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. Caroline

Happy pet , happy life !!!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Caroline is awesome! She always seems very in tune with Sully and what he wants and needs. She gives detailed feedback about their time together and that mak... (more)"

Confirmed Memorial day Availability
2. Janet

Home full-time fenced yard and pool

Chester, MD, 21619

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

9 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)"

3. Casey

certified veterinary assistant

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Casey is amazing - not only will she love your dogs when walking or puppy sitting but she also let's them go swimming in her puppy pool! My puppies love her ... (more)"

4. Jennifet

Fenced yard,gated neighborhood,

FL, FL, 33543

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

"My dog loved Jennifer. Each time she comes over Aspen runs around in circles until she gets inside. They have a lot of fun together, and I also feel that Asp... (more)"

5. Nicole

My dogs are my life!

Stevensville, MD, 21666

Dog Boarding, Drop-In Visits, Dog Walking

About: I am a hard working mother who has a love for animals. I have a great personality and I am very easy to get along with. I have two of my own dogs w... (more)

6. Audreanna

Home full time, fenced in yard

Centreville, MD, 21617

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

About: I am basically a stay at home mom. I work one day a week at a dog grooming salon, I am a pet stylist! I have always loved working with dogs and I s... (more)

7. Jenna

Home full-time and loves to play!

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

About: I am currently employed as an elementary school substitute teacher and work part-time at the front desk of a yoga studio. At the moment my schedule... (more)

8. Valerie

Animal Lover Ready to Play Fetch!

Easton, MD, 21601

House Sitting, Drop-In Visits, Dog Walking

"Let me start this off by saying: Valerie is a great pet sitter! I have a very temperamental pet hedgehog that she spent a lot of attention on trying to win o... (more)"

9. Bri

Treat your dogs to a Staycation

easton md, MD, 21601

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

"Bri is a great caretaker for your animals. She has a lot of experience with dogs, cats, and other small animals. She cares a lot for the animals in her life. (more)"

10. Victoria

Looking to love on all the animals!

Annapolis, MD, 21409

Dog Boarding, Drop-In Visits, Dog Walking

About: I love dogs and have been around them since I was little. The only reason I don't currently have a dog is because I don't have the funds available ... (more)

11. Callie

Live, Love, Bark!

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

12. 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

"I've worked with Neal the last few years and found him to be a hard and open worker. He will ensure the safety and comfort of your pets and ask questions whe... (more)"

Confirmed Memorial day Availability
13. Nick

I love dogs!

Easton, MD, 21601

House Sitting, Drop-In Visits, Dog Walking

About: I have been dog sitting for about a year and a half for family friends and have really enjoyed it. I am available upon request and am willing to wo... (more)

14. 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

"NorH took care of my pugs without any problems. We are happy to have found her and appreciate her last minute help to have carefor the pups. (more)"

15. Kelli

Dog lover! Home full-time

Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Kelli is the best doggy care giver I could ever hope for!! Starting from when my pup, Mulligan, was a young puppy, Kelli has taken care of him. She always co... (more)"

16. Kathleen

Your dog's safety is my priority!

Stevensville, MD, 21666

Drop-In Visits, Dog Walking

"Kathleen has been a trusted and responsible employee of Animal Resource Foundation (ARF) since 2010. Over the years Kathy has proved to be dependable and he... (more)"

17. Rachel

Professional Experience with AWL

Stevensville, MD, 21666

House Sitting, Drop-In Visits

"I have known Rachel for her whole life. She is very sweet, honest and reliable. She loves animals like no-one I know. She would be a great asset to have work... (more)"

18. Linda

Exceptional, loving pet care

Easton, MD, 21601

House Sitting, Drop-In Visits, Dog Walking

"We hired Linda to pet/house sit our dog Zeus. Zeus really seemed to love Linda's company very much and it was such peace of mind knowing he wasn't crated up ... (more)"

19. Samantha

Flexible schedule and active!

stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Samantha is great! She is responsible, dependable and caring. She clearly loves animals and enjoys what she does. Our two dogs are always very excited to see... (more)"

20. Jena

Experienced Pet Sitter 4+ Years

Grasonville, MD, 21638

Drop-In Visits, Dog Walking

About: My name is Jena, not only have I had pets of my own since I was little, but I have also owned a pet and house sitting business for the past 4 years... (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 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.