The #1 network of pet sitters & walkers
200,000+ Sitters
1M+ Reviews
95% Perfect 5-star ratings
18M+ Photo Updates

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.

1. Angelene

Oodles Of Poodles Doggy Sleep Over

Edgewood, MD, 21040

Dog Boarding, Doggy Day Care

"Dimon has weekly daycare with Angelene. This was his first overnight stay. I must say that Angelene by far is the best doggy day care center that any person ... (more)"

Confirmed 4th of July Availability
2. Michelle

Beautiful back yard for your dogs!

Annapolis, MD, 21409

Dog Boarding, Doggy Day Care

"Walks dogs daily. Volunteers at the local SPCA. Has kept rescued dogs, while transitioning out of the shelter to be available for adoption. Volunteers and... (more)"

3. Amanda

Professional Dog Services

Edgemere, MD, 21222

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

About: My name is Amanda and I am insured and certified and trained to watch pets! I also have gained much experience from working at Wag! Walking. I have... (more)

Confirmed 4th of July Availability
4. Jennifer

Home full-time, great neighborhood!

Chestertown, MD, 21620

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

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)

Confirmed 4th of July Availability
5. Elizabeth

Furever friends!

Aberdeen, MD, 21001

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

"Elizabeth was amazing! She took in my 4 month old puppy on short notice for the entire day, and he didn’t want to leave her house by the end of the day. Her ... (more)"

6. Jennifet

Fenced yard,gated neighborhood,

FL, FL, 33543

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

"My dog loved Jennifer. Each time she comes over Aspen runs around in circles until she gets inside. They have a lot of fun together, and I also feel that Asp... (more)"

7. 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)"

8. 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)"

9. 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)"

10. 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)

11. Devin

Will care for dog as if it's my own

Abingdon, MD, 21009

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

"Devin was Nanny to our 10 year old son and our 4 year old Goldendoodle for an entire summer. She took excellent care of Wyatt and Izzy. I'm not sure who lo... (more)"

12. Evalyn

I will assist in dog training!

Sparrows point, MD, 21219

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

"Evalyn has cared for my four cats and two dogs for the last few years. She spends time with them, playing and loving on them and they took to her immediatel... (more)"

Confirmed 4th of July Availability
13. Michelle

Dog owner/dog lover.

Abingdon, MD, 21009

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

"My dogs all love Michelle, and are beyond excited every time she walks up the sidewalk to the house. Whether playing with them, cuddling with them, or going ... (more)"

14. 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)"

Confirmed 4th of July Availability
15. Karoline

Your "go to" when you need it

Greensboro, MD, 21639

Drop-In Visits, Doggy Day Care, Dog Walking

About: I'm a stay at home wife who wants to be your "go to" when you need it. Although new to Rover, I'm not new to dogs and trying to understand them.... (more)

16. 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)"

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)

Confirmed 4th of July Availability
18. Siara

Home full-time, boarding offered!

Middle River, MD, 21220

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

About: I grew up around dogs and I'm comfortable with all sizes and breeds, working dog or lap dog, I can fit your dog's needs! I'm only available in the ... (more)

19. Ashley

Overnight doggie care

Edgwood, MD, 21040

Dog Boarding, Doggy Day Care

"I forgot in my pervious testimonial to include that Ashley watched our dogs for short hours to upwards of 12 hours; sometimes into the wee hours of the morni... (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.