Pet Sitting & Drop In Visits in Winston, 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

Fur babies are the best!!

Remington, VA, 22734

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Lisa was great! Very professional, responsive and thorough. I felt very comfortable having her care for my pack and will request her again for sure! (more)"

2. Kimberly

Pets are family too

Culpeper, VA, 22701

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

11 repeat clients

"Thank you Kimberly for providing such great care and peace of mind to enjoy our daughter's wedding! Having a young puppy and not many boarding options was s... (more)"

3. Erin

College student &lifetime dog lover

Rhoadesville, VA, 22542

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"She's is the best! Booking again! (more)"

4. Karen

Your dog will love me :)

Madison, VA, 22727

House Sitting, Drop-In Visits, Dog Walking

"We have trusted Karen with our dogs for nearly ten years. The first thing that impressed us was her concern for their dietary needs or special things not al... (more)"

Confirmed Holiday Availability
5. Amber

Home full time

Locust Grove, VA, 22508

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

About: I have currently transitioned to a stay at home mom from a second grade teacher. I am hoping to fill my days with sone animals to cate for. I love... (more)

6. Heather

Your Pups Health & Happiness is #1

Jeffersonton, VA, 22724

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

"Heather not only loves animals, she understands them. She has provided care for our dog on several occasions. I was confident that my pet was receiving the b... (more)"

Confirmed Christmas Availability
7. Noel

Love walking dogs and play time

Culpeper, VA, 22701

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

About: I’m 18 years old. My mother is a vet tech and I’ve been going to dog sitting jobs with her since I was around 13 and I loved helping her with it so... (more)

Confirmed Holiday Availability
8. Towner

“All my dawgs are dogs”

Rochelle, VA, 22738

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

"Towner P. Has been around dogs his entire life and loves them. He currently has a dog and spoils her rotten! He provides lots of love and exercise and vet ca... (more)"

9. Jennifer

Excellent Pet care.

Culpeper, VA, 22701

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

About: I have grown up always owning 1 dog and 2 cats, along with a reptile or two as well. Currently at my house, I own a large dog, 2 snakes, and a bear... (more)

10. Ronda

Worry free Pet care

Culpeper, VA, 22701

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Rhonda was awesome. She took excellent care of our dog and texted me every day. (more)"

Confirmed Holiday Availability
11. Shannon

Your dogs home away from home!!

Amissville, VA, 20106

Drop-In Visits, Dog Walking

5 repeat clients

"Shannon has cared for my dogs on several occasions. She has always done a great job! I highly recommended her and will definitely leave my dogs with her again. (more)"

12. Paige

I'll Play with the dogs

Bealeton, VA, 22712

House Sitting, Drop-In Visits, Dog Walking

About: I am 20 years old and have had dogs in my life for 15 years. I have 3 dogs of my own and love to play in the back yard with them. My 2 year old dau... (more)

13. Anna

Owned dogs my whole life

Culpeper, VA, 22701

Drop-In Visits, Dog Walking

"Anna is a great dog sitter! We have asked her to watch our dog Emory on several occasions, and Emory loves her! Anna does a great job taking Emory on walks... (more)"

14. Terr

TLC for your furry family member...

Boston, VA, 22713

House Sitting, Drop-In Visits, Dog Walking

About: Hello...My name is Terri. Animals have always had a huge presence in my life. I have volunteered at Animal Shelters and No-Kill Facilities in Vir... (more)

Confirmed Holiday Availability
15. ChristiAne

experienced, individualized petcare

Culpeper, VA, 22701

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Over 30 years experience taking care of dogs (and cats, and horses, and a few other species) as a pet sitter, veterinary technician, kennel attenda... (more)

16. Laura

100% Love and Attention

Culpeper, VA, 22701

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

7 repeat clients

"Laura cared for our dog, Violet, while we were gone on a family vacation for 11 days. I knew Violet would be loved and cared for and I didn't worry one bit... (more)"

Confirmed Holiday Availability
17. Geena

Caring and responsible animal lover

Culpeper, VA, 22701

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

"My husband and I have known Geena for several years now!! I gladly trust her in my house and with my fur-child at anytime and for any amount of time!! She ha... (more)"

18. Kelly

Compassionate worry-free pet care!

Culpeper , VA, 22701

House Sitting, Drop-In Visits, Dog Walking

About: I have grown up with dogs my entire life! I have 2 dogs, one sheltie and a mini Aussie who love to play and cuddle. Both of my dogs are rescuer... (more)

Confirmed Holiday Availability
19. Stephanie

College student doing what I love!

Locust Grove, VA, 22508

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I've owned a dog my entire life, at least one actually! I'm trying to make a little extra money spending time with animals. Couldn't think of a bet... (more)

Confirmed Christmas Availability
20. Jennifer

Eat, Play, Love, Rest, Repeat

Culpeper, VA, 22701

House Sitting, Drop-In Visits, Dog Walking

"Jenn is extraordinary with dogs and makes it look so easy. She is nothing less than a loving, wise, informed, humble, and joyous guru on the emotional well-... (more)"


As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Winston pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Winston, VA who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.