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. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

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

4 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)"

2. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

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

"I have known Norah for many years and found her to be a hard and open worker. She will ensure the safety and comfort of your pets and ask questions when need... (more)"

3. Kelli

Home full time, large fenced yard

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

1 repeat client

"Kelli took great care of Boomer with two drop-in visits. Boomer is only 13 weeks, so schedule and details are key in getting her house trained. Kelli kindly... (more)"

4. Kate

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

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Katie rocks. Quick to respond. Takes care of business. Very friendly. Recommend ???? (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. Sarah

Flexible and Reliable Sitter

Arnold, MD, 21012

House Sitting, Drop-In Visits, Dog Walking

17 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)"

7. Lena

Dog Lover For Your Doggie needs!

Arnold, MD, 21012

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: Hi there! My name is Lena and I'm a dog walker and pet sitter. I'm 30 years old and have been working in this field for the last nine years. I star... (more)

8. 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)"

9. 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)"

10. Madison

Dependable Doggie Sitter/Walker :-)

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Madison house sits and takes care of my 3 dogs and hamster all the time!! Super reliable and very experienced with animals. Always more than pleased!! (more)"

Available this weekend
11. Maria

Satisfaction Guaranteed Home & Pet

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Maria Really knows how to handle dogs. Normally my 90lb black lab takes me for a walk. But when Maria stops by for his afternoon walks, he is on his best beh... (more)"

12. Rachel

Professional Experience with AWL

Grasonville, MD, 21638

House Sitting, Drop-In Visits

About: I've grown up with a lot of pets; cats, dogs, guinea pigs, a ferret, rats, hamsters, and chickens have all been companions in my home at some point... (more)

13. 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)"

Available this weekend
14. 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)"

Available this weekend
15. 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)"

16. Adrianne

Time to walk the dog!

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

About: As a child I had a dog. Then helped love 3 rescued greyhounds. Now helping with 2 rescued dachshunds. I like interacting and playing with dogs and ... (more)

17. 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)

18. Angie

I'm Purrrfect for your Pet!

Arnold, MD, 21012

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

"My cat, Bert gets so excited when he gets a visit from Angi. She has established a special connection with him. She loves animals and exercise, so what a per... (more)"

19. 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)"

Available this weekend
20. Rozzie

Responsible & Caring Pet Service ?

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)

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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.