House Sitting Chesapeake Beach
Find a loving house sitter to watch over your pets and your home.
Over 38 pet parents in Chesapeake Beach have booked house sitting
Chesapeake Beach, 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.
“Faith is a fantastic petsitter! We were out of town for 8 days and didn't have to worry about a thing back home. It was wonderful to find a caring person who could spend this much time with our pets. Boarding can be so stressful on our big dogs, but Faith was able to do overnights and wasn't intimidated by our Dobermans in the slightest. She was a perfect fit, and we were so blessed to find her on Rover. It was our first experience with the service platform being new to Southern Maryland, but we will be repeat customers for sure.”
About: Dogs have always been a huge part of my life. Growing up with dogs taught me exactly how to read their body language and give them the care, attention, and love they deserve. I treat every furry guest just like my own, making sure they stay happy, active, and fully comfortable while you're away I’m currently working a full-time job, but I work remotely every other week which gives me some spare time and I’d love to use it to spend with some dogs. I do have two kids ages three and eight both love dogs. I don’t have any dogs in my own, but I plan to get one and then your future however I was in our home with four dogs at a time
“We booked Rose when looking for a house sitter for one night at the last minute. Our dogs seemed to take to Rose very quickly and when we returned home it seemed like we hadn't left, which is exactly what we wanted! Rose was kind and professional and sent us multiple photos of our dogs during the trip. There were also no issues at all with our house as everything seemed just as it was when we left. Highly recommend!”
“We greatly appreciate Ashley taking such wonderful care of our dogs! She kept us updated with lots of pictures and communicated well throughout the entire stay. Our house was left in great condition, and we could tell our dogs were in excellent hands. We would definitely use Ashley again and highly recommend her to anyone looking for a responsible and caring pet sitter. The dogs look forward to having her care for them again soon!”
About: I have 5 years of experience working at a kennel as a kennel technician. In this position I worked with all different breeds and ages of dogs. I learned how to take care of dogs with all sorts of health needs depending on their abilities and conditions. I have no problem with any dogs and I love working with them! I'm working a full time job but I am able to do overnight on weekends (thursday through Monday since I work from home sometimes) and I can yelp out throughout the week after normal work hours. I am comfortable with whatever specific needs your dog has. I have no problem crating a dog, walking a dog, hanging out, whatever is needed for your specific pet, I am willing and able to do.
“Liz was an awesome pet sitter. She provided daily updates and photos and asked for information when a possible concern arose. My two dogs came home well cared for and happy!”
About: I provide loving care for pets of all ages, from playful puppies to seniors, with experience in training, special needs, and making every animal feel safe. As a retiree, my days revolve entirely around the animals in my care. They receive my full attention, love, and time—morning to night, every single day. I live in a safe, animal-friendly waterfront neighborhood with very few cars and plenty of space to play. Pets enjoy walks to nearby parks and, for water-loving “babies,” splashing adventures at the bay—all in a calm, welcoming environment where they’re treated like family.
“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”
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
About: 15+ years of rescue work and fostering dogs/cats. Over 1000+ Fosters and boarders. Experience with all different ages, breeds, medical issues. Able to handle a large pack and individual needs I have flexible hours and can be there for all your pets needs on a case by case basis. I have a very structured routine. Safety is key, walking the property daily to ensure no escape routes and doing door/window checks to keep everyone safe. Keeping their routine as close to normal as possible is key to happy pets.
About: I provide dependable, attentive care for both dogs and cats, making sure each pet feels safe and comfortable while you’re away. I’m experienced with different personalities, from energetic and playful to calm or shy, and I adjust my care to fit their needs. I handle feeding, walks, litter cleaning, and playtime while sticking closely to your pet’s routine. I’m responsible, observant, and genuinely enjoy caring for animals, which helps me build trust quickly with every pet I meet. I’m available every day from 10am to 5pm, which allows me to provide consistent and reliable care for your pets. I can easily fit into your pet’s routine for walks, feeding, playtime, and check-ins during the day. I’m dependable, flexible within those hours, and focused on making sure your pet feels safe, comfortable, and well cared for while you’re away. priorities. I make sure to follow your instructions closely and keep your pet in a secure, clean, and calm environment. I pay attention to behavior, routines, and any specific needs to reduce stress and keep them happy. In your home, I respect your space while providing attentive, reliable care. I’m patient, responsible, and focused on building trust with both you and your pet.
