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

Over 64 pet parents in Chesapeake Ranch Estates-Drum Point have booked house sitting
Chesapeake Ranch Estates-Drum Point, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“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 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.
“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!”


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 got the love of dogs from my father. I grew up on a farm and we always had a dog around. When I moved out on my own, I always had a dog from 1987-2024. For many years I had 2 dogs at a time. Since I never had children, they were my children. I 've had cocker spaniels, a rottie and a lab. I've taken care of my friends dogs when they are out of town. I currently work f/t Mon-Fri from 7am-3pm. I am only 5 miles away, so if needed, I can run home in middle of my workday for potty break and of course a mid day snack and plenty of pettings. I have a small fenced yard (I live in a townhome, end unit) Your furbaby will go on walks with me with their leach. They can sleep on the couch, in my bed, or wherever they are most comfortable.
“Spazz had some diarrhea issues but I think it was because he was missing us. Kim did an excellent job with Spazz and I'm thankful I met her back in 2022. Kim is very knowledgeable with dogs and takes her job very seriously with all of the animals she works with and I couldn't be more pleased.”

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.
“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!”


“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.”

“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!”

“I highly recommend Kathleen for anyone looking for in home or not care. Kathleen allowed us to take a wonderful holiday vacation knowing our 16 year old boy with Kidney issues would be well loved and cared for as she sent pictures daily and was always available for a checkin. Kathleen also took care of our home and eneded her stay as if she had never lived their for 10 days. Just amazing! We were pleased more than we ever thought we would be. Highly recommend this wonderful gal who we did just meet as she came 3 times prior to my trip to ease my nerves. Real gem and she and her family are great with animals. Katu was comfortable right away, which is unusual. Thank you Kathleen. You are our sitter for Katu! Happy New Year! Loved your family Christmas card! Thank you so much!”

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.
About: I’ve had different types of animals my whole life and I’ve always loved caring for them. I used to baby sit my cousin dog a lot and it would usually last a week or so. I definitely have no problem taking care of your furry friends!! Pet care fits into my daily weekly routine since I wake up early for work and get back early as well. I’m open on the weekends and I love to walk! So they will definitely get their walks in. I have a bird and he gets to come out and stretch his wings he does get feed daily along with his water being changed daily. I would definitely do the same for anyone’s pet and make sure they are taken care of and have food and water and make sure they are getting out to exercise and use the potty.
“Christina was very attentive with Mr. Moo and her pictures helped us get through the long weekend without our chunky monkey. She left our house and our cat in excellent condition and he wasnr even mad at us when we got back, which is always a giod sign that he was well taken care of! We wouldn't hesitate to work with her again.”
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.

“Ariel V. was completely wonderful. My cats were all very happy with her, even my shy guys. Ariel was very attentative to Rascal, my old guy, and he just lapped up her attention. She sent videos and updates on how everyone was doing.”

The median cost per night for house sitting in Chesapeake Ranch Estates-Drum Point is $50
Pet parents share their Rover experiences - Chesapeake Ranch Estates-Drum Point
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your pets like family

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Select a filter and find qualifying Chesapeake Ranch Estates-Drum Point sitters!Sitters in Chesapeake Ranch Estates-Drum Point average 4 repeat house sitting clients
FAQs for House Sitting - Chesapeake Ranch Estates-Drum Point
Frequently asked questions about Rover
The average cost for House Sitting in Chesapeake Ranch Estates-Drum Point on Rover is $54.39 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of July 2026, there are 308 sitters on Rover offering House Sitting across Chesapeake Ranch Estates-Drum Point. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Chesapeake Ranch Estates-Drum Point walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Chesapeake Ranch Estates-Drum Point maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Chesapeake Ranch Estates-Drum Point choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Chesapeake Ranch Estates-Drum Point. On Rover:
- 95% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 95% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.










