Dog Sitting Chester

Book a Chester dog sitter to watch your dog in your sitter’s home or yours.

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Over 188
pet parents in Chester have booked dog sitting

Chester, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Jamie R.
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Jamie R.
from
$15
per visit
5.0 out of 5 stars
• 2 reviews
20 years of experience
Chester, VA, 23831

“Above and beyond. The experience was better than perfect. She went way above what was asked . We ran out of food for a pet and she went ahead and bought some . I did reimburse her but she still took time out to handle the issue. It’s so wonderful to know that someone would go above what was required and care for our pets as their own . I will request Jamie again and knowing how well she did and how she cares , makes it easier to go on vacation more frequently. Amazing job Jamie . Thank you again”

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Jami F.
Sitter Profile Image: Darnell M.
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Darnell M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 102 reviews
39 repeat clients
14 years of experience
Colonial Heights, VA, 23834

“darnell was amazing! he watched after my 6 month old kitten, 2 month old kitten, bearded dragon and leopard gecko. he was able to feed the kittens their supplements along with my reptiles on their scheduled feeds. he had communicated great and when there were delays on arrival he had updated me promptly. he truly went above and beyond for my little zoo and was great! i will be using darnell again in the future!”

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Ariana R.
Sitter Profile Image: Hana J.
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Hana J.
from
$25
per visit
5.0 out of 5 stars
• 16 reviews
5 repeat clients
17 years of experience
Colonial Heights, VA, 23834

“Hana is amazing! She’s so flexible and understanding when it comes to schedules and demands of each animal in the home. She truly cares about our animals (she will leave our tv on for our dog so she isn’t lonely) and does enrichment treats without us even asking her to. I trust her with our babies 100%”

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Ashley D.
Sitter Profile Image: Journei F.
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Journei F.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
• 9 reviews
5 repeat clients
7 years of experience
Richmond, VA, 23234

About: I’ve been taking care of pets for most of my life. My family and friends have always counted on me to care for our/their pets when needed. I have walked, bathed, fed, snuggled and played with them! I am a full time worker, five days a week, nine hours a day from 9AM to 6PM. And I also have a part-time job that I do on the weekends, but I am still open to any service I could possibly provide for you and your pet! I receive my part-time job schedule weekly schedule every Saturday, so communication is key. I will care for your pets in your home by providing them the care that they need, walks, runs, snuggles, playtime, you name it! If there is anything specific you want me to know or abide by please let me know and I will make sure you and your pet are left satisfied :)

Sitter Profile Image: Grace L.
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Grace L.
from
$20
per visit
5.0 out of 5 stars
• 41 reviews
14 repeat clients
17 years of experience
South Chesterfield, VA, 23834

“We had peace of mind knowing Grace was taking care of our cats. This was a long trip so the photos and reports we received connected us to our cats and made us smile. Thanks for doing such a great job Grace.!!”

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Diana W.
Sitter Profile Image: Tyeir D.
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Tyeir D.
from
$13
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
20 years of experience
Chester, VA, 23836

“Tyeir took great care of my dog, she even remembered something I'd forgotten in my instructions. Very communicative and attentive to my dog's needs, highly recommend.”

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Bridgette T.
Sitter Profile Image: Melanie K.
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Melanie K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 47 reviews
6 repeat clients
10 years of experience
Chester, VA, 23831

“Melanie was absolutely awesome. She was so helpful with all of my needs, and she had no problem at all helping me out with extra issues that came up! She was very responsive and asked great questions, and she did an amazing job engaging with my cats and playing with / taking care of them. I felt at ease knowing she was there to take care of them, and I can’t recommend her enough!”

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Andrew K.
Sitter Profile Image: Hailey T.
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Hailey T.
from
$30
per visit
4.9 out of 5 stars
• 27 reviews
15 repeat clients
15 years of experience
Chester, VA, 23831

“Hailey was wonderful! After another sitter fell through last minute, she was able to help us with only a couple hours notice. She gave us updates and pictures every visit and even gave our Kona a bath. She was also able to get Kya to go outside without a leash. I’m so glad we found her!”

