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.

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Seritta M.
I have a killer personality!!!Belaire-Edison, Baltimore, MD, 21213
House Sitting, Drop-In Visits, Dog Walking

Came through last minute and did a great job I will be rebooking (more)

from
$40
per night
Brandon B.
Vet Tech for new furry friendsAberdeen, MD, 21001
House Sitting, Drop-In Visits, Dog Walking

Brandon was amazing! I had a family emergency come up and really needed a sitter last minute for my senior dog while I dealt with things. I was super worried a… (more)

from
$50
per night
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Zachary B.
24/7 Dog-SittingEssex, MD, 21221
House Sitting, Drop-In Visits

Zachary is a kind, loving person who has never met a dog that didn't love him from the first moment they met! He is patient and dependable and will go above and… (more)

from
$40
per night
Elizabeth T.
Patient & attentive to their needs.Baltimore, MD, 21222
House Sitting, Drop-In Visits, Dog Walking

Elizabeth was wonderful house sitting little Toby. He had a wonderful time with her and her love of animals and sense of caring for his well being meant volumes… (more)

from
$55
per night
Hailey P.
5.
Love all animals of any species!North East, MD, 21901
House Sitting, Drop-In Visits, Dog Walking

Hailey is absolutely outstanding! My dog loved her and was treated as if her own. We felt completely comfortable with Hailey and hope we have a sitter for life! (more)

from
$60
per night
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6.
I'll treat your pet(s) like mine!Chestertown, MD, 21620
House Sitting, Drop-In Visits, Dog Walking

Jo was so great with our two anxious pups (and this anxious mom)! It was our first time leaving them and Jo was great with sending consistent pics and messages.… (more)

from
$65
per night
7.
Dog licks welcome!Edgemere, MD, 21219
House Sitting, Drop-In Visits, Dog Walking

Stacy took care of our dog for us at our home for four nights. She did a great job. Durango is older and has some anxiety issues. We did a meet and greet and… (more)

from
$55
per night
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8.
I’m a vet technician I love my jobBaltimore, MD, 21222
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ariana is a genuine and reliable and just a really great person. I wouldn't hesitate to recommend her and will absolutely be having her stay with Jinx again. It… (more)

from
$38
per night
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Leave your pet and safe handsDundalk, MD, 21222
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Heather did a fantastic job with both of my dogs, and was very respectful of my home while she was here. I would recommend her to anybody! GREAT JOB. (more)

from
$31
per night
A Pawsitive TailWagging ExperienceJoppa, MD, 21085
House Sitting, Drop-In Visits, Dog Walking

Can’t wait for Brittany to come back to visit Lacie and Chloe again she’s the best (more)

from
$31
per night
Sorry, that's dog hair! -Me, alwaysMiddle River, MD, 21220
House Sitting, Drop-In Visits, Dog Walking

Alex is smart, hardworking, caring and fun to be around. She will put your dogs first and make sure they get all the attention, treats (if allowed) and pets! … (more)

from
$35
per night
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Hello! Caring, loving, ready!Abingdon, MD, 21009
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
26 years of experience

About: Hello! I am a certified vet tech assistant who graduated in 2017 from Harford Community College. I own one dog named Lacy, an Australian Shepherd mix… (more)

from
$40
per night
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13.
I love dogs!Centreville, MD, 21617
House Sitting, Drop-In Visits, Dog Walking

We have used Rover.com a number of times over the past few years. Belen is on time, responsive, professional, and very caring to our animals. We would use he… (more)

from
$100
per night
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14.
Tim 
Verified Enhanced Background Check
All dogs are equalBelcamp, MD, 21017
House Sitting, Drop-In Visits, Dog Walking

I’ve had the worst time trying to find a pet sitter that could handle our German Shepard, Simba. The day Tim came over to meet him he had such a way with dogs t… (more)

from
$50
per night
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15.
I love loving on dogsEdgewood, MD, 21040
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I have known Takiara for 8 years. She is wonderful with pets. She has her own dog and treats him like a King. Her house is perfect setting for other dogs. V… (more)

from
$50
per night
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16.
Years of shelter experience!Essex, MD, 21221
House Sitting, Drop-In Visits, Dog Walking

Zach has cared for a family dog most of his life. He has fed them, walked them, given them baths and loved them. Zach's Eagle Scout project was an outdoor pavil… (more)

from
$31
per night
17.
Experienced with all types of dogsChestertown, MD, 21620
House Sitting, Drop-In Visits, Dog Walking

I used Becca for dog walking. She was on time and very professional and clearly loves animals. My dog loved her! I will definitely be using her again. (more)

from
$31
per night
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18.
i love animalsRock Hall, MD, 21661
House Sitting, Dog Walking

jaden l. is a good dog sitter. she watched my dogs for one month when i went to Nebraska to go and see my long distant cousins. and they were well-fed and got … (more)

from
$40
per night
19.
The best family member ever!Rock Hall, MD, 21661
House Sitting, Drop-In Visits, Dog Walking
30 years of experience

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 al… (more)

from
$100
per night
20.
Your Dogs New Best FriendMillington, MD, 21651
House Sitting, Drop-In Visits, Dog Walking
17 years of experience

About: I’ve been caring for animals, especially dogs from a very young age. I’ve always loved animals and every dog I’ve met we always get along. I have exp… (more)

from
$25
per night

Rover.com is the simple, savvy way to find and book Chestertown house sitting. It's easy to find the perfect house sitter — many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Chestertown on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Chestertown house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.