Pet Sitting & Drop In Visits in Oakland, 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. Travis

Experienced Dog/House Sitter

Cumberland, MD, 21502

House Sitting, Drop-In Visits, Dog Walking

"Travis stayed with our 3 dogs during the week of this most recent Thanksgiving. He was very conscientious and took excellent care of our dogs. The dogs see... (more)"

2. Deborah

Love me ... love my dog!

Oakland, MD, 21550

House Sitting, Drop-In Visits, Dog Walking

"Deb has a wonderful heart for any animal. Her special love is dogs, and whenever she see one, a special point is made to speak to the owner and give love and... (more)"

3. Deborah

Love me ... love my dog!

Oakland, MD, 21550

House Sitting, Drop-In Visits, Dog Walking

"I couldn't think of an easier thing to do than give Deb an enthusiastic thumbs-up in regard to her love of all animals and in particular the four-legged dogg... (more)"

4. Travis

Experienced Dog/House Sitter

Cumberland, MD, 21502

House Sitting, Drop-In Visits, Dog Walking

"Travis stayed with our 3 dogs during the week of this most recent Thanksgiving. He was very conscientious and took excellent care of our dogs. The dogs see... (more)"

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Learn About Premier

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 Oakland 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 Oakland, 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 Oakland pet sitters and avoid the kennel.