Pet Sitting in Chestertown

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Sitter Profile Image: Heather H.
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Sitter Profile Image: Heather H.
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1.

Heather H.

Leave your pet and safe hands
Dundalk, MD, 21222
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
26 reviews
12 repeat clients
from
$16
per visit

First time using Rover and Heather was wonderful. We appreciated her being patient and flexible with us. Our babies were well taken care of and we hope to be able to use Heather’s services again in the future ?

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Sitter Profile Image: Makelle A.
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Sitter Profile Image: Makelle A.
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2.

Makelle A.

Here to love on your babies!
Aberdeen Proving Ground, MD, 21005
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
2 reviews
from
$14
per visit

Makelle loved on my fur baby, Willie, for one whole month while I was away for military training. I never once had to worry about my dog while I was gone. She was very good at giving updates and even sending pictures. I have no doubt that she would love on your pets just like mine. Highly recommend!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Mariah W.
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Sitter Profile Image: Mariah W.
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3.

Mariah W.

Always play time !
Edgewood, MD, 21040
Drop-In Visits, Dog Walking
5.0
87 reviews
23 repeat clients
from
$15
per visit

I can’t say enough good things about Mariah and my experience with her. She made me feel so at ease with her detailed updates and her funny comments in the updates. My cats might prefer her over me!

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Sitter Profile Image: Jacquelyne E.
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Sitter Profile Image: Jacquelyne E.
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4.

Jacquelyne E.

Passionate animal lover
Abingdon, MD, 21009
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
8 reviews
from
$18
per visit

Jacquelyne has an excellent understanding of cats and has the patience to care for them too. Her scheduling flexibility helped me take care of my cat during the hectic time of a wedding. I will definitely ask her again to take care for my pet.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Joanne G.
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Sitter Profile Image: Joanne G.
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5.

Joanne G.

I am the voice for animals
Middle river, MD, 21220
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
1 review
from
$14
per visit

She sent videos daily, kept in touch with fun things they did while she was there. She was wonderful, would recommend her to others for sure

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Heather & Jennifer T.
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Sitter Profile Image: Heather & Jennifer T.
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6.

Heather & Jennifer T.

Trusted Pet Care Provider
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
5.0
12 reviews
3 repeat clients
from
$20
per visit

My family takes trips out of town to see my in-laws and the past few times we've had Heather watch our dog Cody. She is fantastic with him and he always gets so excited when she comes to see him! He is a very active dog and she has been willing to take him on nice long walks to help him get his energy out. She is 100% our go-to person to take care of Cody when we have to take short trips!

Sitter Profile Image: Marissa H.
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Sitter Profile Image: Marissa H.
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7.

Marissa H.

Pet mama to the rescue
Chestertown, MD, 21620
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
3 repeat clients
from
$20
per visit

Marissa took great care of our 4 cats! We didn’t have to worry about them while we were away. I’d recommend Marissa to anyone looking for a pet sitter.

Sitter Profile Image: Heidi K.
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Sitter Profile Image: Heidi K.
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8.

Heidi K.

Just like family!
Belcamp, MD, 21017
House Sitting, Drop-In Visits, Dog Walking
5.0
13 reviews
4 repeat clients
from
$20
per visit

This is the second time we’ve used Heidi and she is great with our doggies. She sends lots of pictures and makes us feel like our pups are getting love when we can’t be there. Would recommend her and continue to use her when she is available.

Sitter Profile Image: Stacy H.
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Sitter Profile Image: Stacy H.
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9.

Stacy H.

Dog licks welcome!
Edgemere, MD, 21219
House Sitting, Drop-In Visits, Dog Walking
5.0
56 reviews
15 repeat clients
from
$35
per visit

Stacy is our GO TO petsitter for our cat Maggie. Maggie is basically a dog living in a cat's body - she will come running to greet people at the door. Stacy is great about sending pics and videos and paying extra special attention. She is also a wonderful pair of eyes on the house while we are away.

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Sitter Profile Image: Taylor E.
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Sitter Profile Image: Taylor E.
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10.

Taylor E.

I care for all animals
Earleville, MD, 21919
House Sitting, Drop-In Visits, Dog Walking
1 year of experience
from
$20
per visit

About: I’m a veteran, and a current college student. I have a part time job. My schedule is very flexible and whatever my clients need I will ensure I accomplish. I absolutely love animals of all kinds. My degree is in wildlife science I have off Monday, Thursday, Saturday, and Sunday. All other days I am working. I can stop by in the morning and afternoon to take care of your pets. I have no problem staying throughout the week. I just need to leave for college and my job. Whatever works for my clients I will accommodate. I understand that having a stranger in your home and caring for your pet can be uncomfortable. I promise to be respectful to your home and rules. I will be very loving to your pet. Whatever needs and wants you have just let me know and I ensure to accomplish it.

Sitter Profile Image: Sammy S.
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Sitter Profile Image: Sammy S.
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11.

Sammy S.

They leave paw prints on your heart
Essex, MD, 21221
House Sitting, Drop-In Visits, Dog Walking
5.0
1 review
from
$30
per visit

About: I’ve been taking care of dogs since I was 5. We have always had a dog in the house and I’ve worked with many different breeds. I have helped feed, bathe, walk and train many dogs in the past few years. I currently have a 8 month old puppy that I am training and I have three other dogs that live in the house that I help take care of! I recently lost my one pup right after thanksgiving that I rescued about 9 1/2 years ago. He was my first pup I owned myself and he was a great dog! Missing him has been very hard and I would to share my love for animals with yours like I did with him!! I’m currently working part-time and going to college so I have time on the weekends to play and cuddle your fur babies! I am available anytime on Saturday's and am available early morning to mid afternoon on Sunday’s! I have a fenced in yard and have 3 dogs that love to run around in it. I have a 8 month old lab at my friends house that we share and he has a nice sized yard he likes to play fetch in and there is a leash stacked in there.

