Pet Sitting in Chester

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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Michelle M.
Beautiful back yard for your dogs!Annapolis, MD, 21409
Dog Boarding, Drop-In Visits

Michelle has watched my energetic pup twice, and he’s come back tired and happy every time! She’s always very accommodating and has been flexible with pick-ups/… (more)

from
$35
per night
Calendar Recently Updated
Elaine Y.
2.
Eastport Doggie B&B!Annapolis, MD, 21403
Dog Boarding, Drop-In Visits

Elaine is awesome!! Ronnie is blind and fearful and a bit of a challenge sometimes. Elaine is so patient and kind with him. You can tell she really loves animal… (more)

from
$35
per night
Calendar Recently Updated
Bhavani K.
love to workout with pupsStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

My Eugene seemed to feel right at home with Bhavani and her dog, Ariana and I liked Bhavani immediately. After chatting with her for a bit, I could tell that sh… (more)

from
$35
per night
Karyn C.
4.
Comfort, Beach walks & lots of loveStevensville, MD, 21666
Dog Boarding, Drop-In Visits, Dog Walking

Karyn is everything you and your dog need in dog caregiver. She is reliable, experienced and truly loves and cares for all pets as if they were her own. I hig… (more)

from
$28
per night
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Deborah M.
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
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6.
May 
Verified Enhanced Background Check
Responsible, dog lover!Annapolis, MD, 21409
Dog Boarding, Doggy Day Care, Dog Walking

We had to travel away for 8 days and needed someone dependable for our Senior dog. We felt May could deliver that. She did an outstanding job accommodating our… (more)

from
$60
per night
Confirmed availability: Memorial Day
The Dog Sitter For YouAnnapolis, MD, 21401
Dog Boarding, Doggy Day Care

I am delighted with the way Makhayla watched over my pup. She was kind and kept me updated the whole time. This was my first time leaving him, and she made me f… (more)

from
$35
per night
Confirmed availability: Memorial Day
Pet Care Operations Manager 15yrsArnold, MD, 21012
Dog Boarding, Doggy Day Care, Dog Walking

Natalie was fantastic. She's clearly someone who has a lot of experience working with dogs as she knew all of the right questions to ask and considered everythi… (more)

from
$60
per night
Confirmed availability: Memorial Day
9.
All pups and kitties welcome!!Stevensville, MD, 21666
Dog Boarding, Dog Walking

Olivia was happy clean and we really appreciate the pictures! (more)

from
$25
per night
Confirmed availability: Memorial Day
A passion as deep as my soul🙏🏽Annapolis, MD, 21403
Dog Boarding, House Sitting, Doggy Day Care

Artis was fantastic, he took care of my dog (kofi) with no worries. He made sure I had updates and continued to communicate with me pictures the entire time. He… (more)

from
$50
per night
11.
Eva 
Verified Background Check
From one pet owner to anotherAnnapolis, MD, 21409
Dog Boarding, Drop-In Visits, Dog Walking

Our first time booking with Eva was paw-some! Eva offered care at an affordable rate and was super responsive from the get-go. She accommodated our request for … (more)

from
$25
per night
Calendar Recently Updated
12.
Caring pet sitterAnnapolis, MD, 21403
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Belle’s time with Laura and Bunny was great!! My baby was full of life and energy! She definitely enjoyed her time, and I felt very comfortable that she was in … (more)

from
$45
per night
13.
Canine's Cozy CottageArnold, MD, 21012
Dog Boarding

Sydney was amazing! So easy to schedule and set up a meet and greet Professional and thorough! Duncan had a great weekend with her and their dog Penny! She sen… (more)

from
$50
per night
“ Play, eat, nap, repeat!”Annapolis, MD, 21409
Dog Boarding, Doggy Day Care

Carolina gets an A+ in every category! She took great care of our pup, Lucy, sent us daily photos and updates, and was a great communicator. She's so kind, and … (more)

from
$40
per night
15.
Pet Nanny by trade!Glen Burnie, MD, 21638
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking
10 years of experience

About: I have been walking/sitting all sized dogs for 10+ years simply because dogs make me happier than anything else! I consider myself affordable so you … (more)

from
$31
per night
Confirmed availability: Memorial Day
Stay at home Mom and animal lover!Annapolis, MD, 21409
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

LOVE Ashley! I feel so grateful to have someone that I feel completely comfortable leaving Winston with. She makes drop-off and pick-up SUPER easy as she is alw… (more)

from
$35
per night
Calendar Recently Updated
Home Full Time + Fenced YardArnold, MD, 21012
Dog Boarding, Doggy Day Care

We love Luba and James ! This is the third time leaving Ella for up to a week and we couldn't be more pleased. Ella is a happy girl staying there and we are hap… (more)

from
$45
per night
18.
A+ Home w Active Dog & Fenced InGrasonville, MD, 21638
Dog Boarding

Tommy has been a wonderful dog owner to his pal Tucker for the last 6 years. Tucker is sociable, well cared for, and much of that is owed to Tommy’s training an… (more)

from
$35
per night
19.
All breeds welcomed and lovedStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

What a fantastic experience! Kasey was great! This was my first time leaving my rescue pup and I was totally put to ease thanks to the care she received. (more)

from
$30
per night
20.
Amy 
Verified Background Check
Love, Play, Make Them Feel At HomeAnnapolis, MD, 21401
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Would highly recommend Amy. She was wonderful and our dog loved his stay with her! She went above and beyond to make sure his stay was amazing but kept us updat… (more)

from
$60
per night

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Chester pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Chester, MD who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.