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Brooke L.
Sitter Profile Image: Amanda W.
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Amanda W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 61 reviews
17 repeat clients
15 years of experience
Chesterfield, VA, 23832

“Amanda is pleasant and is very conscientious. She takes time for pets and purrs with our cat. Kallie is shy but loves her. When we come back from our trips, the house is always in good order. We definitely recommend Amanda. She is amazing!”

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Jackie N.
Sitter Profile Image: Sarah I.
Verified Background Check
Sarah I.
Star Sitter
from
$45
per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
7 years of experience
Chesterfield, VA, 23832

About: I've been dog sitting since covid; things have changed but not the love for animals. Since my start I've dog sat for a wide varity of dogs. Puppies, oldies, big, small. Some requiring a lot of attention to help distract them, some that just sit by the door waiting for their pawrents to come home. From medications to special diets, specific schedules and give attention if you have the extra time. I will treat your dog as my own! Something you can count on is they will be loved and well taken care of. Pet care is my top priority. Making sure they are fed on time and they get plenty of play time and walks while you are gone. I unfortunately can't accept pets into my home as I don't currently live alone. But I'm more than willing to stay over whenever you need me to.

Sitter Profile Image: Morgan W.
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Morgan W.
from
$25
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
9 years of experience
Chester, VA, 23831

About: I have previously worked in a kennel at an animal hospital for 3 years, years of house sitting services along with pet care provided on Rover. I have had cats and dogs of my own (pitbull mix and beagle mix). My schedule is flexible to be able to provide pet care services. I'm available for mid-day walks or drop-in visits during 11-2 Monday through Friday. I do not offer pet care services in my home but can ensure to cultivate safety, trust, and respect while offering services in your home.

Sitter Profile Image: Karen T.
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Karen T.
from
$19
per visit
5.0 out of 5 stars
• 5 reviews
2 repeat clients
16 years of experience
North Chesterfield, VA, 23234

“Karen was prompt with her visits while watching our dog over the weekend! She is very professional with communication and very reliable when caring for our dog. We are excited to use Karen again in the future!!”

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Anne A.
Sitter Profile Image: Taylor B.
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Taylor B.
from
$18
per visit
5.0 out of 5 stars
• 9 reviews
1 repeat client
5 years of experience
Henrico, VA, 23231

“Taylor is such an amazing pet sitter! She gives such great updates and takes so many pictures that I basically feel like I'm still home lol. I'd highly recommend Taylor and will be reaching out to her again for future needs.”

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Michelle W.
Sitter Profile Image: Kelsey M.
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Kelsey M.
from
$15
per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
6 years of experience
Chester, VA, 23836

“Kelsey was a friendly companion visit for my mature feline who loves human interaction. Could finally make a needed week long trip feeling good that my pet would be taken care of with fresh food, water, and a regular dependable affectionate visit. Very highly recommended if you want to be able to leave your home and pet family and feel confident they will be taken care of.”

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Bill B.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
5 years of experience
Richmond, VA, 23234

About: Animals have always been a big part of my life. I have over 5 years of experience caring for dogs of all breeds, sizes, and personalities, including my own pets and my professional experience as a kennel attendant at a pet daycare. I’m experienced with walks, feeding routines, baths, medication, and providing care for pets with different needs and temperaments. I understand that every pet has their own personality and routine, so I take the time to make sure they feel safe, comfortable, and cared for. My goal is to give your pet the same attention, patience, and love I would give my own. I have a flexible schedule that allows me to give pets the time and attention they deserve. I plan my days around making sure each pet gets proper care, playtime, walks, and check-ins without feeling rushed. I treat every pet like they’re my own. I focus on keeping them safe, comfortable, and following their normal routine so they feel relaxed while their owner is away. I pay attention to their behavior, needs, and any instructions provided to make sure they receive the best care possible.

