Pet Sitting Chesapeake Ranch Estates-Drum Point
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

Over 115 pet parents in Chesapeake Ranch Estates-Drum Point have booked pet sitting
Chesapeake Ranch Estates-Drum Point, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Hannah was wonderful with our dog. She had great communication and she also was able to come last minute when our other sitter canceled. I will definitely be requesting her again!”

“Caitlin was fantastic! I wanted to meet with her prior to booking so she could meet Ben and she came twice to do that. Ben is very timid and in foster care with me to hopefully stay. Caitlin was patient with Ben and she made him comfortable! He hid the first 2 days and then just wanted her attention and love. She gave it to him. My home was just like I left it and Ben was well cared for while I was away. I highly recommend Caitlin.”


“Riley was absolutely amazing with our bucket dog. Bucket is high energy and loves attention. Riley was timely and very tentative to buckets needs. She was very easy to comunicate with and overall will be hiring her again the next time we need some extra hands with our dog.”

About: I’m a pet parent to 4 dogs of various sizes and 1 cat, so I’m very comfortable caring for animals with different personalities, energy levels, and needs. I have 13 years of experience working with pets of all ages, including seniors and special‑needs pets with clear instructions. I work full time Monday through Friday, so my availability is 5 PM–10 PM on weekdays, with open availability on weekends. I’m happy to provide treats with your approval, and I prefer traveling to your home so your pet can stay in a familiar environment. Baths can be given upon request. I do not trim nails or hair since I’m not certified for grooming. If your pet has special routines, medications, or accommodations, I’m more than willing to follow them. Feel free to reach out anytime — I’m always happy to answer questions and help you feel confident about your pet’s care. I currently work full-time in the medical field. I’m able to provide weekend care and minor drop in and walks during the week day. I have several pets at home. If your pet does well around other animals I will be able to house them for a few days. I’m available for dog walking all weekend. Limited availability during the week.
“We had a wonderful experience with George! He was attentive, reliable, and genuinely caring throughout the entire stay. He took the time to play with and give Gyp plenty of affection and pets, which he absolutely loves! I was especially happy to see how quickly and naturally the two of them bonded. It was clear that Gyp felt comfortable and was well cared for. Communication was great, and we had peace of mind knowing Gyp was in such good hands. We are so grateful for the warmth and attention he gave Gyp. It means a lot to find someone who cares for your dog as if he were their own. We would We had a wonderful experience with our dog sitter! He was attentive, reliable, and genuinely caring throughout the entire stay. He took the time to play with and give Gyp plenty of affection and pets, which he absolutely loves! I was especially happy to see how quickly and naturally the two of them bonded. It was clear that Gyp felt comfortable and was well cared for. Communication was great, and we had peace of mind knowing our dog was in such good hands. We are so grateful for the warmth and attention he gave Gyp. It means a lot to find someone who cares for your dog as if he were their own. We would happily welcome him back anytime and would definitely book him again. Thank you for taking such wonderful care of our boy! definitely book him again. Thank you for taking such wonderful care of our boy!”


“Shemoy was great taking care of our two kitties and drop in visits! She kept us informed for each of her visits with pictures and she was always quick to respond to any messages. We will definitely have her back!”

“My cat is normally quite wary of new people, but she seemed to warm up to Tisha very quickly. Tisha also helped clean up a kitty mess which was more than I could’ve asked from her. Highly recommend!”

About: I have loved animals for as long as I can remember, and I would be honored to care for your pet friends! I currently have two sweet cats that I adore, and I frequently watch my family’s Havanese dog. I also have experience pet sitting and walking larger dogs, so I am comfortable with pets of all sizes. I have experience working with all ages, from helping with puppy and kitten training to providing gentle care to elderly pets. I tailor care to each pet’s needs, making sure they feel loved, safe, and happy while you’re away. My pets have big personalities, so I understand pets’ unique quirks and am happy to follow any special routines. Just let me know how I can help! My schedule is very flexible right now, so I have plenty of time to care for your pets! My Rover calendar is up to date with my availability, so don’t hesitate to reach out for any pet sitting, dog walking, or drop in visits. During visits, I focus on making pets feel safe and comfortable in their familiar environment. I carefully follow each pet’s routine for feeding, playtime, litter box care, or walks. I’m attentive to their behavior and needs, and I always respect my clients’ homes while providing loving, reliable care.
About: I have been taking care of animals for as long as I can remember. I have spent time volunteering at the local shelters. I have a passion when it comes to animals. I am currently a waitress serving nights. I am free during the morning and daytime hours to spend time with your animals while you’re working! I have a 2 year old daughter that will be joining me for daily walks/check ins. Please make sure your animals are okay with small children.

