House Sitting Chesapeake Beach
Find a loving house sitter to watch over your pets and your home.
Over 41 pet parents in Chesapeake Beach have booked house sitting
Chesapeake Beach, Find top rated house sitting
“Jamie did a wonderful job house sitting and caring for our two dobies! It's so much easier on the dogs to get to stay in their own home while we are away, and we were so grateful to find such a caring and thoughtful sitter. Jamie followed all special instructions and provided a ton of exercise and TLC. The girls have been sulking ever since she left. We would recommend her services to anyone looking for an experienced professional to care for their four-legged loved ones.”
“Michelle did a great and perfect job for our 3 doggies We come back after 1 week out of town and everything was cleaned from her , the dog's fall in love with her.We would highly recommend Michelle for other costumers…thanks again Michelle….Antje & Jens”
“Amanda took such great care of our dogs and cat. Amanda communicated lots of fun stories about their behavior and sent plenty of pictures. I'm certain my house was cleaner after her stay as well.”
About: Hello! My name is Kendal, and I’m a dedicated, dependable, and experienced pet sitter with a genuine love for animals and a strong commitment to their care and well-being. With 7 years of experience caring for dogs, cats, and other household pets, I understand how important it is to find someone you can trust to look after your furry family members. Whether it's daily walks, feeding, medication, or simply keeping your pets company while you're away, I provide attentive, personalized care to ensure your pets stay safe, happy, and relaxed. I take pride in maintaining a clean, safe environment and following your pet’s routine as closely as possible. You can expect regular updates, clear communication, and a high standard of professionalism at all times. Services Offered: ▪️Drop-in visits ▪️Dog walking ▪️Overnight care ▪️Medication administration ▪️Personalized care based on your pet’s needs Let’s connect I’d love to meet you and your pets and discuss how I can help make your time away worry-free. I’m currently working part time due to school this upcoming semester. Most of my classes are online so I spend a lot of time at home. I make frequent stops at home during the work day as I’m only 10 minutes from home to let my dogs out of my parents aren’t home. I have an electric fence however dogs would be put on leash. My cats have all their necessities in my room so the pet I would be pet sitting for would stay in the guest bedroom in the basement with me to avoid troubles.
“Cynthia was great with our dogs! We came home and they were happy and well taken care of. She sent plenty of pictures and updates. We would be happy to have a Cynthia stay with our dogs again!”
“Lindsay stayed for 10 days with my 17 year old cat. He takes many supplements and meds and Lindsay followed the schedule precisely. She sent updates and pics everyday to let me know how it was going. She made sure he was well cared for and that he felt comfortable with her. After the first day, he was snuggling with her on the couch. She checked in when she had questions. Lindsay was respectful of my home which made me very comfortable having her stay. She was an excellent sitter and I would highly recommend her. I will absolutely be rebooking with her anytime I need to go out of town.”
About: - I love dogs and will provide a large amount of love and pets for your pup - I foster dogs and cats within my community so I have multiple experiences with befriending a variety of dogs and puppies - I have administered insulin shots and ear pricking for checking blood sugar - I can administer any medications your dog may need. - I have 3 dogs of my own, a boarder collie, a Pomeranian, and a pit mix. - I have a high energy dog and can match that energy with your dogs! - I am clean and tidy and keep my surroundings as such - I have been taking care of dogs for my entire life - I have experience taking care of four large, energetic dogs in one house - I have taken care of both sick and healthy dogs, so I have the skills and knowledge to help your old or sick dogs - I love walking and running with dogs and will do either upon request - Playing with dogs is one of my favorite activities, show me your dog's favorite toys and I'll play fetch with them! - Taking care of your pup is my number one priority, always I work from home, so I can help out whenever needed! I am always available mid day to help your buddy out with a nice long walk. I have three dogs of my own, they all have seperate routines to keep up with. The high energy dogs get high energy play time with long walks, training, and kisses. The low energy dog gets nice long sniff walks followed by more kisses.
About: I have a rescue dog and I’m very aware of rescues special needs, Iv cared for all sizes of dogs and treat them like my own! Along with cats, pigs and lizards ! I have a full time job , I work four ten hour shifts I am off every Thursday and every weekend and after work hours too if needed I am willing to do morning and evening shifts on the days I work I have a open yard , If your dog needs to be crated that’s fine my dog sleeps on the couch and gets in beds
“I booked a 10 house-sitting stay with Mika and was overjoyed to see videos of my retriever mix so very happy and comfortable. I could tell my Mila loved the attention she got. My dog is 12yr old this coming July and I wanted someone with experience. Mika's vet assistant background was perfect as well as her history with rescues and special needs pets. My anxiety for such a long stay was quickly eased after the first photos and texts. Mika's upbeat attitude is refreshing. She's totally focused on Mila"s every need. I gladly recommend her. I will certainly book again. Deb”
“She gave my pups so much love, and even fed my anxious one my hand, and waited patiently for Nala to come to her. She gave them extra treats and stayed with them for long periods of time. She’s amazing!!”
