House Sitting in Oakland, VA

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Annie

Life-Long Dog Pal - Let's Walk!

Jackson Ward, Richmond, VA, 23220

House Sitting, Drop-In Visits, Dog Walking

"Annie was absolutely fantastic with my pup. Reina is weary of new people so I was a bit nervous to leave her for the weekend but Annie was sure to update me ... (more)"

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2. Bree

Your pet's new BFF

Church Hill, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"We liked Bree from the moment we met her! She was so friendly and purposeful with the questions she asked. It was nice to know that our boys were in such goo... (more)"

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3. Chandler

Young, energetic, ready to go

Richmond, VA, 23224

House Sitting, Drop-In Visits, Dog Walking

"Really liked meeting Chandler and then having him stay at our house with our pets. He was easy to communicate with, flexible, and I trusted his experience. O... (more)"

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4. Michelle

Engineer, Runner, Dog Lover!

Central Office, Richmond, VA, 23219

House Sitting, Drop-In Visits, Dog Walking

"It’s a very scary thing to leave your house and fur babies with someone you don’t know. That being said as soon as I met Michelle she immediately put me at e... (more)"

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5. Schyller

Active, Trustworthy, and Flexible!!

Northrop, Richmond, VA, 23225

House Sitting, Drop-In Visits, Dog Walking

About: Growing up with a pet friendly family I was able to learn at an early age that all lives are to be respected and loved unconditionally. From puppie... (more)

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6. Bekka

Dog Lover

Carver, Richmond, VA, 23220

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Bekka did a great job taking care of my girls. She left the house tidy and the dog tuckered out from playing. I would definitely request her services again. (more)"

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7. Jess

Looking for new furry friends!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Jessica is an awesome dog sitter. She has cared for my sweet pup on multiple occasions. She walks, plays and cuddles my pup. I highly recommend her to sit fo... (more)"

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8. Allison

Love to see each dog's personality!

Monroe Ward, Richmond, VA, 23220

House Sitting, Drop-In Visits, Dog Walking

"Allison babysat my one year old grandson for 2-3 hours a day, 4-5 days a week, through the summer. She was always on time and was also very flexible on days... (more)"

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9. Sheila

Compassionate care for your canine!

Upper Shockoe Valley, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"This was my first time utilizing Rover and i will have a hard time not requesting Sheila in the future. Sheila stayed in our home while we were gone for the ... (more)"

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10. Maddie

Help me explore RVA!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I'm a New York via DC transplant to Richmond, and I'd love to get out of the house more and have a dog join me! I grew up in a house with ca... (more)

Confirmed availability
This weekend
11. Anna

Friendly dog walked next door!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

About: I have had the wonderful experience of growing up with dogs! They were always my best friends when I was young. Since then I have spent the last 4 ... (more)

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12. Ifeatu

Sick of high costs- hire me :)

Union Hill, Richmond, VA, 23223

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I love dogs. Ever since I was able to have one I’ve always had a dog and it will always be that way. I’m not here to break the bank in dog sitting.... (more)

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13. Shelby

Animal lover ready to help you!

Old Town Manchester, Richmond, VA, 23224

House Sitting, Drop-In Visits, Dog Walking

"Shelby was amazing! She was so caring and remembered everything important I told her about during the meet and greet. She sent me photos all day and kept me ... (more)"

Confirmed availability
This weekend
14. Kelsey

Let me love your pup like my own!!

Upper Shockoe Valley, Richmond, VA, 23223

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I just moved to Richmond maybe three weeks when I landed in the hospital needing surgery. I contacted Kelsey and told her my situation. I was more worried th... (more)"

15. Jonathan

Motivated, caring, animal sitter

Union Hill, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"I am so appreciative of Jonathan. He took good care of my old dog with her quirks. He's very pleasant to work with and sent daily updates and was responsive... (more)"

16. Glencora

Excited to meet your best friend!

Chimborazo, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Glencora is a very responsible and compassionate person. She engaging with pets and people. She recognizes and anticipates their needs (and mine). And Glenco... (more)"

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17. Matty

Young, active graduate student!

Union Hill, Richmond, VA, 23223

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Matty watches my dog, Molly, every time I’ve out of town and he’s awesome! He is responsible with Molly and sends me updates and pictures throughout the stay... (more)"

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18. Danica

Active Walker, Boarder & Sitter!

Church Hill, Richmond, VA, 23223

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Danica is friendly, trustworthy and reliable! She loves dogs and doggie kisses. I highly recommend her for all of your pet needs. She is great. (more)"

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19. Morgan

I yell "DOG" everytime I see one.

Chimborazo, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"I've been using Morgan to dog sit for me for almost a year now. She's great! I get lots of pictures of my dog and she's always taking him somewhere new aroun... (more)"

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20. Lisa

Home full-time and ready to play!

Fulton, Richmond, VA, 23231

House Sitting, Drop-In Visits, Dog Walking

About: What you'll love about me most is my flexible schedule. I'm available everyday to help take care of your pup! If you got an active dog, I'll run wi... (more)


Rover.com is the simple, savvy way to find and book Oakland house sitting. It's easy to find the perfect house sitter — many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Oakland on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Oakland house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.