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.

1. Bram

Your dog's home away from home

Annapolis, MD, 21403

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

5 repeat clients

"We're so grateful that Bram was able to accommodate our last minute daycare request. A kind and attentive sitter, a beautiful home, and a sweet and playful ... (more)"

Confirmed Holiday Availability
2. Alexandra

loving, nurturing pet sitter

pasadena, MD, 21060

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

12 repeat clients

"I have been to many dog sitters with my new pup and she has NEVER been so happy than she was with Alexandra! Alexandra exercised her, played, and allowed sup... (more)"

Confirmed Holiday Availability
3. Doug

South County R&D

West River, MD, 20778

Dog Boarding, Doggy Day Care

5 repeat clients

About: Rebecca & Doug are a mature pet-loving couple. We live in a neighborhood filled with other dogs and safe for walking, and have a two-level house wh... (more)

4. Jack

Large Fenced Yard + Home Full-Time!

Arnold, MD, 21012

Dog Boarding, Doggy Day Care, Dog Walking

20 repeat clients

"Jack and his family were amazing! We were very nervous being away from our puppy the first day, but Jack lessened our fears by sending us frequent photos and... (more)"

Confirmed Holiday Availability
5. Tiffany + Megan

Dogs,Cats,Birds,Horses Any Animal❤️

Riva, MD, 21140

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

7 repeat clients

"Kara had a wonderful daycare session with Tiffany and Megan. Both kept constant supervision of her and their well-behaved dogs. Yes! Their dogs are in on the... (more)"

6. Neal

Dog love to run/hike? Perfect!

Stevensville, MD, 21666

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

1 repeat client

"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)"

Confirmed Christmas Availability
7. Chelsea

Experienced/Caring/Reliable!

Davidsonville, MD, 21035

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

1 repeat client

"If you are looking for the BEST combination of physical activity, adventure, love and incredible care for you fur baby while you are away for a few hours or ... (more)"

Confirmed Holiday Availability
8. Maegan

Dog lover! Experienced care

Annapolis, MD, 21401

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

3 repeat clients

"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)"

9. Sharon

Caring, Professional Dog Lover!

Edgewater, MD, 21037

Dog Boarding, Doggy Day Care

6 repeat clients

"Awesome!!!! She's amazing. So glad I found her. (more)"

10. Nash

Certified Service Dog Trainer

Annapolis, MD, 21403

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

"Nash is an incredibly dedicated young man and within all aspects of life, academics, family, and his community. Beyond dedicated he also exhibits a great pas... (more)"

Confirmed Holiday Availability
11. Kelcie

Farm lovin and livin!

West River, MD, 20778

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

"Kelcie is truly a lover of all things animal! Honestly, no one else I would trust taking care of my dogs other than her. She treats them how you would hope e... (more)"

Confirmed Holiday Availability
12. Norah

Energetic and ready for your dogs

Stevensville, MD, 21666

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

1 repeat client

"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)"

13. Ashley

Experience animal caretaker

Annapolis, MD, 21403

Dog Boarding, 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)"

14. Jess

Home full-time fenced in yard

Annapolis, MD, 21404

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

"Jess is an amazing pet sitter, and our dog Mo absolutely adores her. We have relied on Jess to watch our dog over the past 7 years, and she has become like ... (more)"

15. Lauren

Fur baby lover

Annapolis, MD, 21401

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

2 repeat clients

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

Confirmed Holiday Availability
16. Penny

Dogs make me happy :)

Annapolis, MD, 21403

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

"Penny would make an excellent pet sitter. Since birth, she has grown up with many different kinds of animals and had the responsibility of taking care of the... (more)"

17. Kimberly

Pets can play while you're away!

Pasadena , MD, 21122

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

"I would highly recommend Kimberly to care for your pet. She is very responsible and treated our dog with loving care and provides a safe environment. Thank... (more)"

Confirmed Holiday Availability
18. Sydney

Owner and Lover of dogs

Annapolis, MD, 21403

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

1 repeat client

"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)"

19. Greg

Dog Heaven in Downtown Easton

Easton, MD, 21601

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

About: If your dogs think they are people, they will fit right in at our place. Your dog will love visiting our little urban homestead. We have a fully ... (more)

Confirmed Holiday Availability
20. Imani

I've won a few four legged races

Shady side, MD, 20764

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

About: I think the most important thing about providing amazing service is loving what you do, And I absolutely love caring for our four-legged buds! I ha... (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.