House Sitting in Chestertown

Find a loving dog sitter to watch your dog overnight in your home.

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Boarding
House Sitting
Drop-In Visits
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Sitter Profile Image: Jaime A.
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Sitter Profile Image: Jaime A.
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1.

Jaime A.

Make them happy while your away!
Millersville, MD, 21108
28.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
44 reviews
19 repeat clients
from
$72
per night

Jaime took great care of my two labs and home while I was away for 5 days. He communicated regularly with pictures easing my mind that all was well. He left goodie bags for the dogs - a very kind gesture. Jaime is a stellar sitter who I highly recommend.

Confirmed availability: Easter Weekend
Sitter Profile Image: Louise D.
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Sitter Profile Image: Louise D.
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2.

Louise D.

I'm a loving caring animal person
Easton, MD, 21601
27.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
4 repeat clients
from
$28
per night

Louise was amazing! She updated me along the way and took care of my dog while I was out of town! She responded quickly and made sure to send pics of my dog so I didn’t worry about her!! Highly highly recommend!!!!!

Sitter Profile Image: Heather H.
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Sitter Profile Image: Heather H.
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3.

Heather H.

Leave your pet and safe hands
Dundalk, MD, 21222
22.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
15 repeat clients
from
$60
per night

Heather was incredibly lovely with our two dogs all weekend! She was kind, conscientious, and communicative. She sent many pictures and updates and was an overall joy to have with our pups. She even came back to check on them when we were delayed getting home. Highly recommend!!

Sitter Profile Image: Sophie E.
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Sitter Profile Image: Sophie E.
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4.

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
$40
per night

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.

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Sitter Profile Image: Reed C.
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Sitter Profile Image: Reed C.
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5.

Reed C.

Years of experience and love!
Joppa, MD, 21085
19.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
from
$38
per night

Reed absolutely exceeded all expectations with his pet sitting services for my dynamic duo, Atlas and Phillip! From the moment we connected, his enthusiasm for pet care was contagious. It’s clear that my pets were showered with love, attention, and plenty of belly rubs. He was very respectful of our house and the updates and photos they provided melted my heart and reassured me that my fur babies were in the best hands possible. I wholeheartedly endorse Reed for anyone seeking passionate, top-notch pet care!

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Sitter Profile Image: Cristina M.
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Sitter Profile Image: Cristina M.
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6.

Cristina M.

Cat & Dog Whisperer for hire!
Stevensville, MD, 21666
19.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$75
per night

Cristina is likely the best choice for your pet! You likely won't find a more loving and caring caregiver for your pet. I have two little shih tzus that usually stay right with me... but they just light up whenever Cristina comes into the house and she has their full attention - and importantly, they get her full attention :)

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Sitter Profile Image: Jacquelyne E.
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Sitter Profile Image: Jacquelyne E.
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7.

Jacquelyne E.

Passionate animal lover
Abingdon, MD, 21009
21.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
1 repeat client
from
$35
per night

Jacquie was wonderful! Sent lots of pics, communicated very well, and our Lucy girl was happy as a clam!

Sitter Profile Image: Joe C.
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Sitter Profile Image: Joe C.
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8.

Joe C.

Works from home, available anytime!
Essex, MD, 21221
23.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$55
per night

Joe is a close friend that my dogs adore. They are both rescues and don’t open up to many people but from the first day they met him they wanted to be by his side. Now when he visits they want to play for hours and even lay on his feet to make sure he doesn’t leave lol

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Sitter Profile Image: Lisa M.
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Sitter Profile Image: Lisa M.
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9.

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
$40
per night

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!

Sitter Profile Image: Abigail & Tausha M.
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Sitter Profile Image: Abigail & Tausha M.
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10.

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
9 reviews
3 repeat clients
from
$40
per night

Abby and Tee are awesome! One of our doggos is super anxious and was a bit of a handful to start, and Abby and Tee handled it all with such grace and patience. Great communication as well!

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Sitter Profile Image: Samantha B.
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Sitter Profile Image: Samantha B.
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11.

Samantha B.

