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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. John

Lifetime of pet care!

arnold, MD, 21012

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"John was great with our standard poodle, Gracie. He visited twice a day and she did very well. Absolutely none of the usual destructive behavior she's shown... (more)"

2. Lori

Lover of animals big and small

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

1 repeat client

"This was my first Rover experience, and we were extremely pleased with Lori's services. Would highly recommend her and will certainly use her in the future!... (more)"

3. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

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

"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)"

4. Mitchell

US Navy Police Officer. Dog lover!

Annapolis, MD, 21402

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Mitchell took great care of my dog while I was away for the weekend. He kept me updated with texts and a few pictures. I didn't worry at all while I was go... (more)"

5. Jessica

It's ok, my dogs my best friend too

Annapolis , MD, 21401

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

8 repeat clients

"My first time using Rover, and Jessica made it so simple to coordinate. She was great with my pup, and put my mind at ease. Thanks again! (more)"

Confirmed Holiday Availability
6. Heather

I will love your pet like they are

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Heather is one of the most compassionate people I've ever met! She loves animals of all kinds and would do anything in her power to make sure they're safe an... (more)"

7. Heidi

I have a huge heart for pups!

Annapolis, MD, 21401

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

6 repeat clients

"Heidi was my top Puppy Nanny working for me in Chicago, IL. She cared for all of our furry clients as if they were her own! Heidi handled In Home Pup Sitti... (more)"

Confirmed Christmas Availability
8. Justine

Walk, Fetch, Groom, Relax

Stevensville, MD, 21666

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)"

9. Morgan

Biologist Who Loves All Animals

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

About: I have had a family dog for over 12 years. He is a Shar-pei, and prone to health problems so I have experience with medicine regiments such as pill... (more)

10. Becca

Experience with many animals!

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"I don't trust anyone as much as I do Becca to watch over animals. She has ample experience with all kinds of animals, not just dogs. She cares for every pet ... (more)"

11. Amy

Your pooch is gonna love me!

Queenstown, MD, 21658

Drop-In Visits, Dog Walking

About: Hi! I am a mom of 3 human kids, 2 canine kids (Jackson - Bernese Mountain Dog, Phoebe - English Bulldog), 2 feline kids, 2 fish and 4 hermit crabs!... (more)

12. Becky

Enthusiastic and fun-loving

Annapolis, MD, 21401

House Sitting, Drop-In Visits

About: I have always had a special relationship with dogs. Never mattered the type, just that I got to enjoy their company. In my own life, I've been luck... (more)

Confirmed Holiday Availability
13. Aleksandra

Playful energetic dog lover!

Stevensville, MD, 21666

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

About: Hello, my name is Aleks. I've had dogs my whole life, and always loved to babysit my friends animals. I love to interact with them like play fetch ... (more)

14. Jesse

Dog Lover Sits in YOUR Home

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"I have known Jesse since he was a teen. He has always been a very caring, gentle guy especially when it comes to animals. His family has had dogs for years... (more)"

15. Sarah

For the Love of Dogs <3

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"I am a lifelong dog lover and met Sarah 6 years ago as she was working at "The Canine Fitness Center" in Crownsville, MD. My dog Honey was rehabilitating an ... (more)"

16. Kareen

Animal Lover

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

1 repeat client

"We have used Kareen several times to take care of our loving dog Oscar when we've been on vacations or during the day if we were hung up with work or other c... (more)"

17. 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)

18. Clavis

Military Style Dog Watcher

Pasadena , MD, 21122

House Sitting, Drop-In Visits, Dog Walking

About: My dad has been in the United States Army for 20 years, and I have moved all across the United States.Through my travels I have had numerous pets, ... (more)

19. Ashley

I am available to watch your pups!

Grasonville, MD, 21638

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

"I've known Ashley for 12 years and she has such a love for all animals. Her dog Captain and cat Stella are so lucky to have her. She is always willing to dog... (more)"

20. Jill

Energetic, humble, and playful

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Jill was my labs favorite sitter (and ours too)! Jill will treat your pet as though it is part of her family. She sent us texts each day with pictures of o... (more)"

Experience exceptional service and a personalized match

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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.