Sitter Profile Image: Allejah K.
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Allejah K.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
• 7 reviews
7 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

About: What sets me apart is my calm, low-stress home where I host max 2 compatible dogs at once. Perfect for anxious, selective, or reactive pups who need peace over chaos. I also offer solo-stay pricing for dogs who need to block my second spot. My experience shines with senior dogs (gentle mobility support, meds) and high-energy mediums (structured play without overwhelming them). I work less than 10 minutes from home and have a flexible schedule that allows me to check in during my breaks for walks, playtime, and potty breaks. While I’m away, I use indoor cameras to monitor pets and ensure their safety and comfort. I’m fully available and home on weekends, so your pup will get plenty of attention, care, and activity throughout their stay. I don’t have any pets of my own currently. I have a nice size fenced yard and I love taking pups on long walks in my neighborhood or at the local dog park if possible. You can also book my backyard on Sniffspot!

Sitter Profile Image: Tianna L.
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Tianna L.
from
$28
per visit
4.5 out of 5 stars
• 8 reviews
2 repeat clients
5 years of experience
Courthouse, VA, 23832

About: I’ve taken care of my sisters dogs in the past, also owned many dogs growing up. My daughter LOVES them. My availability is pretty open! We would love to meet your furry friends. I’m in college and and i’m not currently working. My availability is open so that I will have plenty of time to care for your furry friend. We love animal's in my home we will treat them as our own of course. My place is clean and taken care of perfect setting.

Sitter Profile Image: Melissa M.
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Melissa M.
from
$38
per visit
5.0 out of 5 stars
• 5 reviews
2 repeat clients
30 years of experience
Chester, VA, 23831

About: I've cared and been around pets and dogs of all breeds all my life. My family has always had dogs so I have experience feeding, grooming, playing, walking, administering simple medication, and basic training. I'm a mom of 7 that works part-time, with little ones in school, so I have the means, time, professionalism, and drive to play and care for your four legged family member, when your unavailable to.... And your able to rest assure that they are well taken care of :) When caring for pets I am able to visit and care for them in their natural setting.... Of their home, so they more natural and relaxed. Please reach out if your interested in weekend boarding at my home.

Sitter Profile Image: Layla H.
Verified Enhanced Background Check
Layla H.
from
$18
per visit
7 years of experience
Chester, VA, 23831

About: I’ve been taking care of animals since I was 11 and I have taken care of a bunch of different animals in that time. I’m currently unemployed looking for jobs so I’m all free! I will be available pretty often. I will be doing online school around October and will be asynchronous and online. I am available very often. I can stick to pet routines and any medication and dietary needs. I would sometimes be accompanied by my boyfriend who can be an extra eye.

Sitter Profile Image: Nadra W.
Verified Enhanced Background Check
Nadra W.
from
$25
per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
12 years of experience
Chester, VA, 23836

About: I have been taking care of dogs since I was 10 years old and I am 22 now. I consider dogs to be one of the many keys to happiness so I treat them as such. Whether that be long walks in the neighborhood, endless cuddles, or a friend to play with, they get what they need. I have never discriminated against a dog based on size or breed because all dogs deserve love and care no matter what. I take care of my dogs to the best of my ability so I will always do the same for others. You can be assured that they are in good hands. So if you need someone to love and care for your dog when you're not there I'm your girl! I am currently the primary care taker for my family dog, Raine. This includes walks 2x day, feedings, bath, etc. I ensure he takes his medicine, has lots of play time and clean bedding. I do not currently care for other dogs in my home. However, in my client’s home I ensure that the space is clear and void of anything that could bring harm to their pets. I make sure to regularly check up on them and listen to their needs.

