Pet Sitting & Drop In Visits in Winchester Estates, 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. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Janet was great! She appears to have taken great care of the dogs, and sent pictures at every visit. She even made one extra, last minute stop when our fligh... (more)"

2. 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)"

Confirmed available next weekend (Oct 26 - Oct 29)
3. Caroline

Happy pet , happy life !!!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Caroline was the best sitter for our pets! We had a last min. Trip and so glad we booked her. She not only cared for our dog Chip who is afraid of new people... (more)"

4. 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)"

5. Elizabeth

Living life and loving pets!

Easton, MD, 21601

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Elizabeth did a great job. Koda is old and often he needs to be coaxed out for a walk, as was the case this time. However, Elizabeth managed to get him to go... (more)"

6. Jennifer

I'm a huge dog lover and reliable.

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Everything went great. Jennifer showed up on time and left several pictures each time, which I loved. She exercised my pups and they were happy campers. W... (more)"

7. 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)"

8. Allie

Wagging for walks! Dog lover/owner

Annapolis, MD, 21403

House Sitting, Drop-In Visits, Dog Walking

"Allie is the best! She is a responsible, caring person. She has watched my dog many times and I would not hesitate to hire her again. (more)"

9. Rachael

Your dog's home away from home!

Easton, MD, 21601

House Sitting, Drop-In Visits, Dog Walking

About: Being a dog sitter is something that I take very seriously. I know my dog is a part of my family, so I can promise to treat your dog with the same... (more)

10. Rachel

Professional Experience with AWL

Grasonville, MD, 21638

House Sitting, Drop-In Visits

"if you're looking for someone to love and watch over your pets while you're away, it's definitely Rachel! She has a HUGE heart for animals. She has taken gr... (more)"

11. Linda

Exceptional, loving pet care

Easton, MD, 21601

House Sitting, Drop-In Visits, Dog Walking

"Linda has taken care of my jack russell terrier on two different occasions. I came home to find a happy dog and well tended house. I highly recommend! (more)"

12. Catherine

I love animals, especially dogs!!

St Michaels, MD, 21663

House Sitting, Drop-In Visits, Dog Walking

"Catherine has taken care of our dogs on multiple occasions. Because they are so precious to us, we did not want to leave them in a kennel. We wanted to make... (more)"

13. Sophia

Experienced care, Flexible Schedule

St. Michaels, MD, 21663

House Sitting, Drop-In Visits, Dog Walking

About: I have a flexible schedule. I don't have any dogs of my own at the moment but i'm more than happy to spend as much time as possible with your furry... (more)

14. Justine

Walk, Fetch, Groom, Relax

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Justine was great. Did exactly what I ask, showed up when promised and was great with my dog. Would highly recommend her! Brian H Stevensville MD (more)"

15. Callie

Live, Love, Bark!

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

"Usually I am skeptical about leaving Sasha, my two year old husky with a sitter due to her separation anxiety(on top of her off-the-chain energy levels) but ... (more)"

16. Elizabeth

Home most of the time-loves any dog

Easton, MD, 21601

House Sitting, Drop-In Visits, Dog Walking

About: I will treat your dog as if they were mine. At home I have a Bloodhound. I have grown up with a German Shepard and Yellow Labrador. I have experien... (more)

17. Jesse

Dog Lover Sits in YOUR Home

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"I have known Jesse since he was a teen. He has always been a very caring, gentle guy especially when it comes to animals. His family has had dogs for years... (more)"

18. Kara Grace

Experienced vet assistant

Annapolis, MD, 21409

Drop-In Visits, Dog Walking

About: I have owned animals since I was a young child and got my first dog at 8. Since I have adopted 3 more. My father works for Montgomery county Humane... (more)

19. Rozzie

Responsible & Caring Pet Service ?

Annapolis, MD, 21409

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I am a professional Pet Sitter and I will take care of your pets as if they were my own...I am very flexible and will do everything possible to mee... (more)

20. Ashley

I am available to watch your pups!

Grasonville, MD, 21638

Drop-In Visits, Doggy Day Care, Dog Walking

"I would recommend Ashley without hesitation when it comes to being responsible and loving dog caregiver. You will definitely be able to relax and not stress... (more)"

Experience exceptional service and a personalized match

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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 Winchester Estates 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 Winchester Estates, 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 Winchester Estates pet sitters and avoid the kennel.