House Sitting in Chesapeake Ranch Estates-Drum Point
Find a loving house sitter to watch over your pets and your home.

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Top rated Chesapeake Ranch Estates-Drum Point house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I have taken care of many dogs ever since I was a kid. Personally, I have three dogs, two golden retrievers and one golden doodle. I have dog sat for friends and family with many different breeds and in different locations over the years. I am a teacher in Calvert county during the school year. After middle of June, I will be free to walk or dog sit all day everyday unless I am booked ahead of time. I have three dogs of my own so I already am used to walking dogs and taking care of them all hours of the day I have a small fenced in area and a crate where I am located. I also have easily accessible areas for walking and enjoying the outdoors. My three dogs are friendly but I am also willing to come to your house for walks, check-in’s, or dog sitting if that is preferred. I have experience with going to others houses to dog sit. For walks, I can do short walks or long walks depending on owners requests.
“Best sitter I’ve ever had. The dogs love her. She takes time to play and love on them. I recently lost my husband and she talked to me about one dog displaying severe session. Absolutely the BEST!”

“Leah is fantastic! We all know a “dog Mom” that doesn’t want to leave home because of her BABY!! (That’s me??♀️) Leah is patient and attentive, she went above and beyond for us on an extended stay. My dog, my home and my sanity were all in check with Leah. I can’t thank you enough, we will be booking again!”

“Ashley was great with my dogs! She made sure to send pictures every day to help keep us at ease that our boys were doing okay. The dogs love her and we can’t wait to book with Ashley again!”

“Juliana was a joy to work with and took thoughtful care of my home and dog! She was knowledgeable, kind, communicative, and patient with Hugo getting used to her. Upon my return, she had followed instructions thoroughly and carefully, and Hugo was well cared for and happy. And so am I! Thank you, Juliana!”


“Shemoy was wonderful! We have had bad experiences with Rover dog sitters in the past, but she made us feel very at ease while watching our dog. She was very responsive and reliable. She even left the sweetest Christmas treats for my dog. You can tell she really cares about animals. I will definitely book with her again.”

“Samuel did a fantastic job watching our dog who is both quite reactive and recovering from ACL surgery. We already rebooked him for next month and highly recommend him for anyone needing peace of mind while they’re away from their fur baby.”


“Elizabeth was attentive to Daisy's needs per the 'care & feeding' instructions we provided. Just as importantly, she treated Daisy as if her own, which was apparent by Daisy snoozling on Betsy's luggage as she prepared to leave.”


About: I’ve cared for pets for several years & genuinely love spending time with animals. I have experience feeding, walking, playing with, & giving attention to dogs & cats of different sizes & personalities. I’m reliable, patient, & always make sure pets feel loved & happy! I have a flexible schedule & enjoy making time for pet care throughout my week. I’m available for walks, playtime, & I make sure every pet gets plenty of attention. I make sure all pets get exercise & care, I’m dependable, commutative, & will always do my best work. I will make sure I work to your pet’s routine & needs. I provide a safe, loving, & comfortable environment for every pet in my care. I pay close attention to each pet’s needs, routines, & personality to help them feel relaxed & secure. I can follow feeding schedules, give plenty of playtime & potty breaks, along with putting them in a crate if needed. My goal is to make pets & owners feel comfortable as much as possible.

About: Hi there! My name is Hannah, and I’ve been around animals my entire life. I’ve cared for dogs, cats, and other pets, so being around animals feels completely natural to me. I also have hands-on experience working at Interlude Pet Resort & Spa, where I helped care for dogs of all sizes and temperaments. This included feeding, cleaning, walking, and making sure each dog felt safe and comfortable. In addition, I’ve provided pet sitting and dog walking for friends, family, and family friends. I understand how important it is to keep pets on their normal routine and give them the attention and care they’re used to. I’m very patient, reliable, and genuinely love spending time with animals. Whether your pet is energetic, shy, or needs a little extra attention, I’ll make sure they feel safe and cared for. I’m also happy to send updates and photos so you always know your pet is doing well while you’re away! I’m currently not working so i’m available all days of the week! 9:00am - 11:00pm all days of the week! I also would never pass up the opportunity to love on your fur baby! I’m used to scheduled feed times and walking bigger and smaller dogs. I like to go outside and throw a ball/frisbee or any other toy that can be used to get some exercise in.
“Kristen was absolutely wonderful with my Pomeranian mix, Jasper, over Spring break. From the very beginning, she was flexible with my schedule and made the whole handoff seamless and stress-free. It was clear she genuinely cared about Jasper’s comfort and wellbeing. She was attentive, communicative, and completely dedicated to making sure he was happy and well looked after while I was away. Knowing Jasper was in such good hands allowed me to fully enjoy my time away without a second of worry. I couldn’t have asked for a better sitter. I will absolutely be reaching out to Kristen again and recommend her without any hesitation!”

