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.

Tip: Contact sitters now to confirm availability.
1. Erica

Where pets are family

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"I was so nervous about leaving my new puppy during the day! Erica is fantastic and very responsive! Both my older dog and new puppy are in great hands! (more)"

Confirmed availability
4th of July
2. Ashley

Stay at home Mom and animal lover!

Annapolis, MD, 21409

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

"Ashley is an excellent person to take care of animals. She loves all types of animals. I would highly recommend ashley to walk or pet sit. (more)"

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3. Ashley

Pet Care When You're Not There!

Annapolis, MD, 21409

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

"Ashley loves dogs. She doesn't care about their size, breed, nor age. She plays with any dog she comes across. She has owned dogs for as long as I have kn... (more)"

4. Kate

Must love dogs...Yes, that's me!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Kate was fantastic watching our two pups. She was quick to respond when I put in the initial request, and was able to come do a meet and greet right away. Ka... (more)"

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5. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

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

"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)"

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6. Caroline

Happy pet , happy life !!!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Caroline is awesome! She always seems very in tune with Sully and what he wants and needs. She gives detailed feedback about their time together and that mak... (more)"

Confirmed availability
4th of July
7. Kristin

Love All Dogs!

Queenstown, MD, 21658

Dog Boarding, Drop-In Visits, Dog Walking

About: I absolutely love dogs and have two doodles of my own! I've taken care of dogs as small as a maltese and as large as a doberman. I used to watch do... (more)

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8. Julia

I will love your dog like you do!!!

annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Julia watches my husky chelsea all the time and always takes such good care of her. She’s very attentive and always gives me frequent updates. Would reccomen... (more)"

Confirmed availability
4th of July
9. Rachel

Professional Experience with AWL

Stevensville, MD, 21666

House Sitting, Drop-In Visits

"if you're looking for someone to love and watch over your pets while you're away, it's definitely Rachel! She has a HUGE heart for animals. She has taken gr... (more)"

10. Leah

Flexible, Will be BFFS w/ your dog!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Leah, was an excellent loving, dependable dog sitter. My dog Ellie normally does not eat when we go away but she did for Leah. That means Ellie was comforta... (more)"

Confirmed availability
4th of July
11. Stephanie

Love all dogs and breeds

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Stephanie is great with animals. She treats them with the love and respect that she shows towards her own dog. She watched our dog multiple times and I alway... (more)"

Confirmed availability
This weekend
12. Megan

A smile and a wagging tail!

Stevensville, MD, 21666

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

About: Loving and caring pet sitter! I have had dogs all my life, I am an absolute animal lover. I use to be a volunteer at ARF and have also helped my si... (more)

13. Neal

Dog love to run/hike? Perfect!

Stevensville, MD, 21666

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

"I've worked with Neal the last few years and found him to be a hard and open worker. He will ensure the safety and comfort of your pets and ask questions whe... (more)"

14. Celia

Don't stop retreivin'

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

About: I grew up learning how to walk by holding onto my German Shepard's tail. I've always been around animals for as long as I can remember. I've had li... (more)

15. Kelli

Dog lover! Home full-time

Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Fiona is family. Kelli is family. And they love each other. Kelli only recently moved but when she was living here she was always ready and willing to watch ... (more)"

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16. Rozzie

Responsible & Caring Pet Services

Annapolis, MD, 21409

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

About: I am a professional Pet Sitter and I will take care of your pets as if they were my own...I am very flexible and will do everything possible to mee... (more)

17. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

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

"NorH took care of my pugs without any problems. We are happy to have found her and appreciate her last minute help to have carefor the pups. (more)"

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18. Samantha

Flexible schedule and active!

stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Samantha is great! She is responsible, dependable and caring. She clearly loves animals and enjoys what she does. Our two dogs are always very excited to see... (more)"

Confirmed availability
4th of July
19. Callie

Live, Love, Bark!

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

"Usually I am skeptical about leaving Sasha, my two year old husky with a sitter due to her separation anxiety(on top of her off-the-chain energy levels) but ... (more)"

Confirmed availability
4th of July
20. Kathleen

Your dog's safety is my priority!

Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Kathleen has been a trusted and responsible employee of Animal Resource Foundation (ARF) since 2010. Over the years Kathy has proved to be dependable and he... (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 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.