Doggy Day Care in Chestertown, MD

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

Confirmed Memorial day Availability
1. Angelene

Oodles Of Poodles Doggy Sleep Over

Edgewood, MD, 21040

Dog Boarding, Doggy Day Care

101 repeat clients

"Angelene did an awesome job with my Lycos!! He had a great time at her house for doggie daycare!! Thanks again Angelene for taking such good care of my fur... (more)"

Confirmed Memorial day Availability
2. Pearl

I am home during the day or night.

Havre De Grace, MD, 21078

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

2 repeat clients

"I would highly recommend Pearl for all your dogsitting needs. She is a great dog mom and would be an excellent choice for you and your pups while you're out ... (more)"

3. Jennifer

Home full-time, great neighborhood!

Chestertown, MD, 21620

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

1 repeat client

About: I am a 31 year old stay at home mom with two miniature dachshunds. We also have a cat and guinea pigs (the piggies are caged). They are super sweet... (more)

4. Vince

Available 24/7 for scheduling

Baltimore, MD, 21222

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

About: Hi! I'm Vince, I'm 22 years old & I've been helping my mom do part-time dog boarding for almost a year now. She works her main job from 4-10 on wee... (more)

5. 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)"

6. Jennifet

Fenced yard,gated neighborhood,

FL, FL, 33543

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

"Jennifer was an excellent caregiver for my dog. He was always excited to see her, and was well taken care of each time. She always showed up on time, and alw... (more)"

7. Ashby

I'll love yours like I love mine!

Aberdeen, MD, 21001

Dog Boarding, Drop-In Visits, Doggy Day Care

"We have been so happy with the dog sitting services from Ashby. Not only has she watched our sister and brother Havanese Piper and Tucker, she is also the b... (more)"

8. Georgia

Dog-Sitter full-time w fenced yard

Baltimore, MD, 21219

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

"Georgia is a very kind young lady. She loves animals, all kinds of animals actually. She is a very responsible person and I would trust her and have trusted ... (more)"

9. Brittany

I love dogs, hikes, cats, and bikes

Joppa, MD, 21085

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

"Brittany is one of the most caring human individuals I have ever met, particularly when it comes to her care for animals. Two of the most prominent members o... (more)"

10. Terry

We Love Pets!

Pasadena, MD, 21122

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

14 repeat clients

About: We have been pet lovers all of our lives. Growing up we had dogs, cats, snakes, chameleons, birds, rabbits, a duck, fish, hamsters...and the list ... (more)

11. Rich

Large fenced yard/run space

Joppa, MD, 21085

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

"Rich has been a wonderful friend of mine for a long time. He has been around my dogs and they absolutely ADORE him. I almost think they love him more than me... (more)"

12. Kevin

Dog groomer/ boarder/trainer UK

edgewood, MD, 21040

Dog Boarding, Doggy Day Care

"Kevin and Julie looked after my did Reggie, a cocker spaniel, while my husband and I were on holiday. They took excellent care of him . Gave him correct diet... (more)"

13. 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)

14. Carla

Sensitive, Smart, Veteran

Dundalk, MD, 21222

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

13 repeat clients

"She was very friendly and nice. Sent me pictures of my dog having fun and on walks. I would recommend her to everyone. The best dog eitt ever I've had so far... (more)"

Confirmed Memorial day Availability
15. Elizabeth

Furever friends!

Aberdeen, MD, 21001

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

10 repeat clients

"Shelby was so happy when I picked her up at the end of the day! I will definitely turn to Elizabeth if I need puppy daycare again. (more)"

16. 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)"

17. Danielle

Dog loving individual

dundalk, MD, 21222

Drop-In Visits, Doggy Day Care, Dog Walking

About: I am pretty flexible for the summer. Always willing to help out as needed. I have a dog of my own and understand what it's like to need care for ... (more)

18. Ashley

Overnight doggie care

Edgwood, MD, 21040

Dog Boarding, Doggy Day Care

"Ashley was our dog sitter for our Bovier Vinca. Vinca loved Ashley and always was so excited to see Ashley each and every time. Ashley was dedicated to wha... (more)"

19. Aaliyah

I love animals so much!

Essex, MD, 21221

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

"I have to say that Aaliyah is a wonderful person to have watch your dogs. She is loving, caring, and willing to always have fun. Treats are a thing she loves... (more)"

20. Ken

I actually play with the dogs!

Middle River, MD, 21220

Drop-In Visits, Doggy Day Care, Dog Walking

About: For offsite visits, I'm on time and play with the dogs. If using day care, I live off the main road and have a large privacy fenced back yard that ... (more)


We've been there, cancelling meetings or plans with friends to make sure you can be there for your dog. Good news: You can easily find and book doggy day care in Chestertown on Rover. Whether you need a one-time daytime pet sitter or someone to take care of your beloved pet every weekday, we've got you covered. Care for your dog and peace of mind for you are just a few clicks away. If you already have a favorite overnight sitter, ask them if they offer day care too. Or, if you've never used Rover, this is the perfect opportunity to find a new best friend for your dog when you're at work. We can help you find a sitter who'd love to watch your dog.