Sitter Profile Image: Callie C.
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Sitter Profile Image: Callie C.
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12.

Callie C.

Rover 101
Live, Love, Bark!
Grasonville, MD, 21638
House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
1 repeat client
from
$30
per visit

Usually I am skeptical about leaving Sasha, my two year old husky with a sitter due to her separation anxiety(on top of her off-the-chain energy levels) but I can definitely say I was impressed with Callie's level of commitment to my pup. Sasha came back to me not only with a literal smile on her face but with an almost confliction to leave her new friends behind. I will certainly be bringing her back soon.

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Sitter Profile Image: Khadijah G.
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Sitter Profile Image: Khadijah G.
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13.

Khadijah G.

Rover 101
Your Weekend Sitter !
Chestertown, MD, 21620
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
20 reviews
6 repeat clients
from
$30
per visit

Khadijah has came over a few times now to let our 75 lb Lab/Pit/Setter Mix out and Feed him on our long work days. Khadijah came and took the time out of her own, to come over and meet us and Clarke, ahead of time before we even booked her, to make sure all would be okay. It really was to ease moms nerves cause I know he can be a lot to handle sometimes and a big baby when it comes to eating when we aren’t there. She has stayed over her time allotted just to make sure he eats completely, and goes to the bathroom. I really thank Khadijah for her help and recommend her to anyone and any big dog!

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Sitter Profile Image: Sabrina G.
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Sitter Profile Image: Sabrina G.
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14.

Sabrina G.

Personalized Pet Care Specialist
Wye Mills, MD, 21640
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4.5
12 reviews
4 repeat clients
from
$25
per visit

Sabrina is a very conscientious dog owner. They have 3 dogs of their own that are all rescues. She has fostered problem dogs for a local rescue and taught them to behave so that they were adoptable.

Sitter Profile Image: Joy P.
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Sitter Profile Image: Joy P.
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15.

Joy P.

Can't imagine my life without a dog
Kennedyville, MD, 21645
Drop-In Visits, Dog Walking
5.0
1 review
from
$20
per visit

About: I love dogs very much . Had them all of my life. I have 2 labs which are very spoiled. I would take very good care of your pet like it was my own. I am available on weekends or Friday and Saturday nights.Sunday during the day. I can come walk your dog during the day and evening on weekends and spend as much time with them as you like. I have a house with a fenced in yard out in the country. I have 2 acres. I would love too spend some time with your furry friends.I have been around animals all of my life. Can't imagine not having animals in my life. My dogs are always glad to see me when I get home and always put a smile on my face.

Sitter Profile Image: Ryan M.
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Sitter Profile Image: Ryan M.
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16.

Ryan M.

I just love hanging out with dogs
Chestertown, MD, 21620
Drop-In Visits, Dog Walking
3 years of experience
from
$20
per visit

About: I’ve taken care of my own dog for the last 3 years, including bathing, walks, and plenty of play. I’ve also cared for friends’ dogs I am a college student right now but I am on Summer break so I am very flexible when it comes to scheduling and short-notice asks I will follow owner’s instructions when in their homes and interacting with their dogs. I am comfortable walking any well behaved dog on a leash as well as crating and feeding as long as I am made aware of their needs

Sitter Profile Image: Jordan D.
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Sitter Profile Image: Jordan D.
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17.

Jordan D.

Caring, Loving, and Playful
Centreville, MD, 21617
House Sitting, Drop-In Visits, Dog Walking
14 years of experience
from
$20
per visit

About: I have had dogs and cats ever since I was little. Currently I have a cat named Mina, and a lab named Nelli. Mina likes to sun bathe outside and play with her laser while Nelli loves to be outside and wants to play all the time. I also am established with a few clients with dropping in to check on their fur baby, take them on walks, and feeding, as well as, overnight stays to make sure the fur babies are well taken care of while their parents are out. I do work full time, but I have an hour lunch where I use to drop in on the fur babies, play with them, or even just eat lunch with them. I work 8-5 mon-fri so weekends are full of fun! I do not bring other animals to my house as introductions do not always go well. I do however stay overnights at the clients house. This also keeps the stress levels of the fur babies down while their parents are away.

Sitter Profile Image: Jaden L.
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Sitter Profile Image: Jaden L.
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18.

Jaden L.

i love animals
rock hall, MD, 21661
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
from
$35
per visit

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 a lot of excercise.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Isabel O.
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Sitter Profile Image: Isabel O.
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19.

Isabel O.

Keep those doggy tails wagging!
Wye Mills, MD, 21625
Drop-In Visits, Dog Walking
5.0
3 reviews
from
$25
per visit

Isabel is amazing. She responded in a matter of minutes last week when I needed a last minute appointment to take care of my two German Shepherds. She took the time to stop by and meet them before we went out of town and then did an amazing job taking with drop-in visits while we were away. Highly recommended!

Sitter Profile Image: Sam M.
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Sitter Profile Image: Sam M.
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20.

Sam M.

Quality care for the pets you love!
Chestertown, MD, 21620
House Sitting, Drop-In Visits, Dog Walking
4.0
1 review
from
$15
per visit

Sam was great. He really took the time to make sure he understood how to care for our cat. He is responsive and reliable. Thanks Sam!

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Chestertown Pet Sitting & Drop Ins ratings

Overall Rating:

Pet sitters in Chestertown are rated on average 4.8 out of 5 stars based on 30 reviews.


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Chestertown pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Chestertown, MD, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Chestertown pet sitters and avoid the kennel.

Drop-In Visits