Pet Sitting & Drop In Visits in Oakwood, MD

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

1. Victoria

Experienced & Caring Pet Sitter!

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

41 repeat clients

"Fantastic!! (more)"

2. Kate

Must love dogs...Yes, that's me!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Katie rocks. Quick to respond. Takes care of business. Very friendly. Recommend ???? (more)"

Confirmed New Years Availability
3. Allie

Wagging for walks! Dog lover/owner

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"Allie was amazing! She took detailed pictures and kept me in the loop with everything going on with my pup. Will definitely contact her in the future!! :) (more)"

Confirmed Holiday Availability
4. 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)"

Confirmed Holiday Availability
5. Karlee

Always up and ready!

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Karlee was an absolute amazing dog sitter for Charley. I asked her to come three times a day to feed him, take him out and take him for walks and she did it ... (more)"

6. Bram

Your dog's home away from home

Annapolis, MD, 21403

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

5 repeat clients

"Great! Bram will definitely be top on our list when we need a sitter! (more)"

7. Kirsten

I'll run/hike/SUP with your pup!

Annapolis, MD, 21401

House Sitting, Drop-In Visits, Dog Walking

"Kirsten has taken care of my dogs Bandit and Buster for years. They just love her and she has become part of the family. I never worry about them when they a... (more)"

8. Lauren

Attentive, Reliable and Fun!

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

"Lauren was great! She came when she said she would, and sent pictures of her playing with my cats. I'll definitely contact her again if I need someone to loo... (more)"

Confirmed Christmas Availability
9. Nicole

I love anything to do with dogs!

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Nicole is super great with animals and she loves them a lot. I've known her since high school and I know she's responsible and trustworthy, especially when i... (more)"

Confirmed Holiday Availability
10. 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)"

11. Kelli

Home full time, large fenced yard

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

1 repeat client

"Kelli took great care of Boomer with two drop-in visits. Boomer is only 13 weeks, so schedule and details are key in getting her house trained. Kelli kindly... (more)"

12. Brittney

Leave your dog with a loving couple

Annapolis, MD, 21403

Dog Boarding, Drop-In Visits

About: Hi! My husband and I live in Hillsmere Shores down by the water and have a huge fenced in back yard. We currently have a 5 year old chocolate lab ... (more)

13. 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)"

14. Molly

Run ´n play outside, the best side!

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Molly has a kindred spirit to all species. Dogs, cats, horses, rabbits (that I’ve personally witnessed) are instinctively drawn to her good and gentle soul... (more)"

15. Jamie

Homemaker, excuse to get out! :)

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"Your fur babies will thank you for having Jamie care for them! Jamie is responsible, dependable and trustworthy. She will treat your pets well and her calmin... (more)"

16. sonya

Pet sitting by Sonya

Edgewater, MD, 21037

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sonya was so great! She came over to meet Reese to make sure that he was comfortable with her! She sent pictures and gave me a detailed message about taking ... (more)"

Confirmed Holiday Availability
17. Rebecca

I love being a caretaker for dogs.

annapolis, MD, 21403

Drop-In Visits, Dog Walking

1 repeat client

"Rebecca has always loved dogs. She is the one who wanted to adopt rescue animals....which we have done for all of our dogs. She takes care of Peaches an... (more)"

18. Maddy

Your dogs home away from home!!

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

"Maddy is awesome! she loves my dog and my dog loves her. One of the few people I can let my dog go out of sight with and not be worried . When Ellie(my dog) ... (more)"

Confirmed Holiday Availability
19. Maria

Satisfaction Guaranteed Home & Pet

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Maria Really knows how to handle dogs. Normally my 90lb black lab takes me for a walk. But when Maria stops by for his afternoon walks, he is on his best beh... (more)"

20. Becca

Experience caring for all animals!

Annapolis, MD, 21403

Drop-In Visits, Dog Walking

1 repeat client

"Becca is one of the bests, if not the best sitter we have ever had! She is wonderful with our dog Felix. One week of working with her was a real breeze. She ... (more)"


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Oakwood pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Oakwood, MD, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Oakwood pet sitters and avoid the kennel.