Pet Sitting & Drop Ins In Oakwood

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 15% and taxes will apply.

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Sitter Profile Image: Emily H.
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Emily H.
Star Sitter
from
$21
per visit
5.0 out of 5 stars
131 reviews
56 repeat clients
6 years of experience
Chimborazo, Richmond, VA, 23223

Emily was great! She communicated so well and was super attentive to my boys! I would definitely use her services again. Highly recommend her!!

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Tori T.
Sitter Profile Image: Alyssa M.
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Alyssa M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
33 reviews
11 repeat clients
15 years of experience
Chimborazo, Richmond, VA, 23223

Alyssa has been an amazing pet sitter for our high-energy dog. She has been great with our unpredictable schedule and has been an awesome communicator. We are very grateful we could find her on Rover!

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Mary C.
Sitter Profile Image: Nick I.
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Nick I.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
36 reviews
12 repeat clients
10 years of experience
Fulton, Richmond, VA, 23231

Nick’s care and communication have been absolutely phenomenal, and I truly appreciated it. I could tell Sebastian felt well loved and cared for through the pictures that he sent during my time away! This was my first time using Rover, and I'm sold. I'll definitely keep Nick in mind as I travel frequently, and we've had some family shifts so care is not always as readily available.

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Ashley W.
Sitter Profile Image: Abby L.
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Abby L.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
234 reviews
79 repeat clients
8 years of experience
Richmond, VA, 23223

Abby was so wonderful and considerate while watching our cat. She went above and beyond to make sure her needs were met while also taking care of the house. We are glad to have found her.

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Windsor B.
Sitter Profile Image: Erica P.
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Erica P.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
42 reviews
14 repeat clients
30 years of experience
Central Office, Richmond, VA, 23219

Erica was a huge help to us watching our dog and looking after our garden!! From all the photos my dog looked so happy and comfortable. Would definitely book again!

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Anna M.
Sitter Profile Image: Danyelle H.
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Danyelle H.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
69 reviews
19 repeat clients
20 years of experience
Shockoe Bottom, Richmond, VA, 23223

Danielle did an excellent job with Otis, kept me updated with pics and videos from her visits. He's not always the quickest to warm up but seemed to take to her on her first visit! Came home to a happy, healthy boy. Would definitely book her to look after him again!

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Andrew T.
Sitter Profile Image: Heather S.
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Heather S.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
25 years of experience
Fulton, Richmond, VA, 23231

Heather was very responsive and communicative. She took great care of our cat, followed all our instructions and is the first pet-sitter he came out for. She was very respectful of our house. We would definitely rebook with Heather again!

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Alex G.
Sitter Profile Image: Elijah S.
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Elijah S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
249 reviews
74 repeat clients
4 years of experience
Eastview, Richmond, VA, 23223

Elijah has a special way with our boys, even the shy one comes out for each visit. Appreciate the great communication and play time with the boys. 5 stars!

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Amber B.
Sitter Profile Image: Maria & Luis V.
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Maria & Luis V.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
209 reviews
76 repeat clients
25 years of experience
Church Hill, Richmond, VA, 23223

Wonderful service , was friendly and made me feel very comfortable leaving my fur baby in her care. She kept me updated and took great care of my kitty and even brought in the mail - will definitely repeat when I leave town again

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F B.
Sitter Profile Image: Chynna N.
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Chynna N.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
17 reviews
7 repeat clients
14 years of experience
North Highland Park, Richmond, VA, 23222

Chynna was so wonderful with our senior Bostons I felt like she looked after them like they were her own. I really appreciated all the photo updates and the extra attention she gave them while we were away! We will definitely have her watch our pups again 💯🧡

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Devon M.
Sitter Profile Image: Sidney D.
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Sidney D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
58 reviews
18 repeat clients
20 years of experience
The Fan, Richmond, VA, 23220

Sidney is great with our puppy and was very accommodating to do a drop-in on short notice. Would recommend her to anyone looking for drop-ins and dog walks!

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Kyle D.
Sitter Profile Image: Holland H.
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Holland H.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
66 reviews
16 repeat clients
8 years of experience
Richmond, VA, 23220

Holland was great! My cat seemed happy us usual when I got back from my trip, and Holland was great about sending me pictures and videos. She came when she said she would and she sent me videos of how she played with him to assure he was getting his energy out! I would definitely recommend her to anyone and will definitely look to use her again!

