Pet Sitting & Drop In Visits in Chester, MD

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

1. Faelyn

I'll love your dogs like my own!

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

"Faelyn is a great help with our two puppies! They need to be let out a couple times during the day and get lots of exercise. They seemed to like her the inst... (more)"

2. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

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

2 repeat clients

"Janet was great! She appears to have taken great care of the dogs, and sent pictures at every visit. She even made one extra, last minute stop when our fligh... (more)"

3. Layne

Home full-time. Large fenced yard.

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

"Layne is one of the sweetest people I've ever met and she is the biggest dog lover i know. She grew up with dogs and has always treated every dog as her own ... (more)"

4. Hannah

Experienced and reliable dog lover!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

About: I will be a sophomore this upcoming year at James Madison University and am looking for some dog sitting/ walking jobs before I go back to school i... (more)

5. Becca

Experience with many animals!

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

1 repeat client

"Becca is one of the bests, if not the best sitter we have ever had! She is wonderful with our dog Felix. One week of working with her was a real breeze. She ... (more)"

6. Christa

Love long walks-larged fenced yard!

Annapolis, MD, 21409

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

About: I absolutely adore all dogs! We currently have an 11 month old pug who is our entire world and I would love to help out others by walking their pup... (more)

7. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Everything went great. Jennifer showed up on time and left several pictures each time, which I loved. She exercised my pups and they were happy campers. W... (more)"

8. Mary

Sitting by Mary

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Mary was wonderful! She was very responsive and very easy to book last minute. She took good care of Hunter and I will be definitely be booking her again. (more)"

9. Sarah

Flexible and Reliable Sitter

Arnold, MD, 21012

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Sarah did an incredible job despite Emma having a medical issue. Was extremely prompt and kept me in the loop during her time with Emma. Emma had a faintin... (more)"

10. Izabella

Very Flexible schedule for dog care

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Izzy has taken care of my dogs for past few years when I travel! She also worked for me at my business for 2 years. She very responsible and dependable and i... (more)"

11. Justine

Walk, Fetch, Groom, Relax

Stevensville, MD, 21666

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

1 repeat client

"Justine was great. Did exactly what I ask, showed up when promised and was great with my dog. Would highly recommend her! Brian H Stevensville MD (more)"

12. Amy

Your pooch is gonna love me!

Queenstown, MD, 21658

Drop-In Visits, Dog Walking

About: Hi! I am a mom of 3 human kids, 2 canine kids (Jackson - Bernese Mountain Dog, Phoebe - English Bulldog), 2 feline kids, 2 fish and 4 hermit crabs!... (more)

13. Taylor

Energetic and Experienced Care

Chester, MD, 21619

House Sitting, Drop-In Visits, Dog Walking

"Taylor is responsible, caring and each dog she has encountered instantly falls in love with her. I can go away for a weekend knowing my sweet Annabelle is in... (more)"

14. Carlie Rose

I'll love every dog like my own

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"I have been using Carlie for about three months now. She has done nothing but exceeded my expectations. She is the type of girl who cant help but go out of ... (more)"

15. Rozzie

Flexible Caring Dog Walker / Sitter

Annapolis, MD, 21409

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

About: I will take care of your pets as if they were my own...I am very flexible and will do everything possible to meet any needs and requests you may ha... (more)

16. Jesse

Dog Lover Sits in YOUR Home

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"tp start off Jesse is a very kind and loving person. He loves dogs and is currently taking care of both of mine while I am away in college. he has taken care... (more)"

17. Kareen

Animal Lover

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

1 repeat client

"We have used Kareen several times to take care of our loving dog Oscar when we've been on vacations or during the day if we were hung up with work or other c... (more)"

18. Emma

Young/energetic recent college grad

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: Hello! I am a recent graduate from York College of Pennsylvania. I studied marketing and graphic design while I was there. While I was there I was ... (more)

19. Kate

Dog Lover Who Will Spoil Your Dog!

Stevensville, MD, 21666

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

"My name is Alex, and Kate pet sat for my wife and I while we were out of town. We had a meeting ahead of time so our dog could get to know her and they seeme... (more)"

20. Ashley

I am available to watch your pups!

Grasonville, MD, 21638

Drop-In Visits, Doggy Day Care, Dog Walking

"Ashley is an amazing mom to her own pets as well as the foster puppies she has cared for in the past. She is always taking them on walks, buying them treats... (more)"

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Learn About Premier

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 Chester 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 Chester, MD 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.