House Sitting in Chestertown
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Top rated Chestertown house sitters

“Karen was great with our four animals (dogs and cats)! Karen was communicative, provided great updates, and let us know when one of our cats was having a minor potential health issue. Would recommend and I know our pets are already looking towards when Karen will be back to see them again!”

“Jaime took very good care of our three cats and home. He shared images regularly to let us know our fur babies were doing well. Usually when we go away for a few days, our cats will be stressed and aloof when we return. Not this time! All three were relaxed and we could tell they were comfortable with Jaime and he kept them on their routine feedings and care. So happy to have found Jaime on Rover.com!”


About: I'm currently training for a marathon so I love running in the park frequently. If your dog is super energetic, I would love to run with him/her to tire them out so that they will be calmer at home. Back when I had my dog Archie, I would run with him everyday so that he would sleep well at night. I've also had experience with training puppies such as potty training and simple commands. I'm patient when it comes to training. I'm currently a WFH software engineer so I have plenty of time to make sure your dog gets all the attention he/she needs! I am currently a WFH software engineer so I can take care of your dog basically anytime provided a day or two notice in advance. I have a big backyard which would allow your dog plenty of space to run around. I also do have a couple of younger cousins who love dogs too and they are willing to also help make sure your dog gets all the attention that he/she needs.

“Michael was great with our 2 large and energetic dogs (65 and 105lbs)! They felt right at home with him while we were away. Our one dog can be a bit nervous in general but they got along great. Michael has a calm and positive energy which was perfect for our dogs. We appreciated his daily updates and clear communication. He was very professional and we would definitely hire him again. He took great care of them and you can tell he truly enjoys working with the dogs. Thanks again Michael!”


About: I have experience taking care of cats and dogs going back to my early teens. I’m just as much a cat lover as I am a dog lover and would love to take care of your fur babies. Whether you have a sweet big dog or a little shy cat, I love them all the same. Most of my family has at-least 2 or more cats or dogs and they often rely on me to take care of them when they go on vacation, have a long work week, or just need a helping hand. I currently work full time, 9-5 Monday through Friday. Most of my availability is on the weekends or late afternoons. But depending on the request I may be able to make an exception. I have experience caring for small dogs, big dogs, shy cats, energetic cats, senior dogs and cats. I’ve cared for almost every type of pet there is. I’ve even cared for reptiles and guinea pigs. Whether your pet would like space and quiet or someone to help them get their energy out I can provide that. I can meet the needs of your pet. Every dog/cat is different and I’m here for it all 😊

About: I’ve taken care of many animals throughout my teen to adult years. I volunteered at a rescue taking care of mostly the cats. I’ve previously helped rescue kittens and dogs. I’ve always had animals around me. I’m a very big animal lover. I currently have 2 cats and 2 dogs and cat sit a kitten from time to time. I give the cats baths maybe once a month and the dogs weekly and I routinely walk the dogs. I watch the dogs while they’re outside while also giving them extra love. I love taking dogs on walks. I play with cats and even bring along toys that I know my cats love.

“Ashley is a wonderful dog and house sitter! She took great care of Sadie for a week while we were out of town. She did everything I requested and was always very kind and courteous. The house looked exactly how we left it. Not a thing out of place. She is very trustworthy and highly dependable. I would recommend her to anyone!”


“Brina took great care of our 10 y/o boxer when housesitting recently! She kept us informed and up to date. She took him on his favorite walk everyday and he seemed to be his fun, goofy self with her. Highly recommended!”


“Courtney was an amazing help with sitting Maxwell today. She was punctual, early in fact ;), followed all requests and most of all, made sure Maxwell was in good company. Communication was great and I felt confident that my little man would be in great care with her! We will be looking to have Courtney back in the future for sure. Thanks!”


About: I've watched and taken care of dogs for many years, mainly family and near by neighbors. I have grew up on a farm which i've taken care of many other animals as well... mainly farm animals and dogs!! I'm currently in college right now, it's mostly online so that's not really an issue. I'm working part time as well, which I have plenty of time to take care of the dogs!! I'm always free on weekends unless otherwise noted!! I have two golden-doodles, which are crate trained. They are allowed to run freely outside but they know where they are and aren't allowed. I keep them on a schedule, meaning with going outside, playing, and feeding.