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Madelyn F.
Sitter Profile Image: Ivana M.
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Ivana M.
from
$20
per visit
5.0 out of 5 stars
31 reviews
13 repeat clients
10 years of experience
Shockoe Bottom, Richmond, VA, 23223

About: I offer daycare, overnight stays, walks and check ins! I’ll make sure your pet gets the love and attention they deserve. Frequent trips to the dog park and lots of long walks. As a long time pet owner I know how important it is to care for your pet properly and be able to trust they are in good hands. I have experience caring for old dogs as well as sick dogs that require lots of attention and medication. I am experienced in caring for puppies. Will provide hourly check ins when requested including photos. Dogs allowed on furniture. Will never leave them alone. Available on short notice. Hourly Over 10 years experience. Rest assured your pet will be in very good hands staying with me.

Sitter Profile Image: Fran M.
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Fran M.
from
$22
per visit
5.0 out of 5 stars
18 reviews
4 repeat clients
12 years of experience
Shockoe Bottom, Richmond, VA, 23223

Fran did an excellent job sitting my 2 cats. She sent me pictures and even cute videos of them. That eased my mind while I was away. I felt very secure leaving them with her. She asked great questions before I left and kept in great communication with me as I was gone. I will definitely ask her to cat sit again.

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Becca S.
Sitter Profile Image: Cynthia B.
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Cynthia B.
from
$22
per visit
5.0 out of 5 stars
39 reviews
23 repeat clients
3 years of experience
Woodville, Richmond, VA, 23223

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!

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Ashley W.
Sitter Profile Image: Elle P.
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Elle P.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
45 reviews
11 repeat clients
10 years of experience
Richmond, VA, 23223

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!

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Matt H.
Sitter Profile Image: Maggie D.
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Maggie D.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
23 reviews
4 repeat clients
20 years of experience
Monroe Ward, Richmond, VA, 23220

Maggie is so kind and wonderful with my two cats. She’s so thoughtful and detail oriented and I really appreciated her help while we were away. Maggie is a great rover!

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Valerie M.
Sitter Profile Image: Kacey G.
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Kacey G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
44 reviews
13 repeat clients
12 years of experience
Upper Shockoe Valley, Richmond, VA, 23223

Kacey was so great with Rosie! She made sure she had everything she needed and took lots of photos for us. Definitely recommend her for all your pets!

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Seana C.
Sitter Profile Image: Rachel D.
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Rachel D.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
175 reviews
76 repeat clients
18 years of experience
Richmond, VA, 23223

Rachel was great! She was flexible and responsive when I need to make some last minute changes and my boys seems to love her! She is definitely a jewel!

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Lydia W.
Sitter Profile Image: Paris W.
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Paris W.
from
$17
per visit
10 years of experience
Church Hill North, Richmond, VA, 23223

About: Graduate Student at VCU with flexible summer hours ready to care for your animals. I’ve been a lifelong pet owner with hands-on experience caring for both dogs and cats. I also have previous experience dog sitting and walking specifically dogs. I’ve trained my own cockapoo (who was definitely my soul dog), including basic commands and good behavior habits, and currently manage all care for a senior beagle/lab mix, including her vet visits, medications, and daily routines. I’m also experienced with cat care through shared custody of our cat, Judah with my roommate. I’m attentive, patient, and committed to making pets feel safe, comfortable, and well cared for. I maintain a flexible schedule that allows me to offer consistent morning and afternoon availability for pet care. I prioritize reliability and clear communication, and I’m happy to work with families to find a routine that fits their needs. As I build long-term relationships, I’m open to expanding availability to best support both pets and their owners I tailor my approach based on each type of service I provide. During walks, I prioritize leash safety, awareness of surroundings, and your dog’s comfort with pace, weather, and other animals. For drop-in visits, I focus on maintaining your pet’s routine in a familiar environment—proper feeding, clean spaces, and attentive check-ins while respecting their home. For house sitting, I create a calm, consistent environment by following established routines, providing companionship, and keeping your home secure. Across all services, my priorities are clear communication, reliability, and building trust with both pets and their owners.