About: I am a responsible and dependable college student who genuinely enjoys caring for animals. I understand that every pet has their own personality, routine, and needs, and I take the time to make sure they feel comfortable, safe, and well cared for while you're away. I am attentive to feeding schedules, exercise needs, medications, and any special instructions provided by owners. I also believe in keeping pet parents updated with regular messages and photos so they can have peace of mind while their pets are in my care. In my own personal experience I have worked with pets ever since I was 13 and have loved animals my whole life. I have watched multiple animals at one time, administered medication, provided walks, provided cuddles/play times, and provided over night stays for the past few years. Whether your pet enjoys long walks, playtime, or simply having a calm companion around, I will provide patient and loving care tailored to their needs. My goal is to treat every pet as if they were my own and ensure they receive plenty of attention, affection, and care. I am currently working a part-time internship related to my major for school. This internship only takes up 15 hours of my time during the week. I am available to play and care for your pets any time during the weekend and when I am not working. As I do not have my schedule yet, I estimate most of my time will be spent with your pets in the evening during the week and whenever we can make work! I am very flexible. Safety and comfort are my top priorities when caring for pets. In a client's home, I follow all care instructions carefully, including feeding schedules, medication routines, exercise needs, and any household rules. I make sure pets have fresh water, a clean environment, and plenty of attention and companionship while their owners are away. I understand that pets are often most comfortable in their familiar surroundings, so I work to maintain their normal routine and minimize stress. I also pay close attention to any changes in behavior or health and will communicate promptly with owners if I have any concerns. I treat every home and pet with respect, keeping living areas clean, securing doors and gates, and ensuring pets remain safe at all times. I provide regular updates and photos so owners can have peace of mind knowing their pets are happy, comfortable, and well cared for.
About: I have fur babysitting experience over the past year. I understand what it’s like to have to put your full and undivided attention into a child to ensure its safety and well being, and do nothing different with the pets I take care of. They will be no need to worry when I’m taking care of them. Currently working part time and in school at CSM. Can be very flexible with scheduling to ensure the pets get the proper love and affection that they deserve and need. I give the pets constant love so that they don’t feel down when their owner isn’t home. I understand that pets can feel sad or get into a rut when their parents are not home, but I will do everything to make sure they feel nothing but love. I send lots of photos so you will feel connected while away.

“I contacted India on relatively short notice for pet sitting. She was available to come meet us and our dog before our trip. India did a wonderful job taking care of our older German Shepherd who is dealing with some skin conditions. She was very caring and followed all of the instructions that I left for medicine and wound care. We appreciate the care that she gave our girl and will definitely book with India again to take care of our dog. We also have a bearded dragon and fish that she took care of as well. Highly recommend India for pet sitting.”


About: I’ve had animas my entire life from dogs to chickens, rabbits, a chinchilla, turtles, a bearded dragon, cats, and more! Dogs hold a special place in my heart. I’ve trained with dogs my whole life. I worked at a dog kennel for 7 years, trained dogs professionally for 4, and recently graduated from an accredited dog training school called Starmark! I have also been trusted and recommended by many people who know me well and they have all given nothing but good feedback and compliments, I take pride in my animal care! I am currently between jobs after graduating and so I have a lot of free time to dedicate towards helping people and animals! You may message me with any further inquiries or questions you might have! While I do not have a fenced in yard, I am still very capable of providing lots of enrichment for dogs! My dogs go to parks, they walk on long lines outside to give them a lot of space, we go on sniffy walks, they get lick mats, enrichment toys, mental games, training, and so much more! My yard is also very large featuring a large in ground pool (fenced in) and multiple large areas of grass and lots of woods behind my house! I also have chickens that while kept in a secure, separate area, help keep the tick population minimal!
About: Hi! I’m Rosie — a lifelong animal lover and rescue-pet mom to one sweet pup and two cats. I’ve had pets since childhood and have always been drawn to helping animals who need a little extra love. I volunteer with a local shelter to support dog and cat socialization, and I also work with an island-dog rescue that brings pups from Puerto Rico to find their forever homes in the U.S. Whether it’s walks, playtime, or quiet company, I’m here to make your pet feel safe, loved, and well-cared for while you’re away. Pet care fits easily into my routine. I’m available early mornings, late afternoons, and evenings, with flexible weekends to ensure your pets get consistent, loving attention. In my home or yours, I focus on routines that build confidence and trust. I use gentle reinforcement, reward-based training, and plenty of love, cuddles, and playtime to help pets feel secure.

About: I’ve had dogs my whole life and have been taking care of them since I was a kid! I have two dogs and a cat of my own who are family! So I understand how important it is to trust someone with your pets! Im currently a stay at home mom and wife I have plenty of time to walk, play and cuddle your fur baby’s! Any time of day or night I can be there for you and your family I can take you dogs for a walk around the neighborhood or around your yard! I am comfortable putting them in crates and feeding or any type of play what ever you need I can do!
About: I absolutely love all animals!! I have a Beagle that is great with other dogs and children! I work from home and have a large fenced yard that dogs love! I am ready and available to host your pups for overnight needs or come walk your dog(s) so that you can focus on other needs! If I host your dog overnight, I prefer a housetrained pup but am flexible with that. Expect lots of pictures while your furry family member is here ! I work from home so will be home throughout the day, with the exception of short errands runs. If your pupper needs a crate, please feel free to bring one! Large fenced yard for lots of outdoor time. I have dog beds throughout the house for sleeping, and dogs beds outside for lounging and sunbathing!
“Kathleen is amazing! She checked in regularly with pictures of my relaxed and content baby. She was caring and attentive. She even picked up on his silent cues for when he wanted a snack or treat. When we came home, it was as if we'd only been away for 10 minutes. There is no one I'd trust more.”

Chesapeake Ranch Estates-Drum Point pet parents share their Rover experiences
How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. 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 away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Chesapeake Ranch Estates-Drum Point is $50
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.
Sitters in Chesapeake Ranch Estates-Drum Point average 4 repeat house sitting clients
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 Chesapeake Ranch Estates-Drum Point on Rover as of Jun 2026 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.
If you’re searching for a Chesapeake Ranch Estates-Drum Point house sitter for the first time, visit the house sitter’s profile and select the Contact button.
If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.
As of Jun 2026, there are 219 house sitters in Chesapeake Ranch Estates-Drum Point. 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, 87% of Chesapeake Ranch Estates-Drum Point house sitters respond in under an hour.
House sitters in Chesapeake Ranch Estates-Drum Point have an average of 14 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 Chesapeake Ranch Estates-Drum Point.
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. Chesapeake Ranch Estates-Drum Point 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.





