House Sitting Chesapeake
Find a loving house sitter to watch over your pets and your home.
Over 348 pet parents in Chesapeake have booked house sitting
Chesapeake, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 15% and taxes will apply.
“I have booked with Felicia three times now, and she has consistently provided a great experience. What stands out most is her attention to detail; she asks a lot of questions upfront to make sure she fully understands my dog's routine and comfort levels. It’s clear she wants to get everything exactly right, which gives me a lot of peace of mind while I'm away. She is reliable, communicative, and truly cares about the well being of the animals in her care. I highly recommend her if you’re looking for someone thorough and attentive!”
“Hannah was a great choice to watch our two dogs and cat while we were away for the week! She sent daily updates and picture the whole time. We would recommend Hannah as a sitter for sure.”
“This is the third time Jordan has worked with us. She is just as amazing every time. Martin is always given so much love and taken care of so well. We really appreciate having someone to watch him that we know he is completely safe and happy with! We will continue to work with her in the future.”
“Erin was amazing! She was very easy to communicate with to set up the booking, asked plenty of questions to make sure Diablo and I were taken care of, and sent me picture and video updates of them enjoying each other's company. If possible, I will book her again in the future!”
“Amy was so great with our dogs!! She walked them, hung out with them, and kept us updated with photos. She was always quick to respond and made us feel totally at ease while we were away. We came home to happy pups and a spotless house - such a great feeling. Highly recommend and would 100% book with her again!!”
About: I’ve been taking care of dogs since I was 11. I recently had to let my two girls go, so I’m looking forward to loving on your babies. I have experience with puppies all the way to senior dogs. Both of my girls needed medication towards the end, so I’m familiar with administering pills on a schedule and anything else that goes with owning a senior dog. My oldest had dementia, so if your pup has that, I can handle the quirks that come with that. I’ve also watched my friends bigger dogs, and they love just as much cuddles as the little ones do. Taking your fur baby out for walks, cuddling with them, and playing with their favorite toys would bring so much joy. You’ll have peace of mind (and updates) if you let me take care of them like you would. I am a teacher, so during the weekends and summer I have all the time to spoil your precious baby. Being a teacher also means I can spend extended time with your pet during the summer. I’m very good at following schedules and routines to help make your pet feel as comfortable as possible while you’re away. I will love on them, play with them, and do anything else you need so both of you feel relaxed while you’re at work or on a trip.
“Tracie is great with my 3 babies! She always shows up on time I always feel safe knowing she is watching over my babies. I would definitely recommend her for any pet sitting needs!”
“Damian took good care of my pups and home while I was away for nearly a week. I appreciated his reliability and communication. He followed the pet care instructions left for him, and I returned to my house in the same condition as when I left. We look forward to hiring him again!”
“Jazmin was communicative, kind and professional. She took wonderful care of our dog and was a great guest at the house. We will be booking again with Jazmin!”
“Adriana was an absolute gem! She took amazing care of my boy Riley!! She sent so many pictures and videos! I think my pup may love her more than he loves us now haha cannot wait to use her again! Has my highest recommendation!”
About: I have had a dog all my life both big and small. I also cat sit and I’m willing to take care of all animals. Helping with your pets helps me be happy:) I am a PA student and I have classes from 10-3 most days. I am available to check in before or after class at anytime. I also am available weekends as well. I currently don’t have any pets in my home. I live in an apartment and I’m willing to go sit at your place or check in on the animals when needed.
“We had such a wonderful experience with Abi while we were away! She took amazing care of Loki and Hazel, and I truly felt completely at ease knowing they were in her hands. Hazel is a very anxious dog and rarely warms up to new people — she never goes on walks with anyone but us — and she actually went out on a walk with her! That alone speaks volumes about the patience, kindness, and calm energy she brings. Both dogs were happy, well cared for, and clearly loved while we were gone. I’m so grateful to have found someone we trust so fully. We will absolutely be hiring her again and again!”
“My dogs had an absolute great time with Renee. She followed all of my dogs special needs instructions medication yard time ect and sent lots of pictures my boy is very picky about his comfort with people but he was sure to sleep belly up even got a picture of it. My girl is pretty easy going too but she also clearly had fun making a mess with her toys. Renee even took the trash out and cleaned up after the dogs which was not expected. Over all very pleasant great communication lots of silly dog pics and a house cleaner returned cleaner than expected we will be using her in the future.”
“Emmanuel was an amazing pet sitter! He watched my 5 fur babies while I was gone for a week and they got along with him so well! He was very attentive to my fur babies and he enjoyed time spent with them! He treated them like they were his own. He was very communicative, providing me daily updates with adorable pictures and videos! He even got my antisocial cat to warm up to him and interact with him, which was a 1st! He also did a great job keeping the place clean while caring for the fur babies. I feel like my pets definitely lucked out with having an amazing sitter and new friend! I would highly recommend booking Emmanuel as your next pet sitter!”
“Morgan was awesome with Ginger and the house. She was engaged with her and made sure she had lots of playtime. She was reliable, prompt, good communicator. and a great listener. She did everything I had asked for. Ginger enjoyed her company :)”
The median cost per night for house sitting in Chesapeake is €45
Pet parents share their Rover experiences - Chesapeake
We could not recommend Sara enough! She has an obvious love for all animals, that translates very naturally into her care for them. She offered a meet and greet before her stay and provided updates throughout the weekend. We absolutely will trust her again with our home and animals, and recommend her to other friends and family in need of a sitter.
Cameron was phenomenal with our Bootsy boy! He was really patient during the initial meet up as Boots took a few minutes to warm up and they were besties by the end of it. Cameron asked great questions to make sure he was fully informed on Boots' routine prior to us leaving. He sent pics and videos throughout and even taught Boots a new spin trick! Our house was left very clean and he stripped the bed for us before we got home to wash things. My husband and I would highly recommend using Cameron to anyone in the area!
London did a fantastic job caring for Millie while we were out of town. She is very communicative and timely in her responses. London’s flexibility to stay an additional day due to a canceled flight made the change of plans way less stressful. We knew Millie was in good hands with her, and would absolutely rebook in the future.
Naja took great care of our 2 dogs and our home while we were on vacation. She sent frequent updates and was comfortable asking questions and informing us of the dogs' behaviour in aour absence. The biggest comment my wife and I have upon our return is that the house was clean and tidy, and the dogs were calm and happy. They had a bond with Naja that was clearly evident even in our presence upon our return. I think that is the true sign of the caring petsitter that Naja is. We would absolutely recommend her and will hope to use her services again.
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 Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Chesapeake sitters!Sitters in Chesapeake average 4 repeat house sitting clients
FAQs for House Sitting - Chesapeake
Frequently asked questions about Rover
The average cost for House Sitting in Chesapeake on Rover is $33.3 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of July 2026, there are 1,321 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:
- 94% of sitters can help with special care needs
- 99% can help with giving oral medications or injections
- 98% 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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