House Sitting in Chestertown
Find a loving house sitter to watch over your pets and your home.

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Top rated Chestertown house sitters

“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.”


“Jamie stayed with our boy for a week. We haven’t been away from him in two years He sent multiple pictures each day. We came home to find Mika relaxed and not stressed of going to a boarding facility. Jamie also brought in our garbage cans and mail to give our house a lived in feel when away. Highly recommend and will use him again!”


“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!”


“When we were planning a trip out of the country, we wanted someone who was serious and committed to doing the best job they could for our cats and our house. We found this in Michael, who quickly earned the love and trust of Bagheera & Laska, our 2 cats. They are so different in personality and temperament it's hard to believe. Michael quickly won over the shy, cautious Laska, and became Bagheera's best buddy for playing and walks around the yard. He's not a snuggly cat, but he trusted Michael enough to even sit in his lap. We also felt that we could completely rely on Michael to do anything that was needed. When we got back, the plants had been watered, the house was as we left it (messy but clean), and the cats were happy. We trust Michael and highly recommend him.”


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.

“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! :)”


“We loved Tre! From the minute he pulled into the driveway, we felt comfortable that he would be a great fit to care for our enthusiastic pittie mix. He asked pertinent questions and took detailed notes during the meet and greet. Our dog responded so favorably to him and the became fast friends. We highly recommend him and will definitely be working together in the future.”


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 😊

“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!”


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.

“This was our first time using Savannah. Our pup seemed happy in all the pics she sent! It’s nice to have someone close by that can check in on Ruger when my husband and I have long days away! We will definitely be utilizing her again soon!”


About: Since I was little at home we have always had pets such as rabbits, birds, hamsters, cats, dogs, fish, I have always loved animals all my life and my parents always let me take care of them under their supervision until I grew up and I was able to take care of them on my own, I began to take care of dogs and cats as a job from every summer when I was in high school, I have also volunteered in dog and cat shelters. Boarding 24 hrs Drop off 9:00 am -9:00pm Pick up 9:00 am- 9:00 pm I’m currently working from home, my job is very flexible so that give the chance to always take them out, I live close to a golf course and it has trails around, where I take my dog, there is plenty of places to take them to play, and run around. I can do weekday and weekends I’m always at home, actually my dog doesn’t know what is to be alone. I live in an apartment, they can be anywhere in my place, if your dog/cat likes to sleep with you he is welcome as well in my bed , I have a friendly 9 years old Pomeranian who doesn’t bark at all, who respect others animals space like cats and other dogs,she is really good with other animales in general.

“Marissa was awesome! Thank you so much for watching our two pups!”


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! 😊”


“Attentive, patient and communicative during our house sitting booking. Would book again!”


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: 🐾In-Home Pet Care! 🐾 Hello pet parents! My name is Brianna Cummings and I'm excited to offer professional pet sitting services right in the comfort of your own home. With a deep love for animals and a commitment to excellence, I offer comprehensive care tailored to meet the unique needs of your furry family members. 🏠 About Me: As a dedicated pet lover, I understand the importance of maintaining your pet's routine and environment while you're away. Whether you're heading out of town for work or going on vacation, you can trust me to keep your furry friends happy, healthy, and well-loved in the familiar surroundings of their own home. 🐾 Services Offered: * Feeding & Watering: I'll make sure your pets are well-fed and hydrated according to their usual schedule, including any special dietary requirements they may have. * Dog Walking & Exercise: Your pups will enjoy plenty of outdoor adventures, whether it's a leisurely stroll around the neighborhood or an energetic romp in the backyard. * Playtime & Enrichment: From interactive games to cuddle sessions, I'll provide plenty of mental and physical stimulation to keep your pets entertained and engaged. * Medication Administration: If your pet requires medication, I'm experienced in administering oral medications, injections, and other treatments as directed by you or your veterinarian. 📸 Regular Updates: I know how important it is to stay connected with your pets while you're away, (I know from my experience) so I'll send you regular photo and video updates to keep you informed on all the fun we're having together. 🤝 Meet & Greet: Before booking, I'd love to schedule a meet and greet to get acquainted with you and your pets. It's a great opportunity for us to discuss your pet's routines, preferences, and any special instructions you'd like me to follow. 🔒 Trust & Security: You can rest easy knowing that your home and pets are in good hands. I'm committed to maintaining the highest standards of care and professionalism, ensuring a safe and stress-free experience for both you and your furry family members. And please Don't never hesitate to reach out if you have any questions or would like to schedule pet sitting services for your beloved companions. I can't wait to meet you and your pets! My schedule allows for pet care on weekdays after 3 PM and flexible availability on weekends. I prioritize scheduling pet care activities, such as feeding, walking, and playtime, around these times to ensure consistency and meet the needs of each pet. This structured approach ensures that pets receive the attention and care they deserve, while also accommodating the client's preferences and schedule. Ensuring safety, trust, and a comfortable environment for pets in a client's home is paramount. I prioritize familiarizing myself with the pet's routine, preferences, and any special needs. This includes following feeding schedules, administering medications if necessary, and providing ample exercise and playtime. I maintain a clean and hazard-free environment, securing doors and gates to prevent escapes and removing any potential dangers. Regular communication with the client helps build trust, as I provide updates on their pet's well-being and address any concerns promptly. Additionally, I respect the client's home by adhering to their rules and maintaining confidentiality. Overall, my goal is to create a secure and nurturing atmosphere where pets feel happy and loved in their own environment.

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!

