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.
Calendar Recently Updated
Stacy H.
1.
Dog licks welcome here!Edgemere, MD, 21219
House Sitting, Drop-In Visits, Dog Walking

She was GREAT! Very pup friendly. She evn came the meet the pups prior to leaving them in her care. Got lots of pics/videos while we were away. Pups seemed ha… (more)

from
$45
per night
Calendar Recently Updated
Erika & Nikita H.
Your Fur Babies are FAMILY!Cedonia, Baltimore, MD, 21206
House Sitting, Drop-In Visits, Dog Walking

Erika continues to be fabulous. She really cares and took great care of Dip while I was away. Erika provides pics and good updates throughout her stay. I feel c… (more)

from
$45
per night
Confirmed availability: Memorial day
Evelyn R.
3.
I’ll run with your dog!dundalk, MD, 21222
House Sitting, Drop-In Visits, Dog Walking

Evelyn did an amazing job caring for our pets. We went away for 3 days and she did exactly what we asked of her. Her rates are pretty low compared to the work s… (more)

from
$40
per night
Calendar Recently Updated
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
Calendar Recently Updated
Andrew G.
5.
Celtic CaretakingCanton, Baltimore, MD, 21231
House Sitting, Drop-In Visits, Dog Walking

Andrew took such great care of my 10 mo AmStaff rescue who has separation anxiety. He brought tons of toys, most of which were enrichment toys, and also put on … (more)

from
$33
per night
Calendar Recently Updated
6.
Animal lover ❤️Middletown, DE, 19709
House Sitting

Just love Bailey, she arrived early and was very communicative during my overnight away! Will definitely use her again and highly recommend her! Thanks Bailey!! (more)

from
$30
per night
Calendar Recently Updated
7.
Hard-working, energetic, kindBaltimore, MD, 21234
House Sitting, Drop-In Visits, Dog Walking

Anybody would be lucky to have Marlo as their pet sitter! When I first met Marlo we were out to dinner with our friend and her dog -- I couldn't believe how goo… (more)

from
$55
per night
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
Confirmed availability: Memorial day
9.
Dog LoverTownsend, DE, 19734
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Mike made our first ROVR experience a good one. He was reliable and communicative. It gave us great peace of mind to know that our furry family members were in … (more)

from
$30
per night
10.
Happy home for happy pups.Baltimore, MD, 21206
House Sitting, Drop-In Visits, Dog Walking

Nate was a super awesome house sitter for Boomer; he was a very trustworthy guy to leave in your house! He was very fast to respond to my request and be availa… (more)

from
$40
per night
Calendar Recently Updated
11.
Lover of all pets big and small!abingdon, MD, 21009
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Peyton has taken care of two dogs for our family--a senior dog with medical needs and most recently a rescue with extreme separation anxiety undergoing heartwor… (more)

from
$30
per night
Confirmed availability: Memorial day
12.
Experienced and reliable pet sitterCentreville, MD, 21617
House Sitting, Drop-In Visits, Dog Walking

Rachel is super sweet and loving to my animals! I would recommend her services !! (more)

from
$55
per night
Pets are family too!!Abingdon, MD, 21009
House Sitting, Drop-In Visits, Dog Walking

Fantastic job Very happy with Fontayne. I will definitely use her again (more)

from
$40
per night
Calendar Recently Updated
14.
Young Adult Nursing StudentWye Mills, MD, 21679
House Sitting, Drop-In Visits, Dog Walking

Very friendly and took excellent care of our dogs. HIGHLY RECOMMENDED (more)

from
$35
per night
Confirmed availability: Memorial day
15.
Your pet will be treated with careEdgewood, MD, 21040
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi my name is Tanya and you can follow me on IG @tanyaspethouse. I have a lot of pets such as dogs, cats, gerbils, guniea pigs, rabbits, fish, parake… (more)

from
$35
per night
16.
Animal loving college studentChestertown, MD, 21620
House Sitting, Drop-In Visits, Dog Walking

Ashley is a mature responsible young adult with very strong arms. She can walk the most unruly dog and he’s like a puppy with her. All animals seem to go to her… (more)

from
$50
per night
17.
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
18.
super flexible scheduleChestertown, MD, 21620
House Sitting, Drop-In Visits, Dog Walking

Agnes was great with our pup Charlie! It’s always hard to find someone who has availability for the holidays and she was so flexible! Charlie had a great time a… (more)

from
$50
per night
19.
Fun, gentle, and loving pet care!Centreville, MD, 21617
House Sitting, Drop-In Visits, Dog Walking

About: Being a college student in 2020 means sitting in the same room all day long. I figured I would take my love for pets and my need for exercise to beco… (more)

from
$28
per night
20.
They are family not pets.Rock Hall, MD, 21661
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

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
$25
per night

Rover also offers House Sitting in:


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.