Pet Sitting & Drop In Visits in Winston Terrace, VA

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

Confirmed availability
President's Day
1. Leah

I’ll go the extra mile for your dog

Williamsburg, VA, 23188

House Sitting, Drop-In Visits, Dog Walking

"I thought she was great. My dog seemed to like her and she came at the times I asked and gave me an update. She helped me with the website and was very resp... (more)"

Confirmed availability
President's Day
2. Jessica

I’ll run and hike with your dog.

Williamsburg, VA, 23187

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

"Jessica was awesome! I contacted her the day before I made plans and she did as she said she would. She checked in with me. Shared pics. It’s such a great re... (more)"

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3. Caroline & Bob

Caring grad students - love animals

Williamsburg, VA, 23185

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

"Zoey loved Caroline abs (more)"

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4. Michaela

College student with too much time!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Michaela is such a wonderful and kind person! I’ve known her for a little over 3 years and can assure that she is a very responsible and caring person! She h... (more)"

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5. Joseph

Happy when your dogs are happy.

Williamsburg, VA, 23185

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

"Joey has always been extremely sweet and loving to my dogs. I have three dogs, two small and one large, and they can be wary of new people, especially men. ... (more)"

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6. Josue

Dog Walking Archaeologist!

Williamsburg, VA, 23188

Drop-In Visits, Dog Walking

"Always prompt and responsible. Thank you. (more)"

Confirmed availability
President's Day
7. Laura

caring, kind and attentive doglover

williamsburg, VA, 23188

House Sitting, Drop-In Visits, Dog Walking

"Laura is kind-hearted, responsible, compassionate, patient, and is easy to get along with, and I fully trust her as a dog sitter. My family has two small pap... (more)"

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8. Stephanie

Home full time, lots of exercise

Williamsburg, VA, 23185

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

"Stephanie was wonderful! She was extremely comfortable handling our two big hyper goofballs and we couldn’t be more pleased with that! (more)"

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9. Grace

W&M Student Pet Care

Williamsburg, VA, 23188

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

About: I am a college student at William & Mary who will be in Williamsburg from May through the end of July taking classes part-time. I am able to be ho... (more)

Confirmed availability
President's Day
10. Amanda

MBA, active life, missing my dogs!

Williamsburg, VA, 23185

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

About: Hi! I graduated from Cornell University as an Animal Science major. As a freshman, I joined the service dog training program, Guiding Eyes for the... (more)

Confirmed availability
President's Day
11. Kelsey

Will love your dog like my own

Williamsburg, VA, 23185

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

"Kelsey was great. Very accommodating. Thank you. (more)"

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12. Jessica

Experience with many breeds

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Jessica is truly a dog lover. The love she has for dogs, and all animals, shines through on a daily basis. She treats her family dog like he really is a par... (more)"

13. Erika

I Will Treat Your Pet Like My Own!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Erika was absolutely great with our pets! Having a diabetic dog makes us nervous to leave him...and eat to expensive to board. Erika provided the exact care ... (more)"

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14. Greta

super flexible animal loving gal!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Last summer, from May to July, Greta took care of our dog Anio. She watched him 3 times a week as well as a few weekends. At this time, he was only 6 months ... (more)"

Confirmed availability
President's Day
15. Cody

Ready to get outside with your dog!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Cody is so great with dogs! He has cared for my pups when I’ve gone away on vacation. He is the perfect belly scratcher as well as walker. Cody makes sure to... (more)"

16. Emily

Animal Care Specialist and Lover!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"I have a special needs senior dog and Emily was great with her! I felt very confident that she could handle any problems that might come up. (more)"

17. Bryan

I’ll be your dog’s cool uncle

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Bryan has lovingly cared for my cat and, in addition to meeting the cat's physical needs and picking up my mail, Bryan spends quality time with my cat provid... (more)"

Confirmed availability
This weekend
18. Emma

Home full time, loves to play!

Williamsburg, VA, 23185

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

"Emma took excellent care of my cat. She made the entire experience smooth and seamless—from stopping by to meet my cat before I left to sending photos from e... (more)"

Confirmed availability
This weekend
19. Melissa

"Your Dog Is My Houseguest."

Williamsburg, VA, 23188

Dog Boarding, Drop-In Visits

"Melissa cared for our dogs over a holiday weekend and we had no complaints! She kept us updated after every drop in visit and sent pictures as well! Our dogs... (more)"

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20. Alexandra

Dog lover at your service!

Williamsburg, VA, 23188

House Sitting, Drop-In Visits, Dog Walking

"Loves, loves dogs! Very patient and caring with all animals. Dependable to stay on task and get it done right. Understands that our dogs are not just pets bu... (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 Winston Terrace 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 Winston Terrace, 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 Winston Terrace pet sitters and avoid the kennel.