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 availability
Christmas and New Year
1. Ashley

Stay at home Mom and animal lover!

Annapolis, MD, 21409

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

"Ashley is attentive and a natural caretaker. She is an animal lover and it shows. My Tiana just loves her and her children. It has been a great experience to... (more)"

Confirmed availability
Christmas and New Year
2. 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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3. Haley

Dogs Are My Kind Of People :)

Annapolis, MD, 21403

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

"Haley,was grate! Her kindness and love for my dog showed. Sally could not stop talking about her new friends. Thank you, Sally&Terry (more)"

Confirmed availability
Christmas and New Year
4. Mary Ellen

Home away from home for your dog

Annapolis, MD, 21403

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

"I have known Mary Ellen for over 15 years. We have taken care of each other's dogs over those years and Mary Ellen is the best. I trust her completely with m... (more)"

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5. Jack

Large Fenced Yard + Home Full-Time!

Arnold, MD, 21012

Dog Boarding, Doggy Day Care

"Daisy always has such a great time at Jack's. She spent Saturday and Sunday playing at his house and she's still snoozing the day away Monday at almost 2. ... (more)"

Confirmed availability
Christmas and New Year
6. Justine

Dog Lover turned Sitter

Stevensville, MD, 21666

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

About: My name is Justine. I am 28 years old. I live on Kent Island in Maryland. I am currently going to school for my Master's at George Mason but the cl... (more)

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7. Kimberly

Home full-time

Arnold, MD, 21012

Dog Boarding, Drop-In Visits, 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)"

Confirmed availability
Christmas and New Year
8. Anthony

Home full time- Built in Dog Park

Arnold, MD, 21012

Dog Boarding, Drop-In Visits, Doggy Day Care

About: I'm the Dad of Adiline a 19 month old boxer & Odin a 7 month old American bulldog, boxer mix. I work from home my puppies are with me all day and l... (more)

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9. 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)"

Confirmed availability
Christmas and New Year
10. Stephanie

Dogs are part of our family

Annapolis, MD, 21401

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

About: I love dogs to the point i would let them sleep with me or share the sofa. I would go for a walk at downtown. We would go to the park and have ... (more)

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11. Carolina

“ Play, eat, nap, repeat!”

Annapolis, MD, 21409

Dog Boarding, Doggy Day Care

"Carolina loves her pup Coco and she will treat your dog the same way. She will go out of her way to make sure that your dog is having a great time. (more)"

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12. Erin

Home full-time, fenced in yard!

Annapolis, MD, 21409

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

About: Leaving your fur baby can be scary! (I know from being a crazy dog mom myself). The most important thing when your away is that your pet feels safe... (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. 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)"

Confirmed availability
Christmas and New Year
15. Danielle

It's a Doggy Dog world out there!

Annapolis, MD, 21409

Dog Boarding, Doggy Day Care, Dog Walking

About: Hi! I’m Danielle, an equestrian and canine massage therapist. I love animals and I’m super excited to meet your furry kiddos to play and take care ... (more)

Confirmed availability
Christmas and New Year
16. Sarah

Home full-time Friendly Mom

Arnold, MD, 21012

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

"Sarah loves dogs and has a sweet dog of her own that she really enjoys spending time training. She’s friendly with my dog, but she doesn’t encourage unwanted... (more)"

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17. Kara

Pups Welcome Aboard!

Annapolis, MD, 21403

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

About: Active, outdoorsy young professionals welcome canine companion for playing outdoors and cuddling on settees. Hi! We are Kara & Rory, and we wou... (more)

18. 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)"

19. 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)

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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.