Pet Sitting & Drop In Visits in Stephenson, VA

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

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1. Rebecca

I love all dogs - flexible schedule

Winchester, VA, 22601

House Sitting, Drop-In Visits, Dog Walking

"Becca is a natural with dogs! From the first time my dog met her, he fell in love with her. He is blind and can be nervous, but he was comfortable with her r... (more)"

Confirmed availability
4th of July
2. Emilie

Experienced multiple dog caregiver

Winchester, VA, 22602

House Sitting, Drop-In Visits, Dog Walking

"She was amazing!! I dog got hurt while I was gone and she handled it so well, I am so thankful for her help with my fur baby. (more)"

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3. Heather

Ready to be Your Dog's Best Friend

Winchester, VA, 22602

House Sitting, Drop-In Visits, Dog Walking

"Heather took care of ours cats while we were on a short trip. She made sure the cats were well fed and even went out of her way to sweep the floor. She was v... (more)"

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4. Lizz & Bradley

I'll play with your dog!

Winchester, VA, 22601

Drop-In Visits, Dog Walking

"Lizz is awesome! She's great with my dog and I love knowing he's getting excersise while we're working. He's a high energy pup so the extra playtime and walk... (more)"

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5. Ashley

Part-time student - flex schedule

Winchester, VA, 22601

Drop-In Visits, Dog Walking

"Ashley was great at taking care of my pets while I was away on vacation. She is very reliable and communicates promptly about any issues. She has built an ex... (more)"

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6. Brianna

Flexible, active and dog-educated!

Winchester, VA, 22601

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

"Brianna will make an excellent dog sitter. Animals are her passion, she's so good with dog especially. Anytime there is a problem with my dog i go to her and... (more)"

Confirmed availability
4th of July
7. Kristen

Sit, Stay & Play!

Winchester, VA, 22601

House Sitting, Drop-In Visits, Dog Walking

"Kristen is Great! I would recommend her to anyone! Thanks so much! :) (more)"

Confirmed availability
4th of July
8. Karis

Family of dog lovers!

Winchester, VA, 22601

House Sitting, Drop-In Visits, Dog Walking

"Karis babysat my two kitty cats while we were on vacation. She did a great job and sent us pictures of her visits and play time. Upon returning home house ... (more)"

Confirmed availability
This weekend
9. Brooke

I looooveee all the pups!

Winchester, VA, 22603

House Sitting, Drop-In Visits, Dog Walking

"Brooke has a big heart and loves all animals, especially dogs and cats! She has a sunny disposition and is a hard worker, great communicator, and is very rel... (more)"

Confirmed availability
4th of July
10. Noah

I am willing to play with your dog!

Winchester, VA, 22603

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

"Noah is an extremely responsible young adult. He is conscientious and caring in all that he does, so you can rest assured that your pet family member is in ... (more)"

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11. Ali

Huge animal lover

Winchester, VA, 22604

Drop-In Visits, Dog Walking

About: I’ve been volunteering at my local animal shelter for 4 years so I have experience with all sizes and all kinds of dogs. I’ve walked and played wit... (more)

Confirmed availability
4th of July
12. Amber

Let me love your pups!

Winchester, VA, 22601

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

"Amber is a very pleasant, responsible, and trustworthy person, and has a deep affection for animals. If I ever need a dog sitter, she will be the first perso... (more)"

13. Shelby

Your pup's new running pal!

Winchester, VA, 22602

House Sitting, Drop-In Visits, Dog Walking

"Shelby has house/dog sat for my family on several accounts. She is a responsible, active young women who will not let you down. She pays close attention to... (more)"

Confirmed availability
This weekend
14. Anders

Home on 8 acres fulltime.

Clear Brook, VA, 22624

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

"Anders has watched both my doberman and mastiff several times. They enjoy both relaxing on the deck or playing fetch on the huge property with Lucy, his fami... (more)"

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15. Virginia

Growing up, we have always had dogs

Frederick, MD, 21702

Drop-In Visits, Dog Walking

About: I make myself available early in the morning and middle of the day. Growing up, my family has always owned dogs and I have considered them to be fa... (more)

Confirmed availability
4th of July
16. Terry

Must love dogs caretaker

Clear Brook, VA, 22624

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

"Terry's Pet Sitting is without question a wonderful resource! Her personal attention to each and every pet is exquisite! We used to take our pets to the kenn... (more)"

17. Karen

Dog Lovers Home away from Home !

Winchester, VA, 22602

Drop-In Visits

About: I first had a full time puppy from the leader dog program, who eventually became my long time pet for 14 years. I have a great fondness for othe... (more)

18. Adrienne

Home full-time

Winchester, VA, 22601

Drop-In Visits, Dog Walking

"I believe it is true, pets know a good heart! Adrienne lights up when she sees any dog and if one is near her, they immediately positively respond with jump ... (more)"

19. Diana

I will take daily walks with pets

Winchester, VA, 22601

House Sitting, Drop-In Visits, Dog Walking

About: I have a full time job currently, and i would be able to fit to the providers needs. I am looking to take care and help those in need with there a... (more)

Confirmed availability
4th of July
20. Shelley

Home full time

Clear Brook, VA, 22624

Drop-In Visits, Dog Walking

"Shelley is a great lady! Always on time, always reliable. I would leave my fur baby with her anytime and not worry at all. It definitely shows that she is a ... (more)"


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Stephenson pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Stephenson, VA, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Stephenson pet sitters and avoid the kennel.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.