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.
Loving house sitters in your neighborhood
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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

“Jamie stayed with our boy for a week. We haven’t been away from him in two years He sent multiple pictures each day. We came home to find Mika relaxed and not stressed of going to a boarding facility. Jamie also brought in our garbage cans and mail to give our house a lived in feel when away. Highly recommend and will use him again!”


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!”


Michael P.


“When we were planning a trip out of the country, we wanted someone who was serious and committed to doing the best job they could for our cats and our house. We found this in Michael, who quickly earned the love and trust of Bagheera & Laska, our 2 cats. They are so different in personality and temperament it's hard to believe. Michael quickly won over the shy, cautious Laska, and became Bagheera's best buddy for playing and walks around the yard. He's not a snuggly cat, but he trusted Michael enough to even sit in his lap. We also felt that we could completely rely on Michael to do anything that was needed. When we got back, the plants had been watered, the house was as we left it (messy but clean), and the cats were happy. We trust Michael and highly recommend him.”


Elexis M.
“Elexis took excellent care of my dog. She made sure they would go out when my dogs gave notice to needing to go out. She played with them and made sure to update me when I asked.”


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! :)”


Tre S.

“We loved Tre! From the minute he pulled into the driveway, we felt comfortable that he would be a great fit to care for our enthusiastic pittie mix. He asked pertinent questions and took detailed notes during the meet and greet. Our dog responded so favorably to him and the became fast friends. We highly recommend him and will definitely be working together in the future.”


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).”


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!”


Nija H.
“I had a family emergency out of state and needed someone to sit with my furry family member, Beemer. I used Nija to walk him previously and she told me if I ever needed a sitter, let her know. I called her frantic and she was accommodating to my request! I gave her the option to stay at my apartment or take him to her home; she opted to take him to hers. Throughout the week I was away, Nija sent me random pictures and short videos of Beemer playing, resting and simply just having fun being away. She said at first he seemed anxious but after a few hours, he seemed more relaxed and played with her doggie. We have used Nija's services on a frequent basis and she is a trust worthy person with my precious little one!”


Savannah D.

“This was our first time using Savannah. Our pup seemed happy in all the pics she sent! It’s nice to have someone close by that can check in on Ruger when my husband and I have long days away! We will definitely be utilizing her again soon!”


Alina R.
“Alina is always great with the dogs and they are always so excited to see her. She is so kind and helpful, anyone needing a sitter can trust they are in good hands.”


Marissa F.Star Sitter

“Marissa was awesome! Thank you so much for watching our two pups!”


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.


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! 😊”


maranda c.

“Attentive, patient and communicative during our house sitting booking. Would book again!”


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.


brianna c.
About: 🐾In-Home Pet Care! 🐾 Hello pet parents! My name is Brianna Cummings and I'm excited to offer professional pet sitting services right in the comfort of your own home. With a deep love for animals and a commitment to excellence, I offer comprehensive care tailored to meet the unique needs of your furry family members. 🏠 About Me: As a dedicated pet lover, I understand the importance of maintaining your pet's routine and environment while you're away. Whether you're heading out of town for work or going on vacation, you can trust me to keep your furry friends happy, healthy, and well-loved in the familiar surroundings of their own home. 🐾 Services Offered: * Feeding & Watering: I'll make sure your pets are well-fed and hydrated according to their usual schedule, including any special dietary requirements they may have. * Dog Walking & Exercise: Your pups will enjoy plenty of outdoor adventures, whether it's a leisurely stroll around the neighborhood or an energetic romp in the backyard. * Playtime & Enrichment: From interactive games to cuddle sessions, I'll provide plenty of mental and physical stimulation to keep your pets entertained and engaged. * Medication Administration: If your pet requires medication, I'm experienced in administering oral medications, injections, and other treatments as directed by you or your veterinarian. 📸 Regular Updates: I know how important it is to stay connected with your pets while you're away, (I know from my experience) so I'll send you regular photo and video updates to keep you informed on all the fun we're having together. 🤝 Meet & Greet: Before booking, I'd love to schedule a meet and greet to get acquainted with you and your pets. It's a great opportunity for us to discuss your pet's routines, preferences, and any special instructions you'd like me to follow. 🔒 Trust & Security: You can rest easy knowing that your home and pets are in good hands. I'm committed to maintaining the highest standards of care and professionalism, ensuring a safe and stress-free experience for both you and your furry family members. And please Don't never hesitate to reach out if you have any questions or would like to schedule pet sitting services for your beloved companions. I can't wait to meet you and your pets! My schedule allows for pet care on weekdays after 3 PM and flexible availability on weekends. I prioritize scheduling pet care activities, such as feeding, walking, and playtime, around these times to ensure consistency and meet the needs of each pet. This structured approach ensures that pets receive the attention and care they deserve, while also accommodating the client's preferences and schedule. Ensuring safety, trust, and a comfortable environment for pets in a client's home is paramount. I prioritize familiarizing myself with the pet's routine, preferences, and any special needs. This includes following feeding schedules, administering medications if necessary, and providing ample exercise and playtime. I maintain a clean and hazard-free environment, securing doors and gates to prevent escapes and removing any potential dangers. Regular communication with the client helps build trust, as I provide updates on their pet's well-being and address any concerns promptly. Additionally, I respect the client's home by adhering to their rules and maintaining confidentiality. Overall, my goal is to create a secure and nurturing atmosphere where pets feel happy and loved in their own environment.


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.”


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.
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 Jul 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 Jul 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, 91% 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 3 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.
