House Sitting in Chester

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

Search Results

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Madeline B.
Energetic lover of animalsAnnapolis, MD, 21401
House Sitting, Drop-In Visits, Dog Walking

Madeline was absolutely amazing. She took care of Hendricks like he was her own. Spoiled him, walked and exercised him. He loves her! She took care of our home… (more)

from
$40
per night
Eric R.
2.
Been dog sitting since I was 12Annapolis, 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 to E… (more)

from
$40
per night
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Jamie P.
3.
Best Buddy for the Furry RoyaltyAnnapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking

We are so grateful for the care and attention Jamie gave to our 2 dogs. One of which is senior with special needs. She shared photos every day with updates. Jam… (more)

from
$37
per night
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Chloe E.
4.
Can I pet your dog!?Annapolis, MD, 21403
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Chloe was absolutely amazing and provided loving care to our 3 fur babies! She sent updates and pictures daily while we were gone on vacation. Chloe followed fe… (more)

from
$75
per night
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Stacie Z.
5.
School Librarian who LOVES Dogs!Annapolis, MD, 21401
House Sitting, Drop-In Visits, Dog Walking

whenever I need someone to watch my dog, Stacie is the first person on my list to call. She cares for my dog Lucy as though she is her own. She more than feed… (more)

from
$65
per night
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6.
Vet tech, animal lover!Annapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking

Cayla was fantastic! She immediately bonded with our dogs, was timely, and gave us great updates with pictures while we were away. When we arrived home, our hou… (more)

from
$100
per night
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I love and am good with pets!Annapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking

Dominic is a very dependable dog walker. He always arrives on time. Our dog is very happy to go out with him. We highly recommend him. (more)

from
$50
per night
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8.
Pets are the glue of the familyStevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
8 years of experience

About: Ever since I was a child I have been responsible for taking care of many breeds from small dogs to extra large dogs. The duties included walking, fee… (more)

from
$40
per night
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Must love dogsAnnapolis, MD, 21403
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Gregory is the caring owner of an awesome dog and a cat. This is clear when he cares for others pets. We are confident that our cat gets the best possible ca… (more)

from
$40
per night
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10.
Dog lover all the wayAnnapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking

Jessica was a lovely house guest to have with our pups while we were away. This was our first time using her so she made sure to set up a time to meet before ou… (more)

from
$50
per night
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11.
Caring, Active, Dog WatcherAnnapolis, MD, 21403
House Sitting

Me and my husband were going on our anniversary trip and needed to find a house sitter for both our big dogs and cats. I’m so happy I found Amanda. She was so p… (more)

from
$150
per night
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Reliable & Responsible, Dog Lovers!Stevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, 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 we w… (more)

from
$28
per night
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I love animals!!Grasonville, MD, 21638
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hello! I am a work-from-home mom of 2 kids and a senior dachshund. I have worked in shelters and a cat sanctuary. I have also fostered dogs and cats … (more)

from
$30
per night
14.
All breeds welcomed and lovedStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Kasey house sat with my dog Charlie. She did a wonderful job and I will rebook again. She also sends tons of pictures of your dog while you’re away. (more)

from
$30
per night
15.
A animal lover of 19 years..Stevensville, MD, 21666
House Sitting, Dog Walking
16 years of experience

About: I’m an animal lover of 19 years owning and caring for 1 horse 3 dogs and two cats. I know how to properly play, handle, walk and bathe animals. You c… (more)

from
$35
per night
16.
love to workout with pupsStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Bhavani was awesome. Gunner and Magic were well taken care of. Thank you Bhavani! (more)

from
$65
per night
Calendar Recently Updated
I Love Furbabies!Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking

We were so very fortunate to have Bo sit for our dog while we were away. She endured rain storms, thunderstorms, fireworks, and much more, and did her absolute… (more)

from
$30
per night
18.
Pets Are My Passion!Grasonville, MD, 21638
House Sitting, Drop-In Visits, Dog Walking

Sarah was amazing with my cats and dog she treated them like her own and made me feel safe that they were in great hands. She played with them and made sure the… (more)

from
$27
per night
19.
Experienced pet sitter with loveStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

I have known Emmy for a while now, and never once would I doubt leaving my dog in her care. She has a heart of gold when it comes to animals, especially dogs, a… (more)

from
$45
per night
20.
Playful human wants to watch petsStevensville, MD, 21666
Dog Boarding, House Sitting, Doggy Day Care

Deborah is a caring person in every aspect of life but even more so when it comes to dogs. She has always been a dog lover and always had dogs of her own. When … (more)

from
$31
per night

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.