Doggy Day Care in Winchester Estates, 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)"

Available this weekend
2. Alexandra

loving, nurturing pet sitter

pasadena, MD, 21060

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

12 repeat clients

"Very friendly , she treated Rocky like family and I will contact her for future stays. She keeps you update and also she sends pictures of your dog?. I was... (more)"

3. Doug

South County R&D

West River, MD, 20778

Dog Boarding, Doggy Day Care

6 repeat clients

About: We live in a neighborhood filled with other dogs and safe for walking, and have a two-level house where dogs are free to roam and make themselves a... (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)"

5. Stephanie

We luvs dogs too!

OXFORD, MD, 21654

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

"Stephanie was great with my dog--he loved her and had such a good time in her garden, on the beach, and out and about. She was also very warm and flexible, a... (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)"

7. Chelsea

Experienced/Caring/Reliable!

Davidsonville, MD, 21035

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

2 repeat clients

"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)"

Available this weekend
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)"

Available this weekend
9. Megan

Home Full Time - Ready to help

Edgewater, MD, 21037

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

About: I love animals, all animals! I am available to assist you with animal care needs. From dog walks to boarding, just give me a shout! I attend Dog ... (more)

Available this weekend
10. Sarah

Energetic student, excited to meet

Annapolis, MD, 21409

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

"Sarah is very professional, communicative, always on time, and above all, great with my dog. She sent pictures and text messages to keep me "in contact" with... (more)"

11. 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)"

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)"

Confirmed President's Day Availability
13. Kelcie

Farm lovin and livin!

West River, MD, 20778

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

1 repeat client

"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)"

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)"

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)"

16. 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)

Available this weekend
17. 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)"

18. 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)"

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)

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)


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 Winchester Estates 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.