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.

Confirmed Holiday Availability
1. Madison

Friendly petsitter

Havre de grace, MD, 21078

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"She is so great with dogs. my three pit bulls loved her when she came in my house for first time 7 years ago. (Normally, my family pit bulls don't like stran... (more)"

Confirmed Holiday Availability
2. Jocelynn

Avid animal lover and Zookeeper =)

Colora, MD, 21917

House Sitting, Drop-In Visits, Dog Walking

"Jocelynn was great, very detailed in her reports and on time. Jocelynn was reliable and we had no issues during the week we used her for drop in visits. (more)"

3. Kimberly

Former Supervisor Boarding Facility

Darlington, MD, 21034

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)"

4. 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)

Confirmed Holiday Availability
5. 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)"

Available this weekend
6. 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)"

Confirmed Holiday Availability
7. Christyne

People Person and Dog Lover!

North East, MD, 21901

House Sitting, Drop-In Visits, Dog Walking

"Christyne spends quality time with your pet, playing fetch, long walks, giving treats and the all time favorite belly rubs. If your pet does well with bath t... (more)"

8. Maurice

Current dog owner

Nottingham, PA, 19362

Drop-In Visits

"I can think of no better dog-sitter than Maurice! He is responsible, follows your instructions to the letter, lavishes your pets with attention, understands ... (more)"

9. 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)

Available this weekend
10. 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)"

11. 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)

Available this weekend
12. Jess

Responsible, reliable, punctual, pl

Oxford, PA, 19363

House Sitting, Drop-In Visits, Dog Walking

"More than took care of my dog, who loved her. She washed his dog bowl and cleaned my floor from muddy dog prints when coming back in from playing. Very respo... (more)"

13. Megan

Home full-time in dog-friendly area

Darlington, MD, 21034

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

About: I love dogs of all kinds and have been caring for them since I was a kid. My boyfriend and I both take care of the dogs we sit, including feeding, ... (more)

14. 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)"

15. Miranda

Miranda's Happy Pup's

Elkton, MD, 21921

Drop-In Visits, Doggy Day Care, Dog Walking

About: I am Miranda, I have a great deal of experience with animals especially dogs and horses! They are my passion and they will definitely play a big pa... (more)

Confirmed Holiday Availability
16. Mackenzie

Every animal has his or her story

havre de grace, MD, 21078

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

3 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)"

17. Brittani

I am responsible and trustworthy.

Havre de grace, MD, 21001

House Sitting, Drop-In Visits, Dog Walking

About: I have grown up with dogs. I currently do not have a dog but i do have a kid and a cat...so its almost the same as having 2 pets :)One of my fondes... (more)

18. Talena

Dependable, Honest, Trustworthy

Oxford, PA, 19363

House Sitting, Drop-In Visits, Dog Walking

"Talena has done a wonderful job taking care of our two dogs and one cat. One of our dogs is very shy and Talena kept working with her until Rosie was no long... (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. Donna

I am mom to all!

North East, MD, 21901

Drop-In Visits, Doggy Day Care, Dog Walking

About: I love animals. At one time we had 9 dogs, 3 cats, 2 hamsters, a turtle and fish. Animals are family. They follow me like I am mom. I could never ... (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.