About: As a passionate animal lover & dog owner, I am dedicated to providing care, exercise & fun. My goal is to ensure every walk or visit makes your pet feel just as loved as they do with their owner. Safety is always my top priority and I will treat your pet as if they are my own ensuring when you return home they will be just as happy and healthy as they were when you left. I currently have open availability including early mornings, evenings, weekends or weekdays and holidays. Please advise which schedule is best for you and your pet. Safety is always my main concern and I can assure you I will keep a close eye on your pet and advise you of any emergencies.

“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! :)”


About: I grew up with dogs and I have my own pup now. For the past 2.5 years I have worked in a doggy daycare and boarding facility. I have experience handling dogs of all sizes in groups up to 35 at a time. During the week my job is very flexible with work from home hours. I work weekends at a doggy daycare and I can bring dogs there that I’m watching or work around that schedule. I can stay in the clients home for a few hours each day for attention and playtime and I can come by for feedings and walks. My apartment is dog friendly and I’m open to boarding smaller dogs there. I have a golden retriever who loves other dogs.

“Madison did an excellent job taking care of our 12 year old St.Bernard/Staffy mix, Charm! Madison was very capable, patient, kind and moved at Charm’s pace, making Charm very comfortable with her. Madison provided great communication during her service so we were worry-free during our trip! Will rebook with Madison in the future! 😊”


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 all animals and I have family members of my own. Plus I have a little helper who isn't scared of anything and loves to help her momma as much as she can. I'm will to do what ever it takes to make sure everyone is a happy camper and provide the best care I can to keep your mind at ease knowing you family is in good hands. Feel free to ask me anything and if you have any special requests let me know I will do what I can to make it happen. I'll treat your kids as if they were my own. I'm currently employed part-time but I'm looking to get out of the retail business and starting my own pet sitting business where I can enjoy doing what I love. I currently live in a small apartment, so it ideal that I travel back and forth from my house to clients home. I have fur babies and a family of my own, hopefully when I get a home of my own I could introduce the doggy daycare and pet sitting at my home.

About: Skillful pet caregiver for your fur baby. I’ve taken care of pets and have had a love for animals my entire life. Friends and family know that they can rely on me to love, socialize, walk, feed and bathe their pets. I work a very flexible schedule which allows me to have control of my schedule therefore I’m able to be super flexible with the hours that I choose to care for your pet(s). Pets are under my supervision at all times. If needed I’m also able to crate your pet as well. When going on walks all pets will be securely leashed.

About: I have loved animals since I was a little girl! I have many years of experience with dogs, cats and even small animals like hamsters, turtles and fish. I want to be there for you, and your furbaby so you can fully relax on that vacation you have been looking forward too! I am currently employee at Washington College with a pretty loose schedule! Being able to choose my hours and be able to work around yours is 100% a possibility that sets me apart! I live in an apartment with a fenced in backyard. I live in downtown chestertown which is open to all different types of walking opportunities and is a short walk to many fields at the college!
Loving house sitters in your neighborhood
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Ahniya I.

“Ahniya was wonderful to have over and sit Maxwell. She was on time, sent updates throughout her stay and kept Maxwell entertained. Really appreciate her help!”


Karen R.
“Karen was great with our four animals (dogs and cats)! Karen was communicative, provided great updates, and let us know when one of our cats was having a minor potential health issue. Would recommend and I know our pets are already looking towards when Karen will be back to see them again!”


Chantel B.

“Chantel has great communication skills and left my home just how I left it. I really felt like my puppy was taken care of. Will be booking again.”


Jaime A.Star Sitter

“Jaime took very good care of our three cats and home. He shared images regularly to let us know our fur babies were doing well. Usually when we go away for a few days, our cats will be stressed and aloof when we return. Not this time! All three were relaxed and we could tell they were comfortable with Jaime and he kept them on their routine feedings and care. So happy to have found Jaime on Rover.com!”


Steven C.
“Steven was a huge help when my little dog slipped her leash and made a run for the crosswalk. He was able to grab her quickly despite her trying to wiggle away. He also stayed calm during the whole incident! (unlike me, lol)”


Michael P.


“Michael was great with our 2 large and energetic dogs (65 and 105lbs)! They felt right at home with him while we were away. Our one dog can be a bit nervous in general but they got along great. Michael has a calm and positive energy which was perfect for our dogs. We appreciated his daily updates and clear communication. He was very professional and we would definitely hire him again. He took great care of them and you can tell he truly enjoys working with the dogs. Thanks again Michael!”


