Doggy Day Care in Windward Cove, 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. 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)

3. Jack

Large Fenced Yard + Home Full-Time!

Arnold, MD, 21012

Dog Boarding, Doggy Day Care, Dog Walking

19 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)"

4. Stephanie

We luvs dogs too!

OXFORD, MD, 21654

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

"Meeting Stephanie for the first time was great. We are new to the area and she welcomed us to Oxford. Stephanie made our dog Bella feel comfortable to her h... (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 Holiday Availability
7. Maegan

Dog lover! Home full time - fence

Annapolis, MD, 21401

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

3 repeat clients

"Maegan is one of the most kind-hearted people I know. Animals have always shown through as a soft spot as she loves her dog, Cookie, more than anything imagi... (more)"

8. 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)"

9. 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
10. 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
11. 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)"

12. 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)"

13. 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)"

Available this weekend
14. 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)"

15. Kelly

Training in dog on dog play behavio

Deale, MD, 20751

Doggy Day Care

"Kelly has always loved animals. She had many pets while she was growing up and I don't think there was a time in her life that there wasn't at least one dog ... (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)"

Confirmed Holiday Availability
17. 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)"

18. 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)

19. Rebecca

Home full time - large fenced yard!

Deale, MD, 20751

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

1 repeat client

"Rebecca loved my Golden Retriever, Cyrus, as her own when she would visit or care for him. She provided plenty of TLC and affection in addition to taking hi... (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)


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 Windward Cove 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.