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 11% and taxes will apply.
“First time using Jordan and she is an absolute gem!!! Consistently sends updates, makes sure she is on page with all of your doggies requirements, and sends all the pictures. I always feel uncomfortable leaving my babies in someone else’s hands but they took to her so quickly and I can see why! She is a sweetheart. Kind, caring, and full of love. Will a million % be using her in the future”
“Hannah was able to help on short notice when I had to unexpectedly extend a trip due to illness. She asked lots of questions to make sure she was on top of everything, especially since we weren't able to do a usual meet and greet in advance. She kept me informed about the pets during her entire stay. Her willingness to be flexible and communicative made an awful situation less stressful.”
“Felicia was amazing! We came home to happy dogs and a clean home. Thank you for everything. We’ll be in touch for another upcoming trip we’ll need your services for!”
“Jupiter decided to give our sitter Amanda a bit of a scare, but she handled it all right and took good care of our old man. I think Jupiter enjoyed making a new cuddle buddy. 😊”
“Erin is amazing!!! Super sweet, personable and communicative. Our animals love her. We will definitely be seeking her for future sittings & recommending her whenever we can.”
“By far this was the best experience I have ever had with a pet sitter. So trustworthy, reliable, on time. So professional ! We received lots of pics with daily updates. Will definitely use Alyssia again the next time we need a pet sitter.”
“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!”
“Abi and Jordan were great. I came home to a happy and healthy pup. They sent me pictures throughout my trip and made sure she was well cared for. I’ll definitely use them again!”
“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!!”
“Benjamin and Vincent took amazing care of our rescue dog, Romey, while we were out of town for the weekend. This was our first time using Rover and we had complete peace of mind leaving Romey in their care. They provided plenty of updates, were timely, and most importantly we came home to a very calm, content, and happy boy. You can tell they are absolute animal lovers and your pets will love them too!”
“Breezy was awesome! We were out of town for 5 nights and needed someone to take care of our 16 year old, anxious, deaf mini dachshund - Breezy took on the challenge and was great with her! I would definitely recommend Breezy to anyone with an elderly and anxious pup!”
“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.”
“Miranda was such a huge help for staying with my 3 rowdy dogs when I went on a weekend trip. She provided AMPLE photos (which I loved), was so understanding with my anxiety about leaving them, and provided great updates. She was also quick to respond when I texted her to check in & most importantly, made sure my epileptic one got his meds on time. My dogs LOVED her, they looked so happy in the photos & when I would check my yard camera, they loved the playtime, snuggles & all of the attention they received. I will 100% be using Miranda for future bookings, and I would encourage any other pet parent to do the same!”
About: I've been around animals almost my whole life, I use to walk my neighbors dogs all the time and I've trained some puppies before. I'm also have patience for them. I have a lot of free time but I live with my grandmother and my cousin who goes to school so I have to wait for her to get off and on the weekends im free all day. I have a fenced in yard. My dogs are friendly but my bigger dog doesn't do well with other dogs. I also have 3 cats and they get well with my dogs.
“Chelsey is a fantastic dog sitter. This was our first time leaving our dog with a sitter, and Maggie loved Chelsey. She was on time and kept me informed of how Maggie was doing. My home was clean, and everything was great when we returned. I will definitely be using Chelsey again. She is a real dog lover!”
The median cost per night for house sitting in Chesapeake is $45
Pet parents share their Rover experiences - Chesapeake
Ian was fantastic and took excellent care of our dogs while we were away. He kept us updated with regular photos and messages, which gave us peace of mind. Our dogs were happy, well cared for, and clearly enjoyed spending time with him. We would absolutely book with Ian again and highly recommend them to anyone looking for a reliable and caring dog sitter!!
Hannah did a great job looking after both my dog and my home while I was away. She sent frequent updates and photos. She observed and reported that Lexie's allergy symptoms were exacerbated so her medication could be adjusted. Hannah even managed an unexpected home maintenance issue that arose during her stay. I came home to find my home in perfect order and my dog well-cared for. I highly recommend Hannah to anyone who is 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.
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 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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