“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!!”
“We are so glad that we found Vanessa to be able to watch our dogs while we were out of town. She is so attentive to the needs of our dogs and treats them like her own. She is very knowledgeable about anxious dogs which makes us feel so much better knowing that she is the one taking care of our dogs when we are away.”
About: As a child I've grown up with multiple animals as animals as pets, including a few dogs and a few cats. Professionally, I've had four total years taking care of different animals, which includes supervising dogs as well as helping various animals such as cats, guinea pigs, and other animals get adopted. I have had general experience feeding, walking, bathing, nail trimming, and over all playing with and supervising dogs. I also have had experience taking care of elderly and disabled animals, which includes but is not limited to a 19 year old cat with arthritis and kidney disease. I have experience giving animals oral medications at the correct times and have been consistently. As of right now, I am offering house sitting, drop-ins and dog walking. As of right now, all seven days of the week are generally free for me and I am home most of the time. However, there may be some days where I'm not available, such as certain holidays or family events. If something happens where I can't take care of your animal(s) (such as an emergency), I'll try to let you know ahead of time. I'll always keep your animals supervised regardless of whatever service I'm doing at the time. If your animal takes medications, I'll administer them at the correct times.
About: I currently work at a veterinary hospital, where caring for animals is part of my daily routine. I have hands-on experience with feeding, administering basic care, monitoring behavior, and handling pets of all temperaments. I also have cats of my own, so I understand the importance of patience, comfort, and routine. I’m confident caring for both dogs and cats, including those that may need extra attention, and I always treat every pet like my own. I work Monday through Friday at a veterinary hospital, so I’m already actively caring for animals throughout the day. I’m available for pet care services in the evenings after work and fully available on weekends. My schedule allows me to provide consistent, reliable care while still giving your pet plenty of attention and time. Your pet’s safety and comfort are my top priorities. With my experience in a veterinary setting, I’m trained to recognize signs of stress, illness, or unusual behavior. I take time to learn each pet’s routine and needs to make them feel as comfortable as possible. Whether I’m caring for pets in my home or yours, I provide a calm, clean, and secure environment and follow all instructions closely.
About: I've loved pets for as long as I can remember. I have a true passion for caring for any animal in need and will always treat them with the same love and dedication as my own! Pet care fits seamlessly into my daily routine. I manage my time carefully to ensure pets get consistent attention, dedicated exercise, timely feedings, and structured drop-in visits or walks throughout the week and on weekends I prioritize the safety, health, and well-being of every pet in my care. I provide a calm, comfortable environment where pets can relax freely, alongside wholesome, high-quality, non-GMO organic treats and food tailored to their needs!
“Clarke was great! Took the best care of my Hazel girl. She gets some separation anxiety, but Clarke was so sweet and attentive that I was able to relax knowing my pup was in good hands.”
About: I love Dog and Cat to be honest I really love all animals I really got all my experience from my BestFriend Autumn The Dog Trainer any time my family and friends leave town I’m the 1st person that go to and Autumn The Dog Trainer is mines go to I’m Ben working from home because of the pandemic and I only go in the office if I really need to and only be gone for a hour or 2 and I’m really only 7 mins from my Job I work on Bowling Air Force Base so I’m never to far away from your pets I care for my clients pets like they are my own like family. No pet should feel uncomfortable again this is A Home Away From Home I'm currently work from home so I'll have plenty of time to play and walk with your pups! I'm available for boarding on weekends and weekdays I alway walk with a leash and an open eye for dogs that are not on one and one friendly dog to keep your baby company. I don’t crate dog when I’m home and I’m home 97% of the time unless I’m going to the store and someone is alway if not I can easily crate your dog if needed...
The median cost per night for house sitting in Chesapeake Beach is $50
Pet parents share their Rover experiences - Chesapeake Beach
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 on Rover is $52 per night as of October 2026. Most bookings cost between $34 and $118 per night. 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 October 2026, there are 4,402 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.
<b>Tip:</b> 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 , 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 .
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 .
sitters on Rover set their own , 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
- 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.
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