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.
Confirmed availability
Christmas and New Year
1. Kadeja

I’ll treat your dog as my own. love

Hickory Hill, Richmond, VA, 23234

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

"Kadeja is a happy, energetic person. She has a great spirit and is an outgoing person. Her best friend is Lexii, her fur pal. She demonstrates so much love ... (more)"

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2. Bree

Your pet's new BFF

Church Hill, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"The Best! I have a very old dog and I felt like I left him with a family member. Updates were great and my dog was well loved while I was away. Stayed at my ... (more)"

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3. Jess

Available for last minute requests!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Jess was great! She watched our 10 week old puppy and 6 year old dog on a short notice basis for 2 nights. She sent us pictures and videos throughout the wee... (more)"

4. Paige

I'll treat them like my own!

Vcu, Richmond, VA, 23220

House Sitting, Drop-In Visits, Dog Walking

"Paige P. comes with strong recommendation and experience. Being a avid lifelong dog lover, raising her dog Flare (9 yrs old) from 4wks old to present she has... (more)"

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5. Ifeatu

Sick of high costs- hire me :)

Union Hill, Richmond, VA, 23223

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

"10/10 would recommend not only for being in the care of my 2 pit bulls but sensing the stress in my messages when another sitter canceled on us last minute a... (more)"

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6. 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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7. 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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8. Annie

Life-Long Dog Pal - Let's Walk!

Jackson Ward, Richmond, VA, 23220

House Sitting, Drop-In Visits, Dog Walking

"Annie was fantastic! She sent lots of pictures and our house was neat and tidy when we got back. Our critters were definitely in the best of hands! (more)"

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9. Lindsey

Have leash, Will travel!

Jackson Ward, Richmond, VA, 23219

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

"Lindsey house sat our two golden girls for a long weekend and we could tell they were loved, cared for, and played with! She was so sweet to send consistent ... (more)"

10. Shelby

Animal lover ready to help you!

Old Town Manchester, Richmond, VA, 23224

House Sitting, Drop-In Visits, Dog Walking

"Shelby was fantastic!! She was so friendly, warm , and responsible! Our hearts were at ease knowing we had someone so loving to be with our sweet guy. We co... (more)"

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11. Julie

Grew up with 4 legged family

Oregon Hill, Richmond, VA, 23220

House Sitting, Drop-In Visits, Dog Walking

"Trouble really enjoyed her time with Julie!!! I had a very happy content dog after her stay. Julie sent me pictures and updates daily which were great! I ... (more)"

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12. Nick

Will take great care of your pets

Richmond, VA, 23224

House Sitting, Drop-In Visits, Dog Walking

"Nick’s helped us over 20 years with our dogs and cats like they were his own. A caring animal lover with a calm and peaceful energy. Our pets adore him. (more)"

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13. Carla

Looking for an exercise buddy!

Central Office, Richmond, VA, 23219

House Sitting, Drop-In Visits, Dog Walking

"Carla is wonderful! She showed my pet the love and attention he needed throughout his stay. Frequent walks and feeding schedules were documented with picture... (more)"

14. Jonathan

Motivated, caring, animal sitter

Union Hill, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"I have used Jonathan three times now and he continues to take wonderful care of my dog. His communication is excellent and I feel extremely comfortable with ... (more)"

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15. Martin

Part-time home large fenced yard

Richmond, VA, 23224

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

"Martin is an extraordinary pet caregiver!!! I have asked him to look after my dog on multiple occasions and he has done beyond a superb job of caring for my ... (more)"

16. Henry

I will be your dog's best friend

Fulton, Richmond, VA, 23231

House Sitting, Drop-In Visits, Dog Walking

"Henry really loves dogs. He gets really excited to be around them when he sees one. Can't get wait to get near dogs to pet them and hug them. He has owned... (more)"

Confirmed availability
Christmas and New Year
17. Crystal

On-Call Doggo Lover

Richmond, VA, 23224

House Sitting, Drop-In Visits, Dog Walking

"My friend, Crystal, is amazing with dogs. She’s kind, upbeat, and super sweet! I can always rely on her to help out with my dog and my dog is always excited ... (more)"

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18. Joseph

Every Dog Deserves Love

Shockoe Bottom, Richmond, VA, 23223

House Sitting

"We have just moved from out of state and have been so happy to find Joey to sit for our 2 dogs. Joey stayed overnight with them, he is very dependable and ea... (more)"

Confirmed availability
This weekend
19. Allyson

I’ll treat your pet like my own.

Henrico, VA, 23231

House Sitting, Drop-In Visits, Dog Walking

"Allyson is a dog and cat lover and would provide excellent care for your pet. She was a dog sitter for our Beagle and she did an excellent job. She is would ... (more)"

Confirmed availability
Christmas and New Year
20. Andrea

Twelve year experience in pet care

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Ben and George couldn't have had a better dogsitter! She kept us up to date when she was here. Alerted us to George's anxiety, and even took the time to b... (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.