About: As a proud dog mom to my own rescue pup, I know firsthand that dogs are more than just pets—they're family! 🐾❤️ I absolutely adore my dog and understand how important it is to find someone you can trust to care for your furry family member. I have a genuine love for dogs of all breeds, sizes, ages, and personalities! I also have hands-on experience volunteering at the Humane Society, where I walked and cared for dogs with a variety of temperaments, energy levels, and individual needs. In addition to providing everyday care, I have experience administering medications and giving injections, allowing me to confidently care for dogs who may require a little extra attention or have specific medical needs. I understand the importance of following instructions carefully, maintaining routines, and ensuring every pup receives safe, attentive, and compassionate care. Whether your dog needs a fun walk, a drop-in visit filled with playtime and cuddles, or a comfortable home away from home while you're traveling, I'd love to help! I understand that every dog has their own personality and needs, and I strive to make each one feel safe, happy, and loved. My goal is simple: to treat every dog as if they were my own! I would love the opportunity to care for your furry family member and provide you with peace of mind knowing they're in loving, capable hands. 🐶💕 I work from home, which allows me to have a flexible schedule and be present throughout the day to provide attentive, personalized care. My own dog gets exercise at least three times a day, whether that's going on walks, enjoying outdoor playtime, or participating in activities to keep her physically and mentally stimulated. Because I'm home throughout the day, I'm able to accommodate frequent potty breaks, feeding schedules, medication needs, and plenty of companionship. I love keeping dogs active, happy, and engaged while also making sure they have time to relax and feel comfortable. Whether your pup is staying with me or needs walks or drop-in visits, I'll treat them like part of the family and make sure they receive the same love, attention, and care that I give my own dog! My home is a welcoming, dog-friendly environment where your pup will be treated like part of the family! 🐾❤️ I have a spacious yard with plenty of room for dogs to run, play, explore, and burn off energy. I also live in a beautiful waterfront neighborhood, which provides wonderful opportunities for scenic walks and even swimming for pups who enjoy the water (with owner permission and close supervision, of course!). I have a friendly, playful rescue dog of my own who absolutely loves meeting new dogs and making furry friends! She enjoys having a playmate, and I always prioritize safe, positive introductions to ensure everyone feels comfortable. Dogs are family in my home, which means they're more than welcome on the furniture for plenty of snuggles and relaxation! I want your pup to feel just as loved and comfortable as they do in their own home. Safety is always my top priority. I always feed dogs separately to prevent food-related conflicts, and I never leave dogs together unattended, regardless of how well they get along. I carefully supervise playtime, respect each dog's individual boundaries, and provide separate spaces when needed. Since I work from home, I'm able to offer plenty of attention, frequent potty breaks, exercise, and companionship throughout the day. For walks and drop-in visits at your home, I make sure to follow your dog's established routine, including feeding schedules, exercise, medication administration, and any special instructions. I understand how important consistency is, especially when you're away! My goal is to provide a safe, fun, loving, and stress-free experience for every dog in my care while giving you complete peace of mind! 🐶💕
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.
“This is the 3rd or 4th time we have booked Vanessa! She’s amazing! She stays at our house for us. She watches our dogs and cat and she loves them like her own. I’m glad that when my wife and I go out of town we can leave without having to worry about our animals while we are gone. She’s an amazing sitter for our animals! She’s extremely attentive and very friendly! We will definitely continue booking Vanessa every time we go out of town!! It’s always a struggle to find someone who will take care of your animals the way you do, but for us, Vanessa is that person!!”
“Khadijah took amazing care of our two kitties and our home while we were away. The cats warmed up to her quickly, and she kept us updated regularly, which really helped us relax and enjoy our trip. We even had a brief wifi/electricity outage during her stay, and she handled it with total patience and flexibility. We'd absolutely trust her again for future sits and highly recommend her to anyone looking for a reliable pet sitter.”
The median cost per night for house sitting in Chesapeake Beach is $50
Pet parents share their Rover experiences - Chesapeake Beach
Rachel is so incredibly kind and easy to work with! You can tell without a doubt that your animal is safe in her care. We also got so many pictures and videos which was much needed!! She cared for our home so well when we were out of town. I will certainly be rebooking with her in the future!
Faith did an absolutely amazing job taking care of our two dogs! From the beginning, she was dependable, attentive, and genuinely caring. It was obvious that she treated our dogs like they were her own, which gave us tremendous peace of mind while we were away. Faith kept us informed, made sure both dogs were happy and well cared for, and went above and beyond what we expected. Coming home to two happy, relaxed dogs told us everything we needed to know. We completely trust Faith with our dogs and wouldn’t hesitate to have her watch them again. If you’re looking for someone who is responsible, trustworthy, and truly loves animals, we highly recommend Faith. Five stars all the way!
Anna stayed with our two older beagles (10 y/o and 12 y/o) for a few days, with the oldest beagle requiring extra assistance due to ongoing back issues. Lucy and Linus were well taken care of while we were gone, as was our house. She provided communication and pictures to keep us updated, which we appreciated! We would definitely recommend Anna!
Savanna has watched our dogs for years, sometimes on short notice like this most recent time. Another dog watcher had to cancel at the last minute and Savanna saved the day. She is the perfect dog sitter because you literally don’t have to worry about anything. She handles caring for your house and your pets as if she was a family member.
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 house sitting
1. Search
Browse profiles of sitters near you who offer house 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 house sitting - Chesapeake Beach
Select a filter and find qualifying sitters offering house sitting.Sitters in Chesapeake Beach average 4 repeat house sitting clients
FAQs for House Sitting - Chesapeake Beach
Frequently asked questions about Rover
The average cost of House Sitting in Chesapeake Beach is $50 per night as of November 2026. Most bookings cost between $34 and $113 per night. 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 4,384 sitters on Rover offering House Sitting across Chesapeake Beach. 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 Beach 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 Beach 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 Beach 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 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.
Yes, you can find sitters who have experience with handling special pet needs in Chesapeake Beach. On Rover:
- 87% of sitters can help with special care needs
- 91% can help with giving oral medications or injections
- 94% 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.
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