book if you’re looking for somebody to treat your dog like you would!”


Kathleen L.Star Sitter

“Kathleen was able to come check on my pup without tons of notice and she was absolutely incredible. So communicative, loved on the pup and took the cutest photos of him. Would totally recommend her and will absolutely use Kathleen again !”


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”


Devinder K.Star Sitter

“I’m so glad I chose to book with Devinder! I’ve been blown away by his responsiveness, flexibility, communication, and clear love for pets :) He’s very professional, but also comes across like a friend who’s always down to help you out and care for your pets like they’re his own. I trust him with my pets for the long haul!”


Maria & Luis V.
Star Sitter


“Maria & Luis did a fantastic job taking care of Brutus. They were timely with their drop-ins, they kept us up to date with how he was doing, and provided plenty of photos. I would highly recommend them to anyone looking for someone to help take care of your pets!”


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.”


Cynthia B.Star Sitter

“Cynthia was a great pup-sitter, and kept me well informed with pictures and updates! Sebastian tends to be anxious and he looked like he didn’t miss a beat of belly rubs, cuddles, walks and attention. She communicated all needs and changes in behavior during my time away! She was a great sitter!”


Abby L.Star Sitter

“Abby was quick to respond to our request and was communicative through the whole process! She went above and beyond to take a package inside for us, ask about the litter box, and even played with the kitties and gave them some treats!”


Elle P.Star Sitter

“Elle took amazing care of my dogs with drop in visits for over 6 months and they both love her so much! She always took the best pictures and sent me updates. I would highly recommend Elle to anyone looking for a great dog sitter!”


Rachel R.

“Rachel took great care of my dogs when I was away. She was very communicative and kept me well updated about how the dogs were doing the entire time. I would definitely book Rachel again!”


Katherine I.

“Katherine took great care of our pups. She was on time, responsive, and followed all of our instructions. She did such a great job that we already booked her for another weekend. Would definitely recommend!”


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!”


Shaine S.Star Sitter

“Hollie was wonderful with our two pups! One is a little more shy, but she still won her over and approached her with so much care. Hollie is highly communicative, responsible, and provided great care. Thank you, Hollie :)”


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!”


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!”


Jordyn R.
“Jordyn pet sat for me at the last minute , and she was exceptional in not only response ,but in care .I have two elderly dogs and a young husky , so I know it was a lot to handle , but she did with grace . She stayed over the weekend ,and when I got back I swear they were sadder to see me ,knowing that she had to go .I will be a recurring client of hers !!!”
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?
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 Oakwood.
Rover makes it easy to find Oakwood 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.
