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.

Confirmed Memorial day Availability
1. Wendy

Walk and Play with your dog.

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

28 repeat clients

"This was our first time booking Wendy. She took care of our dog and cats over the Christmas holiday for a week. We felt very comfortable leaving our pets i... (more)"

2. Kayla

Love spending time with dogs!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Kayla did everything just as we instructed. She came on time and sent us messages and pictures. I would highly recommend Kayla. (more)"

3. Caroline

Happy pet , happy life !!!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"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)"

4. Erica

Where pets are family

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Erica does drop in visits for my dogs during the week, so I took the plunge and asked her to dog sit while I was away at a conference. She did a great job, a... (more)"

Confirmed Memorial day Availability
5. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

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

9 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)"

6. Kate

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

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Kate was wonderful with our two dogs! Harley is very hesitant with strangers and Moose is the opposite —a LOT of energy, and Kate was great with them! Defini... (more)"

7. Ashley

Pet Care When You're Not There!

Annapolis, MD, 21409

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

6 repeat clients

"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)"

8. Casey

certified veterinary assistant

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Casey is amazing - not only will she love your dogs when walking or puppy sitting but she also let's them go swimming in her puppy pool! My puppies love her ... (more)"

9. Nicole

My dogs are my life!

Stevensville, MD, 21666

Dog Boarding, Drop-In Visits, Dog Walking

About: I am a hard working mother who has a love for animals. I have a great personality and I am very easy to get along with. I have two of my own dogs w... (more)

10. Jenna

Home full-time and loves to play!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

About: I am currently employed as an elementary school substitute teacher and work part-time at the front desk of a yoga studio. At the moment my schedule... (more)

11. Victoria

Looking to love on all the animals!

Annapolis, MD, 21409

Dog Boarding, Drop-In Visits, Dog Walking

About: I love dogs and have been around them since I was little. The only reason I don't currently have a dog is because I don't have the funds available ... (more)

12. Callie

Live, Love, Bark!

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

13. Neal

Dog love to run/hike? Perfect!

Stevensville, MD, 21666

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

1 repeat client

"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. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

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

1 repeat client

"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)"

15. Kelli

Dog lover! Home full-time

Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Kelli is the best doggy care giver I could ever hope for!! Starting from when my pup, Mulligan, was a young puppy, Kelli has taken care of him. She always co... (more)"

16. 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)"

17. Rachel

Professional Experience with AWL

Stevensville, MD, 21666

House Sitting, Drop-In Visits

"I have known Rachel for her whole life. She is very sweet, honest and reliable. She loves animals like no-one I know. She would be a great asset to have work... (more)"

18. Carly

Reliable dog walker/ sitter!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Carly is an active outgoing dog walker. She loves being outside and enjoys taking my dogs on long walks. She has watched my dogs on numerous occasions while ... (more)"

19. 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)"

20. Jena

Experienced Pet Sitter 4+ Years

Grasonville, MD, 21638

Drop-In Visits, Dog Walking

About: My name is Jena, not only have I had pets of my own since I was little, but I have also owned a pet and house sitting business for the past 4 years... (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.