Pet Sitting & Drop In Visits in Winchester Village, 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. Lorel

Flexible, reliable dog lover

Aberdeen, MD, 21001

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

1 repeat client

"Lorel was very kind and gentle with Gracie. It takes awhile for Gracie to warm up to people but by the time Lorel left...they were friends. Scheduled another... (more)"

2. Theresa

Treat your dog with LOVE.

Havre de Grace, MD, 21078

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

8 repeat clients

"Theresa took great care of my pups and made sure they were loved the way I would love them. <3 I will definitely ask her back when I need a caregiver for m... (more)"

3. Michael

Tall, strong, dog-walker.

North East, MD, 21920

Drop-In Visits, Dog Walking

"Michael has taken great care of my dog. I have used him as a pet sitter and also just to take him out for walks when I’m unable to get home during the day. ... (more)"

4. Madison

Friendly petsitter

Havre de grace, MD, 21078

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Madison and Chris are FANTASTIC! We adore our kitties, and would rather stay home unless we found the perfect sitters! Lucky for us we did! They treated ou... (more)"

5. Pearl

I am home during the day or night.

Havre De Grace, MD, 21078

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

1 repeat client

"I would highly recommend Pearl for all your dogsitting needs. She is a great dog mom and would be an excellent choice for you and your pups while you're out ... (more)"

6. Kimberly

Former Supervisor Boarding Facility

Darlington, MD, 21034

Dog Boarding, Drop-In Visits, Dog Walking

8 repeat clients

"Kim has watched Bindi for us multiple times! And she's always excited to return to Kim's, sometimes I don't think she misses me at all! (more)"

7. Shay

Will care for your dog like my own

Havre De Grace, MD, 21078

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

"At the end of Summer, my wife and I took a trip out of the country and we were looking for someone reliable to house sit our Great Dane, Sparky, Shay came re... (more)"

8. Christyne

People Person and Dog Lover!

North East, MD, 21901

House Sitting, Drop-In Visits, Dog Walking

"Christyne is a wonderful pet sitter. She loves all animals and they love her in return. She is detail oriented and follows the owner's wishes to the letter. ... (more)"

9. Mackenzie

Every animal has his or her story

havre de grace, MD, 21078

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

5 repeat clients

"Mackenzie is responsible, trustworthy, and caring in all aspects of life and especially when it comes to four legged friends. She has worked professionally a... (more)"

10. Taylor

7+ Years of Pet Sitting Experience!

North East, MD, 21901

Dog Boarding, House Sitting, Drop-In Visits

"Taylor was wonderful with our puppy Oliver. She sent us pictures and gave us updates. Will definitely use her again in the future. (more)"

11. Lydia "Lid"

Currently home full time

Port deposit, MD, 21904

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

About: I currently am looking for a job but until then I’d love to take care of dogs. I love all dogs and they love me. I have a very energetic Pomeranian... (more)

12. Natalie

Home full time with fenced yard

North East, MD, 21901

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

"Natalie would make a wonderful asset to your company! I know that she would provide safe, competent, compassionate and loving care to the pets in your servi... (more)"

13. Megan

Very Experienced Pet-sitter

Conowingo, MD, 21918

House Sitting, Drop-In Visits, Dog Walking

About: Hey there! I am a recent college graduate who pet-sat/dog-walked her way through college. I worked around the Towson/Baltimore area for a professio... (more)

14. Mallory

Love dogs & take great care of them

Havre de Grace, MD, 21078

House Sitting, Drop-In Visits, Dog Walking

About: I am very flexible with scheduling. I am pretty much free all day, every day, besides when I am at school on weekdays from 7:00-10:35. I always sho... (more)

15. Jaclyn

Dog & Cat Lover !

Perryville, MD, 21903

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

2 repeat clients

"Jaclyn is a dedicated and trustworthy young lady. She loves animals and we have had her house and dog sit without worrying about a thing. We love her and h... (more)"

16. Dakota

I treat yours like i treat mine!

Rising Sun, MD, 21911

House Sitting, Drop-In Visits, Dog Walking

About: I love puppies and dogs in general! I've had my shitzu poodle mix for 9 years growing up. Ive been through some of the worst messes with him?. I am... (more)

17. Jeb

Flexible Scheduled Dog Companion

Havre de Grace, MD, 21078

House Sitting, Drop-In Visits, Dog Walking

"Jeb has been taking care of my pets (Also, my backup sitter for my clients) for years. As a dog sitter myself I'm very picky about who watches my animals. Es... (more)"

18. Tristan

Dog whisperer ?

Northeast, MD, 21901

House Sitting, Drop-In Visits, Dog Walking

"Tristan really loves the dogs, they listen to him more then my husband and I! He is a realiable young man that gives the dogs/cats good attention they should... (more)"

19. Helen

I am an active, caring dog-lover!

Darlington, MD, 21034

House Sitting, Drop-In Visits, Dog Walking

"Helen is a wonderful person with enthusiasm and a love for dogs! She is outdoors-y and a great companion for any playful pup. Her responsibility and gentle n... (more)"

20. Elizabeth

Pets Play ALL-day Sleep at Night:)

Colora, MD, 21917

Drop-In Visits, Dog Walking

About: I have now 4 years of experience with many different breeds and temperates. I'm working toward a career with animals. I am willing to work with you... (more)


Rover.com is the simple, savvy way to find and book Winchester Village drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Winchester Village. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.