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.
“Sam did a great job wirh my animals, my house was clean when I came home. She communicated with me during the blizzard and was very confidant in what to do if the house lost power. I received plenty of updates on my fur babies. I highly recommended her for dog and house sitting duties.”
About: I’ve grown up with animals & love being with them. All breeds, no discrimation here! I never get tired of playing with them & treat every pet as if they were my own. I have 10+ years experience in the pet sitting for friends/family & have always had all kinds of animals myself. Experience potty training puppies, helping break bad habits of older dogs, administering medications. Experience with pocket pets as well. I’d love to be your sitter! I am out of town 2 weeks out of the month, but otherwise I can do mostly any day at any time. I would love to check in on your pets! Walking, playing, feeding dogs. Playing, feeding, entertaining cats. I can administer any medications that are needed. I always double check that house doors & kennel doors are secured before leaving. I love them like they’re my own!
“This was our first time using Kyle and we will definitely use him again! He is great with communication and clearly loves dogs. He took care of our home and dogs impeccably.”
About: I've taken care of several dogs and cats for friends and neighbors, whether that's just checking in or staying overnight. I am avaliable to accompany the pets for extended hours or days. Pet sitting is my full time job, so I am usually available whenever! I'm able to either stay with the pets or check on them periodically. I am able to watch pets at a client's house, always keeping an eye on them and making sure they're doing alright. I prefer visiting and/or staying in their environment, making sure the pets more comfortable and less stressed.
“Regina took great care of our fur babies and our house while we were away and we are very happy. She provided regular updates and ensured our dog had plenty of play time and even socialization. We would not hesitate to hire her again”
“Maykayla was a wonderful house sitter. The dogs were well-taken care of & seemed very fond of her. We returned to a clean house — taking care of any pet mess. She communicated often & well with me —sent pictures and videos of the dogs. I would recommend her to any pet owner searching for a kind & trustworthy house sitter.”
About: We love dogs! We are called first when any of our friends go out of town. We have cared for dogs of all sizes and ages from older doxies to young mutts and we love large rotties too. We are also okay with special needs dogs and we make sure your dog gets their medications when scheduled. Our lab loves to make new friends with dogs of all sizes. We have a nice privacy fenced in back yard with a kiddie pool to help the dogs keep cool during the summer even though they will spend most of the time inside. Please know that if your pup stays with us he or she will be treated like a part of the family. We love dogs! I help my Dad on his farm only when I'm not scheduled to care for a pup I'm hosting. I'm free to stay at home all day with your pet. I always keep an eye on what's going on. I'm usually outside if our pups are. If I'm watching a pet at your home, I don't make messes.
“Sammy is the best sitter! My dog is generally anxious and struggles with separation, but he is always content and happy when I return because of the attention and love he receives from Sammy. She’s my go-to and I can’t recommend her enough!”
“We could not be more pleased with Jonna. She kept us informed with just enough texts and pictures that we knew thery were being well cared for. One example included "We all fell asleep on the couch last night." We knew all was well as that is typical of my wife and her "babies". We will would give 10 stars if we could.”
About: I have trained my border collie puppy to do all the basic tricks as well as be calm in public as a hyperactive dog breed. I work full time at a law firm but my free time is ideally spent with pets! My dog and I have a routine for our walks and play time around it so he gets all of his attention. I live on land so my 2 dogs (Border Collie and Golden Retriever) have lots of area to run around and play but it is also fenced in and they never stray. We also have a trail behind the house for walks without disruption. Sometimes we will go to the park for walks or training as well for interaction. We also have kennels in the garage and outside. Caring for pets in a clients home would be completely decided by said client and I would respect their wishes to the best of my ability.
“Aubrianna did a great job caring for our two cats and Home. She sent pictures several times throughout the week giving us additional peace of mind! We would definitely hire her again!”
“Olivia took great care of our three dogs and an axolotl. She stayed at our house and was a very considerate guest leaving the house clean upon her departure. She was very easy to work with. I can’t be more happier with my decision to hire her to watch after our dogs. I highly recommend her.”
“Laura treated our dogs well. She sent us pictures thru ought the weekend which was nice. And they seemed very happy when we got home. Plus she was an excellent house guest by washing the sheets and towels before we got home.”
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.
About: I have grown up with animals of all kinds, plus have years of pet sitting experience for friends & family, even interned at the Dickerson Park Zoo for a summer! Im just new to Rover! I love animals, of all kinds and sizes! I can’t wait to meet you & your pet or pets! I have a pretty flexible schedule, I take care of my own pets daily along with running errands and other daily activities. Pets have always been a big part of my daily life! I unfortunately can’t do boarding but I will gladly stay at your home to make your babies as comfortable as possible! Meeting before you leave allows us to go over their normal routines, feeding, what they love to play. I will gladly dance or sing for your dog to get them to sing, tell me all about your pets silly quirks! Honestly, with my pets weird habits or quirks, nothing phases me anymore! I will not ever judge you for making up a dance just to get your pet to eat.
“Bree went above and beyond for our three animals and our house. Everything felt clean and fresh when we got home, which is an ultimate luxury after being away for several days. Genuinely the best person I've booked on Rover. Bree gave lots of updates and had great questions before and during her stay. Can't wait to book her again!”
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.
Meet local sitters who will treat your pets like family
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 August 2026, there are 238 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 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. On Rover:
- 100% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 100% 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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