Tailored care for four-legged fam
Felton, DE, 19943
22.4 mi. away
House Sitting, Drop-In Visits
20 years of experience
from
$35
per night

About: Looking for a reliable and experienced pet sitter? Look no further! With a lifetime of love for animals, I'm here to provide top-notch care for your dogs, cats, and even reptiles. My passion for pets means your furry (or scaly) family members will receive the best possible attention while you're away. Feel free to ask any questions you have, I'm always happy to chat about your four-legged (or scaley) loved ones! I am currently taking time off from being a mobile therapist while obtaining my bachelors in psychology. I work part time with friends, and am looking for some additional income! Building on my expertise: While juggling my Bachelors in Psychology studies, I'm eager to leverage my experience in (mobile therapy/related skills) into fulfilling part-time work. Open to diverse opportunities!

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Sitter Profile Image: Deanna P.
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Sitter Profile Image: Deanna P.
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12.

Deanna P.

I love animals, there family.
Greensboro, MD, 21639
21.9 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$31
per night

Another good visit with Deanna!🙂

Sitter Profile Image: Brittany G.
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Sitter Profile Image: Brittany G.
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13.

Brittany G.

A Pawsitive TailWagging Experience
Joppa, MD, 21085
22.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
7 repeat clients
from
$37
per night

Brittany was the saving grace for my wedding weekend when my original sitters fell through! She came over for a meet and greats fees before and spent the evening with my little old man sending me pics through the night. She was tidy and I felt very safe leaving my pup with her on what was already a crazy day! Will hire again!

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Sitter Profile Image: Abigail C.
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Sitter Profile Image: Abigail C.
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14.

Abigail C.

Local Pawsitively Perfect Care
Worton, MD, 21678
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
from
$25
per night

We — and most importantly our dogs — love Abigail. It’s crucial to find someone you’re comfortable with when leaving your pets and your home in their care. We couldn’t be happier with her.

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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
$40
per night

Sabrina did a great job taking care of our 4-month-old puppy, Wednesday, and our kitty, Xander. She played with our puppy and let her out a bunch while she’s still potty training. She gave our cat some love, giving him company while our pets are still separating during their time still getting to know each other. It definitely helps us put our minds at ease when we leave for another trip knowing that they’ll be in great hands! :)

Sitter Profile Image: Marissa H.
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Sitter Profile Image: Marissa H.
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16.

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
7 reviews
4 repeat clients
from
$50
per night

About: Hi! I’ve taken care of dogs and cats since I was 5! I’ve had small dogs all the way up to 115 pound dogs. I absolutely adore cats as well! I am able to take care of lizards as well! I have also dealt with very aggressive dogs which do not scare me! I currently work part time at a hair salon which leaves me with a lot of extra time on my hands. I will be able to take care of your pets from morning until afternoon and then when I get off at 7 ( which are my late nights twice a week ) I’m willing to stay at my clients home so the pet will be less stressed and in their home. I am a full time pet mama so I will be able to help in so many ways! Please feel free to message me with any questions or request. I would love to send video / photos of daily doses of your pet to you!

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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
11.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
14 years of experience
from
$60
per night

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
9.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$50
per night

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.

Sitter Profile Image: Joanna G.
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Sitter Profile Image: Joanna G.
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19.

Joanna G.

I'll treat your pet(s) like mine!
Chestertown, MD, 21620
0.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
2 repeat clients
from
$85
per night

Joanna was wonderful. My dog loved her from the moment she met her. Joanna was very responsive and communicative. It was great to feel such peace of mind.

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
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.0 out of 5 stars
1 review
from
$30
per night

About: Personally, I was born with cats and had a multiple over my entire life! Consistently, I helped take care of six cats for 4 years, and am currently helping take care of 5 for going on 7 years! While these cats are not technically my own, I have loved taking care of them when I am home from college. I have On top of this, I have walked dogs in the past for family members and even assisted watching one as well. I am going to be working part-time come mid-December with a lot of free time on my hands! I am flexible in my schedule and looking forward to pet-sitting more! At my own home, we treat our pets with frequent, caring pets and we feed them twice a day (and more if someone missed a meal!) and make sure the water is constantly refilled! We also handle cleaning up the liter for our personal cats and cleaning up any accidents that may occur! For dog walking, I would use plastic bags to help pick up any feces.

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Chestertown House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Chestertown are rated on average 4.9 out of 5 stars based on 45 reviews.

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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.

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