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Oakwood pet parents share their Rover experiences

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5.0 out of 5 stars

Macee was awesome! She was great with communication and took amazing care of our dogs! Both of our dogs take medication and Macee did phenomenal making sure they took it. I will definitely be booking with her again!

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Taylor B.
Drop-In Visits
5.0 out of 5 stars

Abby was so communicative and sent so many photos of my babies! Would highly recommend her and will definitely be using her again :)

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Alyssa D.
Drop-In Visits
5.0 out of 5 stars

Alyssa is fantastic with communication and taking care of Chico! I love knowing he’s well cared for when I’m gone.

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

Maggie was so amazing! She uploaded photos, messaged updates, and you could tell she really loves animals 💛 Absolutely will be asking for Maggie again!!

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Samantha J.
Drop-In Visits
5.0 out of 5 stars

Heather was great! She was communicative, responsive, and prompt when coordinating care instructions and when reaching out in response. She followed instructions and provided consistent and helpful updates. I loved getting updates and photos throughout the day. It helped give me peace of mind while being away for 12 hours. I absolutely recommend her, and look forward to a repeat booking in the future.

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Elizabeth S.
Drop-In Visits
5.0 out of 5 stars

Kade communicated well the entire stay, sent plenty of pictures and told me everything I wanted to know regarding my kitty. I couldn’t have asked for a better person to work with her.

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

Erica was on time for visits and took great pictures! I felt very comfortable entrusting her with Clover after our meet and greet.

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Katie G.
Drop-In Visits
5.0 out of 5 stars

Danyelle was amazing with our indoor and outdoor cats, she sent a lot of pictures and details about each visit. I would recommend Danyelle to others and will be booking her for pet sitting again!

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

Emily was professional & friendly, and the cats--especially Phoebe--certainly loved her! One of our kitties had a bit of a medical emergency and Emily handled it with grace and care. Could not recommend her enough! :)

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

Nick is the best! He’s great with Chico and always excited to see him. He keeps me updated on the visit and often says yes to my last minute requests. So grateful to have him watching Chico!

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

Elijah took great care of the cats as usual, looking after the basics while being proactive and engaging with play-time and scratches every day!

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Michael J.
Drop-In Visits
5.0 out of 5 stars

Emily was great! Great with my two cats and super sweet and communicative. I will definitely book with her again!

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

Chynna took great care of our two cats. They liked her immediately when she came over to walk through things and they also looked happy in the photos she sent. Thank you, Chynna!

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Allison D.
Drop-In Visits
5.0 out of 5 stars

Per usual, Kelly's the absolute best at handling our cantankerous old man cat. I'd even go as far as saying she's growing on him, which no one has achieved before in his 15 years on this planet. Either way, we love Kelly even if Mowgli doesn't (because he hates everything).

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Jessica V.
Drop-In Visits
5.0 out of 5 stars

Kirby is awesome! She took such good care of my sweet boy Dino! This was my first time using Rover & Kirby put all my nerves at ease. The report card & photos were sweet & helpful. Would definitely recommend Kirby to anyone looking for responsible, loving care for their fur baby 🩷

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Adrianna G.
Drop-In Visits
5.0 out of 5 stars

Goes above and beyond!!! Very trustworthy and kind. I have been hiring Terra for the past couple years and highly recommend them!

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

Jordyn was great! Communicative and able to take on the booking only a few days out. Rocky seemed like he had a great time, would recommend!

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Madison J.
Drop-In Visits
5.0 out of 5 stars

Brenna has communicated well and been reliable. We did a FaceTime meetup before our first sit and have now used her twice and hope to continue to do so.

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

Catherine always gives my furbabies lots of love and attention. I usually feel anxious leaving them behind but I feel better knowing they are in safe and affectionate hands with her.

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

Kayley was able to step on last minute to watch my Nova for the weekend. While I attend a family funeral. Nova had the best time on their play dates & walks. Her updates were throughout, efficient and loving as always!

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Katania C.
Drop-In Visits
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How Rover works

  1. 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. 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. 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!

The median cost per night for pet sitting in Oakwood is NOK 14

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

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Oakwood on Rover as of Jun 2026 was about NOK 14 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

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.