House Sitting in Chestertown

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability
Thanksgiving
1. Ashton Verified Background Check

Certified Animal Lover!

Cecilton, MD, 21913

House Sitting, Drop-In Visits, Dog Walking

"Ashton has groomed our English Springer Spaniel since he was a puppy. He is four years old now and because of the patients and gentleness that Ashton has sho... (more)"

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2. Brooke Verified Background Check

Your New Secret Weapon!

Centreville, MD, 21617

House Sitting, Drop-In Visits, Dog Walking

"I truly thank Brooke for taking care of my Dozy Doo! As many of you can relate, they are our babies! I think he had a good time with her, hiking in Tuckaho... (more)"

Confirmed availability
Thanksgiving
3. Haley Verified Enhanced Background Check

I can sit, walk, and run with pets!

chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Haley did a great job! She was great with both my dogs and sent a bunch of pictures which was awesome! I would definitely recommend! (more)"

4. Madison Verified Background Check

Animal lover

Chestertown, MD, 21620

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

About: I have had dogs, cats, and fish my entire life and I started walking dogs about 7 years ago. I have watched dogs and cats the past three years. I c... (more)

5. Michaela Verified Background Check

I'll run and play with your dog!

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Michaela has taken care of our dog numerous times. This last time she house sat for us for the weekend. She was totally responsive and responsible, doted o... (more)"

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6. Shannon Verified Background Check

Dog Lover ❤️💙💜🧡💛💚

Chestertown, MD, 21620

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

"Shannon is an amazing caregiver. She is a true animal lover and treats animals like they are part of the family. She is very trustworthy and honest. She care... (more)"

7. Stacey Verified Background Check

I love them while you leave them!

Ridgely, MD, 21660

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

About: I have never been without a pet, including cats, dogs, birds and fish. I know the stress of leaving a pet for vacations, work or emergencies. I l... (more)

8. Jacqueline Verified Background Check

Law student and dog lover!

Centreville, MD, 21617

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

"Jacqueline was prompt communicative and took great care of our dog. Will definitely book again! (more)"

9. MEG LIZ Verified Background Check

A dog a day keeps the doctor away.

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

About: Hi everyone! I left the nest a few years ago and I only get to see my family dog every few weeks. I really miss the love and compassion of animals,... (more)

10. Takeyah Verified Background Check

Fun college student & animal lover

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

About: I am a fun college student who loves animals of all types, breeds, and sizes. I have been raising and training animals since I was a young child. B... (more)

11. Cynthia Verified Background Check

No such thing as pets they are fami

Rock Hall, MD, 21661

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

About: I have been born and raised to take care of any type of family member from the small lizard to largest dog to feathered friends and horses. I love ... (more)

12. Aimee Verified Background Check

Let Me Care for Your Pets

Church Hill, MD, 21623

House Sitting, Drop-In Visits, Dog Walking

"Aimee is a wonderful person who I trusted with my son, 3 legged Basset Hound and Boxer mix. She is dependable and kind. She will take good care of your fur... (more)"

13. Natalie Verified Background Check

Loves dogs and cats!

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Natalie has been watching my 9 year old yellow lab for about five years now, every time that we go away on vacation. My dog absolutely loves her! She takes h... (more)"

14. Shannon Verified Enhanced Background Check

Happy Pet - Happy Life

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

"Shannon is very knowledgeable, experienced, responsible, and most of all caring and attentive to our two dogs. Can't express our appreciation in just 25 words. (more)"

15. Mackenzie Verified Background Check

Mackenzie

Millington, MD, 21651

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

About: I’ve always been around animals since I was a little kid especially dogs. I have 2 loving energetic labs who enjoy play dates with other dogs. I’m ... (more)

16. Brianna Verified Background Check

Great foster mom!

Chestertown, MD, 21620

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

About: I've been working in animal shelters for the past year. I started off as an Animal Care Technician, caring for the shelters 80+ cats and dogs daily... (more)

17. Catherine Verified Background Check

Fellow- lover and caretaker of pets

Chestertown, MD, 21620

House Sitting, Drop-In Visits, Dog Walking

About: I have great familiarity with how to care for and love pets of different kind and attitude, as I have owned pets from early childhood to present ad... (more)

18. Danielle Verified Background Check

Animal Loving Sitter

Centreville, MD, 21617

House Sitting, Drop-In Visits, Dog Walking

"I would definitely recommend Danielle to watch my pets. She has watched all 3 of my dogs at once and did a great job. Danielle is a teacher, and a mother so ... (more)"

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19. Tatiana "Tee" Verified Background Check

Your neighborly dog enthusiast

Worton, MD, 21620

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

About: Hi there! Pleasure to meet you, my name is Tatiana and I am a current college student. I love animals and have plenty experience walking and carin... (more)

20. Nicole Verified Background Check

Lots of experience caring for dogs!

Henderson, MD, 21649

House Sitting, Drop-In Visits, Dog Walking

"I highly recommend Nicole! She’s great with my pets and dependable! She’s been taking care of my pets for years now; dogs, cats, ferrets, birds, rats, and ... (more)"


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