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, Dog Walking

6 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. 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 Thanksgiving Availability
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

4 repeat clients

"She was amazing and flexible!! Bentley loved her!!!! (more)"

Confirmed Thanksgiving Availability
5. 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)"

6. Becca

Experience caring for all 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)"

Confirmed Thanksgiving Availability
7. 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)"

Confirmed Thanksgiving Availability
8. Wendy

Walk and Play with your dog.

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

3 repeat clients

"Wendy is a great dog-sitter, and cares about the welfare of each animal entrusted to her. When we had to go out of town and our dog was not feeling well, sh... (more)"

9. 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)"

10. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Jennifer did drop in visits with and my pups. They loved her. She came to meet our dogs before our trip and asked a lot of great questions. She reached out... (more)"

Confirmed Thanksgiving Availability
11. Mary

Sitting by Mary

Annapolis, MD, 21403

Dog Boarding, 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)"

12. Hanna

I love long walks on the beach

Annapolis, MD, 21403

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

"Hanna is an excellent dog sitter. She is very compassionate and empathetic so she takes great care. She is very responsible and mindful, so you can leave you... (more)"

Available this weekend
13. 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)"

14. Caitlin

flexible student who loves animals

Arnold, MD, 21012

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Caitlin has been sitting for our dog for the past couple years and he positively adores her. She's clearly a big animal lover and always gives him extra spec... (more)"

Confirmed Thanksgiving Availability
15. 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)"

16. Justine

Walk, Fetch, Groom, Relax

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"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)"

Confirmed Thanksgiving Availability
17. Madison

Dependable Doggie Sitter/Walker :-)

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"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)"

Confirmed Thanksgiving Availability
18. Sydney

Owner and Lover of dogs

Annapolis, MD, 21403

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

1 repeat client

"Sydney is phenomenal with animals. She's helped me out on multiple occasions with my Husky and Weimaraner and I've been more than satisfied every time! (more)"

Confirmed Thanksgiving Availability
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 Thanksgiving Availability
20. 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)"

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.