Payton W.
“Payton is the best! If you are looking for someone who will go out of their way to make sure your pets needs are met and give you the comfort of great communication, she is your girl! She goes above and beyond putting herself in your shoes. She is easy to work with and very detail oriented, not to mention her great personality. She has taken care of all of my babies (3 cats and my new puppy).”


Elexis M.
“She made sure to take my dog out and would actively keep me updated on how my animals were doing. Was very attentive to my dogs needs.”


Ashley C.

“Ashley is a wonderful dog and house sitter! She took great care of Sadie for a week while we were out of town. She did everything I requested and was always very kind and courteous. The house looked exactly how we left it. Not a thing out of place. She is very trustworthy and highly dependable. I would recommend her to anyone!”


Brina B.

“Brina took great care of our 10 y/o boxer when housesitting recently! She kept us informed and up to date. She took him on his favorite walk everyday and he seemed to be his fun, goofy self with her. Highly recommended!”


Courtney W.

“Courtney was an amazing help with sitting Maxwell today. She was punctual, early in fact ;), followed all requests and most of all, made sure Maxwell was in good company. Communication was great and I felt confident that my little man would be in great care with her! We will be looking to have Courtney back in the future for sure. Thanks!”


Olivia B.
“Olivia always has been a dog lover . She would be very caring and respectful for any pet . She is also a responsible young lady.”


Nija H.
“Nija was Amazing , she was on time , followed all of our directions. She very much exceeded our expectations ! I will most definitely be using her again . If you need someone reliable , trustworthy and a great pet caregiver Nija is exactly that . Our dogs can sometimes be a handful but she showed that was not an obstacle she couldn’t overcome . It’s such a relief knowing i can have someone to step in when we need it the most! Thank you Nija”


Sabrina G.

“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! :)”


Shaun C.
About: I grew up with dogs and I have my own pup now. For the past 2.5 years I have worked in a doggy daycare and boarding facility. I have experience handling dogs of all sizes in groups up to 35 at a time. During the week my job is very flexible with work from home hours. I work weekends at a doggy daycare and I can bring dogs there that I’m watching or work around that schedule. I can stay in the clients home for a few hours each day for attention and playtime and I can come by for feedings and walks. My apartment is dog friendly and I’m open to boarding smaller dogs there. I have a golden retriever who loves other dogs.


Marissa F.Star Sitter

“Marissa took care of both dogs and the house while I had to travel for a week. I appreciate her care and thoughtfulness. I didn't worry at all.”


Madison M.

“Madison did an excellent job taking care of our 12 year old St.Bernard/Staffy mix, Charm! Madison was very capable, patient, kind and moved at Charm’s pace, making Charm very comfortable with her. Madison provided great communication during her service so we were worry-free during our trip! Will rebook with Madison in the future! 😊”


Cynthia R.
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 all animals and I have family members of my own. Plus I have a little helper who isn't scared of anything and loves to help her momma as much as she can. I'm will to do what ever it takes to make sure everyone is a happy camper and provide the best care I can to keep your mind at ease knowing you family is in good hands. Feel free to ask me anything and if you have any special requests let me know I will do what I can to make it happen. I'll treat your kids as if they were my own. I'm currently employed part-time but I'm looking to get out of the retail business and starting my own pet sitting business where I can enjoy doing what I love. I currently live in a small apartment, so it ideal that I travel back and forth from my house to clients home. I have fur babies and a family of my own, hopefully when I get a home of my own I could introduce the doggy daycare and pet sitting at my home.


Kashya J.
About: Skillful pet caregiver for your fur baby. I’ve taken care of pets and have had a love for animals my entire life. Friends and family know that they can rely on me to love, socialize, walk, feed and bathe their pets. I work a very flexible schedule which allows me to have control of my schedule therefore I’m able to be super flexible with the hours that I choose to care for your pet(s). Pets are under my supervision at all times. If needed I’m also able to crate your pet as well. When going on walks all pets will be securely leashed.


Gillian H.
“Gillian is amazing!! I was so happy to find out that she joined Rover. Gillian watched our dogs in Virginia and has moved to Maryland. She is reliable, trustworthy, and excellent communicator. She has given us much-needed peace of mind when we are away from our dogs. She house sat for us and it was great having the dogs in their own environment. I highly recommend her.”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chestertown on Rover as of Aug 2025 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Aug 2025, there are 374 house sitters in Chestertown. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 90% of Chestertown house sitters respond in under an hour.
House sitters in Chestertown have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Chestertown.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chestertown house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
