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.

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1. Michelle

Beautiful back yard for your dogs!

Annapolis, MD, 21409

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

"Michelle was great! Very easy to communicate with and I love that she sent me pictures to show me how Coco was doing. (more)"

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2. 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)"

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3. Jack

Large Fenced Yard + Home Full-Time!

Arnold, MD, 21012

Dog Boarding, Doggy Day Care

"ADDIE looks forward to her stays with Jack and his family, her tail starts wagging away as soon as she jumps out of the car and sees where she is at. Jack is... (more)"

4. Pam

I love animals!

Shady Side, MD, 20764

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

"Pam took lovely care of our golden retriever Moose over the holiday weekend. She was very accommodating and even offered to pick up and drop off Moose. She k... (more)"

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5. Haley

Dogs Are My Kind Of People :)

Annapolis, MD, 21403

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

"Haley helped us last minute and it was a great relief for us to find someone who we could trust to take care of our mini Schnauzer while we toured The Naval ... (more)"

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6. Mary Ellen

Home away from home for your dog

Annapolis, MD, 21403

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

"Mary Ellen is one of the most caring dog owners I have ever known. She adopted a very senior Pekignese in addition to her cavalier mix and has provided wonde... (more)"

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7. Megan

Home Full Time - Ready to help

Edgewater, MD, 21037

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

"Megan C took care of my golden retriever Elvis and we went to a meet and greet to meet her dog Roxy and it was love at first sight. When we picked up Elvis h... (more)"

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8. Shacja

5-acre waterfront fenced property

Annapolis, MD, 21409

Dog Boarding, Doggy Day Care

"Janet is a warm and friendly person with a genuine love for dogs. She has an adorable Boston terrier named Heidi and Heidi gets lots of tender loving care f... (more)"

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9. Meghan

I am home full time love animals

Pasadena, MD, 21122

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

"Meghan loves animals. She is very compassionate and has taken excellent care of my dog Chloe when I go out of town. She would be an excellent choice to take ... (more)"

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10. Kimberly

Home full-time

Arnold, MD, 21012

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

"Kim is a genuine and compassionate person. She is a dedicated mom of four great kids. Their family pet includes a beloved sweet yellow lab named Oddie. I ... (more)"

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11. Carolina

“ Play, eat, nap, repeat!”

Annapolis, MD, 21409

Dog Boarding, Doggy Day Care

"Carolina loves dogs and is very responsible. I love that she will send you pictures and updates to see how your pup is doing. Communication with her is easy ... (more)"

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12. 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)

13. Laurie

Kent Island fenced yard! Home 24/7

Stevensville, MD, 21666

Dog Boarding, Doggy Day Care

"I have searched a very long time for a pet sitter like Laurie. I have a 16 year old dachshund that loves to snuggle and be loved on. When we left for two wee... (more)"

14. Christa

Fenced yard+photos+walks<3

Annapolis, MD, 21401

Dog Boarding, Doggy Day Care

"I couldn't have asked for better accommodations! My Labrador was very well cared for and Christa is very well versed in how to acclimate your pet. Plenty of ... (more)"

15. Marlene

Fun Loving Pet Caretaker

Annapolis, MD, 21409

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

About: Hi, my name is Marlene and I truly enjoy caring for pets. I am looking for extra income during the summer months while on break from working in sch... (more)

16. 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)"

17. 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)"

18. 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)

19. Rebecca

I love being a caretaker for dogs.

annapolis, MD, 21403

Drop-In Visits, Doggy Day Care, Dog Walking

"Rebecca has always loved dogs. She is the one who wanted to adopt rescue animals....which we have done for all of our dogs. She takes care of Peaches an... (more)"

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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.