House Sitting in Chester

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.
Calendar Recently Updated
1. Jason Verified Enhanced Background CheckRover 101

Reliable & Responsible, Dog Lover!

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Jason and Chloe were a great match! Chloe can be a little hard to handle but Jason did great with her. I know she was well taken care of and loved on while w... (more)"

Confirmed availability
This weekend
2. Bohdanna Verified Background CheckRover 101

I Love Furbabies!

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"This is the fourth time we have booked Bo and she is a wonderful sitter. She sends great updates with pictures and stories about your pet. She is careful to ... (more)"

3. Madison Verified Background Check

Responsible and flexible

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Maddie made leaving my dog home easy while we went away for a long weekend. He was calm and happy! (more)"

4. Eric Verified Enhanced Background Check

Been dog sitting since I was 12

Annapolis, MD, 21409

House Sitting

"Eric was amazing! He was cery responsive and was able to house / dogsit on short notice. Our Weimaraner is not used to strangers in the house but warmed up t... (more)"

Calendar Recently Updated
5. Meghan Verified Background Check

My dog is Family and so is Yours!!!

Chester, MD, 21619

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

"My name is Diane Miller and Meghan has been dog sitting for me for over a year now. When I am away on business or vacation I do not worry at all about Duke.... (more)"

Calendar Recently Updated
6. Hannah Verified Background Check

Relaxed home, Frequent exercise

Annapolis, MD, 21409

House Sitting, Drop-In Visits

"I’ve known Hannah for about 5 years now. She loves animals so much. They bring her so much joy and she truly has a passion for taking care of them and provid... (more)"

Calendar Recently Updated
7. Ashley Verified Background CheckRover 101

Pet Care When You're Not There!

Annapolis, MD, 21409

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

"Ashley took great care of our yellow lab while we were away for the weekend. She stayed at our house and made sure he got lots of attention and walks--also s... (more)"

Calendar Recently Updated
8. Breanna Verified Background Check

I know where all of good parks are

chester, MD, 21619

House Sitting, Drop-In Visits, Dog Walking

"Breanna is a very dependable,respectful and responsible young adult. She will treat you fur baby like it is her own. She loves all animals equally (more)"

Confirmed availability
This weekend
9. Ty Verified Background Check

Your Dog’s Best Friend

Annapolis, MD, 21409

House Sitting, Dog Walking

"Ty did a great job watching our dog. I would definitely recommend her to others. (more)"

Calendar Recently Updated
10. Erica Verified Background Check

Experienced animal caretaker

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Erica has an amazing gift with animals. If you are looking for someone to love your dog as much as you, Erica is an exceptional choice. We always have Erica... (more)"

Calendar Recently Updated
11. Lucy Verified Background Check

Loving and Experienced

Annapolis, MD, 21409

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

About: Was a rescue mom for over 7 years, trained by the Fairfax County Animal Shelter. Love animals of all types and experienced in kittens, puppies, dog... (more)

12. Emily Verified Background Check

Play, walk, run...

Chester, MD, 21619

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

"Emily was so wonderful with my Beaux. He’s a miniature dachshund puppy and can be a handful sometimes. Beaux had a great time with her and her boys and came ... (more)"

Confirmed availability
This weekend
13. Jessica Verified Background Check

Dog lover all the way

Grasonville, MD, 21638

House Sitting, Drop-In Visits, Dog Walking

About: Hi I’m Jess, I have two dogs of my own one a small Jack Russell mix with Chihuahua, and a lab. I volunteer at my local shelter all the time, walki... (more)

Confirmed availability
Thanksgiving
14. Paige Verified Enhanced Background Check

Experienced and Friendly Caretaker

Queenstown, MD, 21658

House Sitting, Drop-In Visits, Dog Walking

"Paige did a great job sitting for our Welshie for a week. She was very helpful with other tasks around the house and our dog was a very happy pup while we w... (more)"

15. Lindsey & Rocco Verified Background Check

DOG HEAVEN! large fenced yard!

Queenstown, MD, 21658

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

"I have observed Lindsey caring for dogs and cats for many years and know her to be responsible, caring and trustworthy. She currently owns a pure bred golde... (more)"

16. Stephanie Verified Background Check

Love all dogs and breeds

Annapolis, MD, 21409

House Sitting, Drop-In Visits, Dog Walking

"Stephanie came and met my 2 dogs and 2 cats and spent time and asked questions so she was sure to know exactly what to do. My one dog has anxiety and can ac... (more)"

Confirmed availability
This weekend
17. Joanne Verified Background Check

Home to all fur beings!

Grasonville, MD, 21638

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

About: Hi I’m Jo, many of my fur butts call me Auntie Jo. I work a split shift so even during the week I am in and out, never leaving your baby for too lo... (more)

Calendar Recently Updated
18. Rachel Verified Background Check

Experience in Veterinary Assistance

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"Rachael did a great job taking care of our two dogs for a week in our home. She sent me some pictures and contacted me when she had a question. She is very s... (more)"

19. Kimberly Verified Background Check

Your pets will be in GREAT hands

Stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

"I worked with Kim several years ago in a veterinary hospital/kennel. She was always attentive to every pets needs and was very kind and loving to all our gu... (more)"

20. Annie Verified Background Check

Pet Lover of all kinds!!!!

stevensville, MD, 21666

House Sitting, Drop-In Visits, Dog Walking

About: I LOVE all animals! I am very passionate about animals and the care that they receive. I have been working with a shelter for over 10 years and hav... (more)


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Chester house sitting needs. On Rover, it's easy to find a loving dog sitter in Chester who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Chester house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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 dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Chester for your dog — people who'll treat him like family.