About: I have a golden retriever of my own, and have been dog sitting, walking and taking care of other families and friends dogs for about 5 years. I am home from college for the summer, and taking classes at night. I am available during the day and mornings, and have fairly open weekends. I have experience walking pets, feeding them, giving them medication if needed, or just spending time with them while their owners are away! I love sending photos and videos to their owners while they are away.
“Kathleen again gave us peace of mind as we went to visit family! Katu now knows Kathleen as well as she knows him. I recommend highly Kathleen as she is a natural with animals. Katu is now 17 years young!”

About: I’ve had pets since I was a kid and wanted to turn my love into my career so I started vet tech school. I work at a boarding facility so I’m no stranger to messes. I’m experienced with training young pups, senior care, and giving medications. I work part time currently, so my availability is pretty flexible and will have plenty of time to care for and play with your pets. I have an unfenced yard, but the neighborhood is about a mile one way so they’ll have plenty of space to take walks. I also live close by a dog park that we can visit if they need a little extra space to run around. I have a dog and a cat but my cat will only be limited to my room.
“Cathy has won Ranger’s heart! ❤️ Last night was the first time we ever had someone do a drop-by/night-night visit for Ranger and it could not have gone better. Cathy sent photos of their visit and when we returned home, Ranger was happy and calm (no separation anxiety behaviors as in the past). So grateful! This is the beginning of a fantastic relationship! ?????”

“Cara was great with my special needs hedgehog Ilah who needed daily oral medication as well as with my cat Nancy. She even made us a Christmas ornament from Nancy's paw print. Definitely recommend Cara and will be booking again in the future.”

“I give Bree a rating of 1000/10. This was the longest time (8 days) that we had to leave our curmudgeonly old-man behind and I was concerned, but Bree went above and beyond to make sure our Puppy Cat had companionship and felt loved. She kept in regular communication with us and reported in detail about each visit with him. She even provide photo evidence that he allowed her to touch him! I didn't think about it until I saw the pictures she provided, but she paid attention to the details during our initial meeting and I was especially pleased that our old man's food was handled how and where he was used to so it was one less disruption. We will definitely ask Bree to sit for us next time we need.”


About: I’ve had experience in pet sitting for minimum 10 years. Attention to detail and care for pets needs come first. Restrictions if any are considered as well. Morning, mid day, and evening walks are a must. As well as feeding, as frequent or less as needed. Pets will remain hydrated and have ample play time and relaxation time throughout the day. I offer a fenced yard with a seperate play area inside of home dedicated to pets. There will be ample space inside, or outside of home for pets to flourish and plenty of dog parks available if preferred.
About: I’ve had 3 dogs since I was 15 years old and have volunteered at animal shelters since college. I love animals, they warm my heart and deserve the world. I currently work remotely for a 9-5. My schedule is open during the day and have a lot of free time for dog cuddles and walks. I have a fenced in yard, I do not walk without a leash and carry a stick for any unexpected foul play from other dogs.
The median cost per visit for pet sitting in Chesapeake Ranch Estates-Drum Point is $20
Pet parents share their Rover experiences - Chesapeake Ranch Estates-Drum Point
Riley was absolutely amazing with our bucket dog. Bucket is high energy and loves attention. Riley was timely and very tentative to buckets needs. She was very easy to comunicate with and overall will be hiring her again the next time we need some extra hands with our dog.

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.

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 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.
How to book pet sitting

1. Search
Browse profiles of sitters near you who offer pet sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for pet sitting - Chesapeake Ranch Estates-Drum Point
Select a filter and find qualifying sitters offering pet sitting.Sitters in Chesapeake Ranch Estates-Drum Point average 5 repeat pet sitting clients
FAQs for Pet Sitting - Chesapeake Ranch Estates-Drum Point
Frequently asked questions about Rover
The average cost of Pet Sitting in Chesapeake Ranch Estates-Drum Point is $22 per visit as of November 2026. Most bookings cost between $0 and $31 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 523 sitters on Rover offering Pet Sitting across Chesapeake Ranch Estates-Drum Point. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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.
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.
Yes, you can find sitters who have experience with handling special pet needs in Chesapeake Ranch Estates-Drum Point. On Rover:
- 90% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 96% 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.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.












