House Sitting Chesapeake
Find a loving house sitter to watch over your pets and your home.
Over 369 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”
“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!”
“Jazmin stayed the weekend in our home and took care of our two dogs, a Rat Terrier and a Rottweiler. Jazmin sent us pictures and gave us updates on the pups while we were out of town. We came home to two happy dogs and our home in perfect condition. Thank you Jazmin!”
“Peace of mind is priceless! Leaving our dog with Brieana is just that! We can enjoy ourselves while knowing our Zeke is in great hands. We believe he knows that too :)”
“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!”
“Amy was amazing with our fur babies, she cared for them they like they were her own and we felt so safe and comfortable with her in our home. We 100% would recommend to friends or family !!”
“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. 😊”
“Kayla was amazing! She took wonderful care of our fur baby while we were gone and made sure to send multiple updates along with pictures every day. We will be rebooking her whenever we need someone to watch him again. We will also be recommending her to any and all friends looking for a wonderful, reliable sitter. 10/10 recommend!”
“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.”
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.
“Renee is enthusiastic, loving, and caring. She kept us well informed and ensured every animal in our house was well taken care of. She will be our first choice for any future pet sitting needs.”
“I highly recommend her to anyone looking for a trustworthy and caring pet sitter! She took wonderful care of my two dogs during an overnight stay and went above and beyond to make sure they were comfortable and well cared for. She was incredibly attentive, patient, and kept me updated throughout their stay with messages and photos, which gave me so much peace of mind. It was clear that she genuinely cared about my dogs and treated them like her own. I will definitely be booking with her again in the future. Thank you for taking such great care of Bora and Fiji!”
“Christine was so sweet, responsive and reliable! Our dog warmed up to her quickly and we came home from a weekend away to a happy pup! We will definitely book her again and would highly recommend her!”
“Did a great job taking care of Luna (dog) and KB (rabbit) over the thanksgiving holidays. He was able to take Luna on a walk and get her out of the house which was perfect for her. Would re-book again in a heart beat for my next travel needs.”
“Kim has been amazing throughout my time away from my dogs. Kept them on their schedule, made adjustments when my travel plans unfortunately got changed. I will definitely be rebooking with her in the future.”
“Benjamin and Vincent were AWESOME with my absolute weirdo of a fur kid. Phoebe is a rescue with some trauma in her past, so it usually takes her a long time to warm up to new people. The first day she met Benjamin and Vincent, she was a bit standoffish and nervous, but they were SO patient with her and fully understood dog body language and got down on her level and let her approach at her own pace. By the first night, Benjamin had already sent pics of Phoebe snuggling with Vincent, and she was snuggling with BOTH of them and even bringing them her Pig (her most treasured toy that only her besties get to lay a hand on 😂). I would recommend Benjamin and his husband Vincent to anyone, but most especially to anyone with a Nervous Nellie type dog. These guys are SO compassionate and sweet, and my dog picked up on that right away. I had complete peace of mind with her in their care! Thank you both!!”
The median cost per night for house sitting in Chesapeake is $44
Pet parents share their Rover experiences - Chesapeake
I highly recommend her to anyone looking for a trustworthy and caring pet sitter! She took wonderful care of my two dogs during an overnight stay and went above and beyond to make sure they were comfortable and well cared for. She was incredibly attentive, patient, and kept me updated throughout their stay with messages and photos, which gave me so much peace of mind. It was clear that she genuinely cared about my dogs and treated them like her own. I will definitely be booking with her again in the future. Thank you for taking such great care of Bora and Fiji!
Hannah was amazing with our fur babies. She gave them lots of attention, sent regular updates, helped handle a plumbing situation, and even started a treatment for our dog, when she noticed an issue with him. Highly recommend her services. You will be leaving your pets in good hands.
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!!
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.
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 August 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 August 2026, there are 1,325 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:
- 95% 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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