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.

1. Lisa

Doggo-loving and 30-something!

Williamsburg, VA, 23188

Drop-In Visits, Dog Walking

"Lisa was so great with my babies! She sent me updates and had no issues during her time with them. My dog can be a little difficult at times, but he seemed... (more)"

2. Mary

Your Rover's Home Away From Home

Williamsburg, VA, 23185

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

"I have been friends with Mary for 30+ years. She is caring, compassionate, thoughtful and considerate. She and her family have always had pets, and even thou... (more)"

Available this weekend
3. Jessica

Loves spending time outdoors

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Prior to being hired Jessica spent time learning about our dog and was attentive to her needs. While we were away, she communicated with us daily, sending t... (more)"

4. Melissa

"Your Dog Is My Houseguest."

Williamsburg, VA, 23188

Drop-In Visits

"This was first time using a dog sitter while on vacation and Melissa exceeded our expectations. She checked in regularly with updates after every visit and ... (more)"

5. Katherine

Dog Lover

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Katherine was very diligent in her notes and sent many photo updates as well! Very thankful for her drop-ins with Remy. (more)"

6. Josue

Dog Walking Archaeologist!

Williamsburg, VA, 23188

Drop-In Visits, Dog Walking

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

7. Erika

I Will Treat Your Pet Like My Own!

Williamsburg, VA, 23185

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

"Erika is the best. We totally trust her and know our pets will not only be taken care of, but loved on while we are gone. She's responsible, genuine & your p... (more)"

8. Leah

I’ll go the extra mile for your dog

Williamsburg, VA, 23188

House Sitting, Drop-In Visits, Dog Walking

"I have known Leah for years and she has always had a fierce love of dogs! She has watched my corgi for me more than a few times and gladly helps if and when ... (more)"

9. Shalynn

Girl & a dog looking for playmates

Williamsburg, VA, 23188

Dog Boarding, Drop-In Visits, Dog Walking

"We used Shalynn for drop in visits, she was perfect. She was able to fit us into her schedule on short notice. She was very sweet to our puppy and sent me ad... (more)"

10. Caitlin

Dogs love me!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

About: I am an experienced pet sitter and am kind, caring, and responsible. I love all animals, especially dogs! I was a vet tech for one year at Godspeed... (more)

11. Candice

I have a genuine heart for dogs!

Williamsburg, VA, 23185

Drop-In Visits, Doggy Day Care, Dog Walking

"I wanted to extend kindest words about Candice as she has been an absolute blessing to me. She has gone above and beyond in her services for me. I tell her ... (more)"

12. Rachel

I love to play & walk/run with dogs

Williamaburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Rachel is awesome with dogs. She watched my dog Stevie during the day while I was at work, and was very attentive with her needs. She took Stevie to the dog ... (more)"

13. Heather

Loves animals of all kinds

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Heather is kind, personable, and responsible. I felt comfortable leaving her in care of both my home and pets, knowing they would get the love and attention ... (more)"

14. Drew

I'll keep your dog happy!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"I had a very good experience with Drew. He was flexible in coming to get the keys, dropping them off, and when to visit the cat. As far as cat sitters go, es... (more)"

15. Kristina

Your dog will love me!

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Gracie and Riley love Kristina! She's so good with them. She loves taking them for walks and playing with them and treats them like they were her own puppies... (more)"

16. Midori

Love outdoors, will run & play.

Williamsburg, VA, 23188

House Sitting, Drop-In Visits, Dog Walking

"Midori is one of the most responsible people I know. She loves animals and would do anything to ensure their happiness and safety. When I got my puppy Midori... (more)"

17. Jordan

Let me take your dog for the day

Williamsburg, VA, 23185

House Sitting, Drop-In Visits, Dog Walking

"Jordan has always been great with animals! Everytime he comes over he seems to pay more attention to my dogs than me. Jordan has a great personality and is v... (more)"

18. Elizabeth

Williamsburg Staycation

Williamsburg, VA, 23188

Dog Boarding, House Sitting, Drop-In Visits

"Elizabeth was great! She showed complete love and attention towards our animals! She was very interactive and caring with our labdor, and she was even able... (more)"

19. Grace

W&M student summer dog 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)

20. Julia

Professional and caring pet sitting

Williamsburg, VA, 23188

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I'm your neighbor you can count on to help you while you are away. I have strong community ties to Williamsburg, so you count on me to love... (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.