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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Search Results

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Heather H.
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Sitter Profile Image: Heather H.
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1. Heather H.

Star Sitter
Leave your pet and safe hands
Dundalk, MD, 21222
22.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
32 reviews
16 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 ?

Sitter Profile Image: Sophie E.
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Sitter Profile Image: Sophie E.
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2. Sophie E.

Thank you for visiting my page!
Chestertown, MD, 21620
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$20
per visit

Sophie has taken care of my dog Charlie many times including overnight. I have never once questioned his safety or if he was relaxed and happy. My dog has severe anxiety issues which is why we do not board home when we go away. If you are lucky enough to get Sophie to take care of your fur baby you will honestly not want anyone else to take on this responsibility. She is kind, caring, has a very gentle demeanor. Charlie, my husband and myself are very thankful for her.

Sitter Profile Image: Marissa H.
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Sitter Profile Image: Marissa H.
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3. Marissa H.

Pet mama to the rescue
Chestertown, MD, 21620
5.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$20
per visit

Marissa is caring and reliable. She has been my regular cat sitter for more than 6 months and my cat is much happier for it. She is a great communicator and always sends cute pictures when she does her visits.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Mariah W.
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Sitter Profile Image: Mariah W.
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4. Mariah W.

Star Sitter
Always play time !
Edgewood, MD, 21040
20.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
95 reviews
29 repeat clients
from
$15
per visit

We’ve been having Mariah drop in a few days a week to check in our dogs for the last few weeks and we HIGHLY recommend her. The dogs seem to love her and seem happier overall with their 30 minute drop ins. I trust Mariah with my babies (which normally takes a lot) and I really appreciate how communicative she is about her visit with them. If you’re looking for someone trustworthy and responsible to care for your dogs, Mariah is your girl!

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Sitter Profile Image: Gail C.
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Sitter Profile Image: Gail C.
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5. Gail C.

Care for your furbabbies like my ow
Cordova, MD, 21625
23.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
5 repeat clients
from
$19
per visit

Our cats seemed perfectly happy and calm when we arrived home. Gail did a great job caring for them and was super nice about changing dates when our trip plans changed.

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Sitter Profile Image: Tori V.
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Sitter Profile Image: Tori V.
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6. Tori V.

Caring animal lover
Centreville, MD, 21617
6.7 mi. away
Drop-In Visits, Dog Walking
1 review
from
$20
per visit

Tori is a fantastic dog lover , who will treat your dog as if her own. I have known Tori for 8 years , and I would trust her with my babies any day ! She is outgoing , knowledgeable, and kind !

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jacquelyne E.
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Sitter Profile Image: Jacquelyne E.
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7. Jacquelyne E.

Star Sitter
Passionate animal lover
Abingdon, MD, 21009
21.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
2 repeat clients
from
$25
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: Memorial Day Weekend
Sitter Profile Image: Jadia A.
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Sitter Profile Image: Jadia A.
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8. Jadia A.

Your local animal lover!
Aberdeen Proving Ground, MD, 21005
19.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$19
per visit

I’ve know Jadia Armstrong for 12 years and she is a complete animal lover. She has pet sit for me and her parents plenty of times and they were in excellent care. Even when she was in the military when her coworkers were on leave they would ask her to watch their fur babies and she’d do it with no pay too. Your animals are in excellent hands with her!

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Sitter Profile Image: Jada C.
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Sitter Profile Image: Jada C.
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9. Jada C.

I LOVE ANIMALS!!!
Middle river, MD, 21220
19.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$18
per visit

Jada is awesome Ive never left my baby with anyone but my mother, unfortunately I needed to find care for her. Jada responded promptly to my message. She was more than willing to meet up with me before caring for bella. The day she let bella out she sent me pictures and kept me updated while she was with her so I knew she was safe. I definitely will use her again and would recommend her to anyone looking.

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Sitter Profile Image: Deanna P.
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Sitter Profile Image: Deanna P.
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10. Deanna P.

I love animals, there family.
Greensboro, MD, 21639
21.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$14
per visit

Deanna is so wonderful! My senior dog Bella and cat Pete reqiire medication and alot of attention, and Deanna goes above and beyond making sure they both are very happy. Also,she sends me updates and pictures on every visit so I'm at ease.😊

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Sitter Profile Image: Nancy A.
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Sitter Profile Image: Nancy A.
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11. Nancy A.

