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 President's Day Availability
1. Wendy

Walk and Play with your dog.

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

11 repeat clients

"Wendy is so impressive, as a person and a dog sitter! From the moment you meet her she is warm and personable...she understood our needs and was eager to com... (more)"

2. 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)"

Available this weekend
3. Kate

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

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"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)"

4. Allie

Wagging for walks! Dog lover/owner

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"Allie was amazing! She took detailed pictures and kept me in the loop with everything going on with my pup. Will definitely contact her in the future!! :) (more)"

Confirmed President's Day Availability
5. Sydney

Owner and Lover of dogs

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Sydney always took great care of my pets and was super quick with responding to texts and calls and could always help at the last minute. Would highly recomm... (more)"

Confirmed President's Day Availability
6. 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 President's Day Availability
7. Caroline

Happy pet , happy life !!!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

3 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)"

Confirmed President's Day Availability
8. Sarah

Your pet's new best friend!

Annapolis, MD, 21409

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

"Sarah is very professional, communicative, always on time, and above all, great with my dog. She sent pictures and text messages to keep me "in contact" with... (more)"

9. 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)

10. 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)"

11. 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)"

12. 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

"He is very responsible, and love to have animals around him. He love to take dogs to trail. Also he always keep house clean. Neal is fun person. fun facts ab... (more)"

13. 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)"

Available this weekend
14. 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)"

15. Mackenzie

Ill treat your dog as my own

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"I have know Mackenzie for over 10 years and she’s always been loving and caring towards any animal . She has walked my shepherd mix chessie multiple times an... (more)"

16. Madison

Dependable Doggie Sitter/Walker :-)

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Madison took great care of our puppy, she was very responsible and took many pics. She stayed at our house for two nights and did a phenomenal job, can’t wa... (more)"

17. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"This was my first time using Jen or anyone on Rover. She did a drop in visit. She texted me with updates, which was a relief. She made me comfortable in kno... (more)"

18. 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)"

19. 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)"

Available this weekend
20. 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)"


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.