Doggy Day Care in Chester, MD

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

Confirmed 4th of July Availability
1. Ashley

Stay at home Mom and animal lover!

Annapolis, MD, 21409

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

"I can’t say enough good things about Ashley! We found her on rover when we desperately needed a sitter for a few weeks. Ashley instantly accepted and started... (more)"

2. Jack

Large Fenced Yard + Home Full-Time!

Arnold, MD, 21012

Dog Boarding, Doggy Day Care

"Daisy had such a good time. She did not want to leave when I came to pick her up. I felt comfortable leaving her there even with her health needs. (more)"

Confirmed 4th of July Availability
3. Michelle

Beautiful back yard for your dogs!

Annapolis, MD, 21409

Dog Boarding, Doggy Day Care

"Michelle was excellent. She’s very sweet and has a beautiful yard for my dog to play in. she sent me updates and pictures daily and Gigi was really happy and... (more)"

Confirmed 4th of July Availability
4. Megan

Home Full Time - Ready to help

Edgewater, MD, 21037

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

About: I love animals, all animals! I am available to assist you with animal care needs. From dog walks to boarding, just give me a shout! I attend Dog ... (more)

5. Julie

'MUST LOVE DOGS'

Edgewater, MD, 21037

Dog Boarding, Doggy Day Care

"My canine kids had a great play day at Julie's. Will book again when I need a sitter in the future. (more)"

6. Kimberly

Home full-time

Arnold, MD, 21012

Dog Boarding, Doggy Day Care, Dog Walking

"I have known KIm for roughly 8 years. She has been the best neighbor! She has taken great care of my dog and watched out for my house. She and her family h... (more)"

7. Maegan

Dog lover! Experienced care

Annapolis, MD, 21401

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

"Maegan is a very trustworthy person that is always gladly willing to look after your dog. She always takes care of my dogs as much as she would to her own. M... (more)"

Confirmed 4th of July Availability
8. Veronica

The Best For Your Best Friends

Arnold, MD, 21012

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

"Great care for my dog and Lots of updates. (more)"

9. Megan

Work from home, love dogs

Annapolis, MD, 21401

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

About: I grew-up with dogs in my family and adored every minute I spent playing with them, running outside with them and enjoying their fun, loving nature... (more)

Confirmed 4th of July Availability
10. Sydney

Owner and Lover of dogs

Annapolis, MD, 21403

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

"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)"

11. Lindsey

Your pet's home away from home

Edgewater, MD, 21037

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

About: I work from home with my two fur babies, Dewey (doggy) & Keiki (kitty) and we would love your pet to join our zoo! We recently moved to Edgewater f... (more)

12. Neal

Dog love to run/hike? Perfect!

Stevensville, MD, 21666

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

"We left our 11 month old boxer puppy, Tootsie, with Neal for the day. He played with her during the day, took her on hikes and wore her out. He also sent us ... (more)"

13. Julia

Tons of fun for your pup!

Annapolis, MD, 21403

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

About: I am a teacher, and over the summer, I am home full-time and I would LOVE some company from your furry friend! I live next to a park and the water... (more)

14. Audreanna

Home full time, fenced in yard

Centreville, MD, 21617

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

About: I am basically a stay at home mom. I work one day a week at a dog grooming salon, I am a pet stylist! I have always loved working with dogs and I s... (more)

15. Ashley

Experience animal caretaker

Annapolis, MD, 21403

Drop-In Visits, Doggy Day Care, Dog Walking

"Ashley is a caring and attentive sitter. My dear Flower loved playing with Ashleys sweet Penelope dog (more)"

16. Lauren

Fur baby lover

Annapolis, MD, 21401

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

"Lauren was excellent and took wonderful care of Lady Bug. I will definitely reach out to her again. (more)"

Confirmed 4th of July Availability
17. Chelsea

Animal lover - home for the summer

Annapolis, MD, 21403

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

About: Hi there! I am passionate about all animals and have been surrounded by both dogs and cats my whole life. I grew up with golden retrievers and labr... (more)

18. Vicky

Nurturing family environment

Annapolis, MD, 21401

Drop-In Visits, Doggy Day Care, Dog Walking

"Vicky is an exceptional, responsible, and loving caregiver. Vicky definitely has lots of experience caring for animals. My dog Miami always has such a gre... (more)"

19. Victoria

"Lover of Fur Babies"

Annapolis, MD, 21401

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

"Victoria is a responsible, caring and kind person. I highly recommend her services as my dog just loves her! You can count on Victoria 100% always! Roberta V. (more)"

20. 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)"


With Rover, you can find a trustworthy, loving pet sitter to take care of your dog while you're at work or have a day full or errands. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 40,000 sitters who've listed their services on Rover. That way, you're sure to find a doggy day care who's right for your needs. We're proud that 95% of our sitters have 100% 5-star reviews, and we think your dog will love them too. Search for a sitter who offers doggy day care, schedule a Meet & Greet, and book the stay if it seems like a good fit. No matter how often you need day care, you're sure to find a sitter who will treat your dog like family.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.