A caring dog sitter
Baltimore, MD, 21220
21.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 years of experience
from
$25
per visit

About: I am fairly new with dog sitting but have received great reviews from friends. They have relied on me to walk, feed, and spend the night with their dogs. My availability includes evenings after 5pm on weekdays. The entire weekend including Friday evening-Sunday evening. I am willing to be more flexible with advance notice. I care for pets at their own home. I want the pets to be comfortable and typically that is at their own with access to their everyday needs.

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Sitter Profile Image: Abigail & Tausha M.
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Sitter Profile Image: Abigail & Tausha M.
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12. Abigail & Tausha M.

AWESOME PETSITTING IN YOUR HOME!
Chestertown, MD, 21620
2.0 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$25
per visit

When I need someone to look after my three fur babies, I call Abby. She is always on time, and looks after my dogs as if they were her own. My dogs love her probably more than me. Lol. Abby is rare in the industry. She has watched my dogs over extended periods of time as work takes me out of town frequently. They get the care they need and deserve. One thing I never have to worry about is my dogs. Go with her. You won’t be disappointed.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Takiara W.
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Sitter Profile Image: Takiara W.
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13. Takiara W.

I love loving on dogs
Edgewood, MD, 21040
18.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
28 reviews
13 repeat clients
from
$15
per visit

What a wonderful and caring person!! I just love how she interacts with Fluffy. Since day 1 I've noticed how Takiara is always attentive and comfortable with dogs. Thank you again for the companionship you've provided!

Sitter Profile Image: Heidi K.
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Sitter Profile Image: Heidi K.
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14. Heidi K.

Just like family!
Belcamp, MD, 21017
20.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$18
per visit

Heidi was amazing with King!! She was very attentive, always on time, and was great with communicating and sending pictures of King. We will definitely be looking to use Heidi again!

Sitter Profile Image: Sabrina G.
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Sitter Profile Image: Sabrina G.
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15. Sabrina G.

Personalized Pet Care Specialist
Wye Mills, MD, 21640
18.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4.5 out of 5 stars
15 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.

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Sitter Profile Image: Nicole M.
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Sitter Profile Image: Nicole M.
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16. Nicole M.

Flexible schedule,
Millington, MD, 21651
14.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$15
per visit

Since 2015, Nicole has been my dedicated and beloved pet sitter, and I feel incredibly fortunate to have found her. Her commitment to caring for my Pittie has been truly exceptional, as she possesses a remarkable understanding of their unique personalities, even when they're spirited. Witnessing the incredible progress my dog has made under her watch, I decided to enroll in her training program. Our affection for her has only grown over the years. As my pup enters her golden years, Nicole's compassion and affection for her have deepened, and she consistently shows remarkable patience in her care. Furthermore, Nicole has generously offered numerous overnight stays for my Bella, going the extra mile with pick-ups and drop-offs to accommodate my busy schedule. Undoubtedly, Nicole has enriched both Bella's and my life in a profoundly heartwarming manner, and she even sends pictures without me having to ask! Finding her was one or the most important and best decisions of my life! She's worth every dollar!

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Sitter Profile Image: Lisa M.
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Sitter Profile Image: Lisa M.
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17. Lisa M.

Over 30 years experience!
Ridgely, MD, 21660
18.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
30 years of experience
from
$25
per visit

About: I’m a lifelong animal owner and “farm girl” with experience owning and working with dogs, cats, small animals, livestock, and even exotics. I previously worked as a small and large animal veterinary nurse. I am a full time teacher available early mornings and evenings on weekdays with more daytime flexibility during breaks and summer months. During the school year I am limited to before and after school hours. I care for your animal as if they were my own! I am attentive to your animal’s needs and will make sure to do things “your way” in order to keep your pet’s routine as consistent as possible!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jordan D.
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Sitter Profile Image: Jordan D.
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18. Jordan D.

Caring, Loving, and Playful
Centreville, MD, 21617
11.8 mi. away
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: Joy P.
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Sitter Profile Image: Joy P.
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19. Joy P.

Can't imagine my life without a dog
Kennedyville, MD, 21645
8.9 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
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.

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Sitter Profile Image: Jaden L.
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Sitter Profile Image: Jaden L.
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20. Jaden L.

i love animals
rock hall, MD, 21661
9.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
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.

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Chestertown Pet Sitting & Drop Ins ratings

Overall Rating:
4.8 out of 5 stars

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

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Chestertown:


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