House Sitting Chesapeake
Find a loving dog sitter to watch your dog overnight in your home.
Chesapeake, 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.
“A.J. took amazing care of our little guy! And he has separation anxiety, so he is not always the easiest to take care of! Would definitely highly recommend her and hire her again! She was fantastic!!”
“We had an amazing experience with Rachael! She watched our Rottweiler, Maggie, for an extended period of time and took such great care of her. Rachael was incredibly friendly, kept us updated with pictures, and gave Maggie plenty of love and attention while we were away. It gave us so much peace of mind knowing our fur baby was in great hands. We would absolutely recommend Rachael and will definitely use her again!”
About: I’m an animal science major with lots of different animal experience! I foster with local shelters, extern at a local veterinary office, and pride myself in research/care I’ve taken with my own animals and others. I’m currently a full time student MSU. Most of my classes are first thing in the morning, then I’m available for the rest of the day. I have a completely fenced 1 acre yard with 3 personal dogs who are completely used to new interesting dogs from previous fosters. I kennel all of my dogs and all meals are given separated. No animal in my house is left alone together unsupervised.
“We have used Dakota multiple times in the past couple years and she is amazing. Responsive, able to stay at our home, and doesn't mind our cranky 11 yr old chihuahua lol! Highly recommend her!”
About: I’ve taken care of pets ever since I was a kid, im really considerate of everyone’s time and need of there own time I can help and do anything you may ask even give the pet medicine if that is what is needed I have 4 cats and they are very well trained and loveable. I also help out around the neighborhood in pet sitting so I pretty much know what you will expect of me and I’ll make sure it happens. I give them baths, brush them, feed them, walk them, I’m very calm and time proficient and know what to do in case of emergency
“Brinkley was amazing she took fantastic care of our animals, was very good with communicating with us, and left the house in better condition then when she arrived. Thank you so much for everything and we highly recommend her.”
About: Hi! I’m Alex. I used to work as a vet tech in California, so I’m very comfortable caring for pets with all kinds of needs. I’m especially patient with puppies who are still learning the routine and with senior pets who need a little extra love and support. I can help with things like giving meds, watching for health changes, and adjusting to whatever makes them most comfortable. I genuinely love getting to know each pet’s personality and making them feel safe, relaxed, and happy. Whether that’s playing, doing a little training, or just snuggling on the couch, I’m here for it. Your fur baby will always be treated like family with me. 🐾💛 As a college student, I plan pet care around my schedule feeding before/after classes, playtime between study sessions, and cleaning and errands on weekends or free days. Whether I’m in my home or yours, I do my best to help pets feel safe and relaxed. I take things slow so they can warm up and get comfortable. I keep their space clean, make sure water and food are always fresh, and stick to their normal routine as much as possible. Since I used to be a vet tech, I’m confident giving meds and keeping an eye out for anything unusual. I’ll always keep you updated so you know how they’re doing!
“Tori did an absolutely amazing job taking care of our dogs, Maggie and Louie! She was incredibly detailed, kept us updated regularly, and sent so many great pictures that truly put us at ease while we were away. You could clearly see how happy and comfortable the dogs were in her care, which meant everything to us. Tori is so sweet, kind, and thoughtful. It gave me such peace of mind knowing she was there loving on our pups like they were her own. We will absolutely be using her again and highly recommend her to anyone looking for someone trustworthy and caring! 🐾”
About: What sets me apart is a lifetime of hands-on experience and genuine love for animals. I am a retired Quarter Horse and dog rancher with over 54 years of experience caring for animals of all kinds. Throughout my life, animals have never just been a job—they’ve been my passion, my pride, and my joy. I service BRANSON MO, TABLE ROCK AREA, I am Close to INDIAN POINT, SILVER DOLLAR CITY, AND THE CHATEAU OF THE LAKES HOTEL & RESORTS, 15 MINUTES TO THE ENTERTAINMENT. I live in a private gated and safe community. In addition to running a ranch, I’ve worked as a veterinary assistant, which gives me a deeper understanding of animal health, behavior, and safety. I’m comfortable recognizing signs of stress or illness and responding appropriately. I treat every animal in my care like family. Whether it’s a quick visit or an extended stay, your pets will be cared for with the same attention, patience, and love I’ve given my own animals for decades. Their comfort, safety, and happiness always come first. With my background, you can have peace of mind knowing your pets are in experienced, capable, and truly caring hands. Pet care fits naturally into my daily routine. I work during the day, but I dedicate my evenings and weekends to pet sitting, which allows me to give pets plenty of attention, consistency, and care during those times. My schedule works especially well for pet owners who need reliable evening check-ins, overnight care, or weekend coverage. I make sure each visit is unhurried so your pets receive the attention, exercise, and affection they deserve. Caring for animals has always been a big part of my life, so even with my daytime responsibilities, I prioritize making time to ensure every pet feels safe, comfortable, and well cared for. I care for pets in their home by keeping their routine consistent and their environment calm and safe. I follow all instructions closely, including feeding, medications, and daily habits. With my background as a rancher and former veterinary assistant, I pay close attention to behavior and safety. I also treat every home with respect—keeping it clean, secure, and just as I found it. I provide updates so owners feel at ease, and I treat every pet like my own—with patience, care, and love.
About: Skills Included: -large and small dog experience -puppy training -potty training -1 dog of my own(Australian shepherd) -alpaca barn care -grew up on a farm! Monday through Friday 9:30am-10:00pm for 4 of those days. One day in the week could be earlier if needed. Weekends can be worked out if needed as well. I have a privacy fenced in backyard. I have 2 dogs of my own. They are both extremely friendly with other people and dogs. I have a male german shepherd puppy and a one tear old female australian shepherd. They are up to date on vaccines/flea/tick medicine. They are inside/outside dogs. They get walked daily sometimes twice a day!
The median cost per night for house sitting in Chesapeake is $40
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
Select a filter and find qualifying sitters offering house sitting.Sitters in Chesapeake average 3 repeat house sitting clients
FAQs for House Sitting - Chesapeake
Frequently asked questions about Rover
As of November 2026, there are 250 sitters on Rover offering House Sitting across Chesapeake. 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 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 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 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. On Rover:
- 94% of sitters can help with special care needs
- 96% 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.
Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Chesapeake house sitting needs. On Rover, it's easy to find a loving dog sitter in Chesapeake who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Chesapeake house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Chesapeake for your dog — people who'll treat him like family.
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