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.
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Rachel G.
1.
Bet I can make your dog’s tail wag!Annapolis, MD, 21401
House Sitting, Drop-In Visits, Dog Walking

We were new to Annapolis and have three kitties and two doggies. A couple of our furry kids are seniors and need special care. One kitty receives subcutaneous … (more)

from
$65
per night
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Wendy C.
2.
Pet Lover to the Rescue!!Edgewater, MD, 21037
House Sitting, Drop-In Visits, Dog Walking

Wendy was great! I was neurotic and left a million details and she was so patient and kind. She sent me pics and gave me updates which was what i needed to enjo… (more)

from
$40
per night
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Michaila M.
I’m happy to meet new furry friendsAnnapolis, MD, 21401
House Sitting, Drop-In Visits, Dog Walking

Michaila is wonderful. She is diligent with being on time, keeping home neat and staying in touch with me regarding my Jasper. I also had a schedule change the … (more)

from
$40
per night
Eric R.
4.
Been dog sitting since I was 12Annapolis, MD, 21409
House Sitting

After reading his profile and reviews from others I selected Eric. Eric is a very nice professional young man who communicates well. He came over to see my pups… (more)

from
$32
per night
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Terri J.
5.
Dedicated to your pets well being!Annapolis, MD, 21401
House Sitting, Drop-In Visits, Dog Walking

Second stay with Terri down and it was as much of a pleasure as the first. I entrust her with taking care of our home and beloved (and wild, yet lovable) pup. N… (more)

from
$40
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
$30
per night
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7.
No life is complete without a dogAnnapolis, MD, 21401
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Warren is a kind-hearted, loving, and caring individual that is amazing with animals! He is the responsible and trusting person you would be more than comfortab… (more)

from
$35
per night
Confirmed availability: Memorial day
All dogs WelcomeWittman, MD, 21676
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kymberly was wonderful with Lola. She was highly responsive to our changing needs. We look forward to having her watch Lola again! (more)

from
$45
per night
I Love Furbabies!Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking

Bo & Rowdy forever! Bo is wonderful this time we had a little ant problem while we were away and she was nice enough to go buy ant traps to take care of the… (more)

from
$30
per night
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10.
Best Buddy for the Furry RoyaltyAnnapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking

About: My brother was our black Lab named Jabip! Mom brought him home when I was 3 days old! So I feel a deep connection to dogs! Then at 6 years old, we mo… (more)

from
$35
per night
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11.
Spent my life caring for fur babiesAnnapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking

I know that when I leave my service dog Ah'mie with Hope that she will be well taken care of. Hope's concerns for Ah'mie's health, happiness and well being are… (more)

from
$31
per night
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12.
Caring, Active, Dog WatcherAnnapolis, MD, 21403
House Sitting, Drop-In Visits, Dog Walking

Amanda was great with our 2 dogs and cat. She was super communicative and flexible. I felt super comfortable leaving my house and animals in her care for over a… (more)

from
$50
per night
13.
ER Vet Tech w/ Pet Sitting ExpStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: Thank you for taking the time to review my profile. I am a mother to both dogs and humans! I've served as a vet tech off and on in the field for 10 y… (more)

from
$70
per night
14.
frequent exercise and attentionAnnapolis, MD, 21409
House Sitting, Drop-In Visits, Dog Walking

I've know Hannah for a very long time. She is the perfect person to pet sit. She has a genuine love, passion and heart for animals. She's been helping our fa… (more)

from
$70
per night
Confirmed availability: Memorial day
15.
Experienced Dog Lover AvailableAnnapolis, MD, 21409
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I've owned both big and little dogs and love them all. I enjoy taking the dogs I look after to the park for nice long walks in nature. I also make su… (more)

from
$55
per night
16.
I'll Love Your Pets Like My OwnAnnapolis, MD, 21409
House Sitting, Drop-In Visits, Dog Walking

Sara is great! I'm military and cant be home certain days and she was very accommodating. I have a little ball of terror and she was great with him! She kept me… (more)

from
$25
per night
17.
Experience in Veterinary AssistanceStevensville, 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 swee… (more)

from
$75
per night
18.
Physical Therapist, Dog LoverQueenstown, MD, 21658
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi There! My name is Leah and I am a Physical Therapist and Personal Trainer with a big heart for animals. I currently work for AAMC on Kent Island.… (more)

from
$75
per night
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19.
Honest, gentle and friendlyGrasonville, MD, 21638
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Pam actually babysits for our human 3 year-old, so while he isn't a dog, he takes a lot of care :). Pam is loving and responsible and our son asks for her. This… (more)

from
$40
per night
Confirmed availability: Memorial day
Excited to Help Out!Chester, MD, 21619
House Sitting, Drop-In Visits, Dog Walking

Madeline did an excellent job taking care of Bella and Obi. Pups were happy and well fed. We will definitely use her again! (more)

from
$30
per night

Rover also offers House Sitting in:


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.