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The median cost per visit for dog sitting in Chester is $20

Dog parents share their Rover experiences - Chester

1 / 1
5.0 out of 5 stars

Abby was awesome, and my fur babies loved her. I will definitely be using her as a pet sitter again!

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Katelyn C.
Drop-In Visits
5.0 out of 5 stars

We had such a great experience! She came over ahead of time to meet Duke, Winnie, and Green Bean, and immediately made us feel comfortable leaving them in her care. She was so kind, patient, and attentive with all three of our dogs and treated them like they were her own. You can tell she genuinely loves animals and takes the responsibility seriously. We felt completely at ease knowing our pups were being well cared for. We would absolutely recommend her and will definitely use her again!

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Lindsay Y.
Drop-In Visits
5.0 out of 5 stars

we loved having indiana watch over our pups while we were away! we got lots of pictures and didn’t have to worry about missing them too much :)

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Cassidy R.
Drop-In Visits
5.0 out of 5 stars

Sam is AMAZING!!!!!! I cannot say enough about how lucky we were to find Sam. Unexpectedly, just a few days before a lengthy trip, one of our senior pups suffered a seizure in the middle of the night. We couldn't cancel our trip, but we found ourselves with increased anxiety about leaving the dogs and unable to ask our usual housesitter to potentially administer his new emergency medications. We were immediately drawn to Sam's experience as an ER vet tech, but meeting her surpassed even our wildest hopes: she has such a deep wealth of experience in caring for animals and a real passion for ensuring animals live their best, most comfortable lives. As part of her daily visits, Sam did wellness checks on the dogs and sent us detailed, reassuring updates about how well our dog was adjusting to his new medication. Recognizing their limited mobility, she spent her visits loving on them and doing gentle stretches to help with their joints. We returned to healthy, happy pups, and the peace of mind we were able to find on the trip, especially knowing our medically complex dog was in such great hands, was invaluable. We will happily work with Sam again and cannot recommend her to others more highly!

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Jenna G.
Drop-In Visits
5.0 out of 5 stars

Phyllis did an amazing job with our drop-in visits! She watched our 3 cats and dog, making sure everyone was fed, loved, and well taken care of, which included administering medication. The photo updates after every visit brought us so much peace of mind. We will definitely use Phyllis again!

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Janice L.
Drop-In Visits
5.0 out of 5 stars

Sabrina took great care of our 3 boys. I'm glad my boys got to stay cozy in our home while we were on vacation. Sabrina sent us pictures of each and they warmed up and were playful even excited Sabrina was there. I highly recommend Sabrina she took great care of our fur babies and will book in the future!

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Judith E.
Drop-In Visits
5.0 out of 5 stars

Annabella was an amazing sitter for our dog, Ash! She communicated about each visit and sent us some pics of our sweet boy. She was on time each day and even cleaned his bowls and lick mats for us so we came back home and could get back into our routine easily.

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Katie W.
Drop-In Visits
5.0 out of 5 stars

Tiffany was a joy to work with. Great response time and punctual. She dealt well with our dog’s feeding requirements. Took very good care of our dog, and we really appreciated it.

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Renee P.
Drop-In Visits
5.0 out of 5 stars

Cassidy was very professional and trustworthy! She did 2 drop ins and I was nervous but she made me feel comfortable!

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Liz G.
Drop-In Visits
5.0 out of 5 stars

Charlotte responded promptly with the shortest time possible and gave me some peace while I was away for an emergency. Tech was well well taken care off. Definitely recommend her for your pur

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Anita A.
Drop-In Visits
5.0 out of 5 stars

Brandie always does an amazing job with our pets. We know they’re in good hands when Brandie is taking care of them.

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Kelsey G.
Drop-In Visits
5.0 out of 5 stars

Lisa walked into a mess. It's my father's house who had lived in filth unbeknownst to me, as I live out of state. Despite this, she was kind and understanding. Would recommend to anyone!!!

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Jennifer H.
Drop-In Visits
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Popular requests for dog sitting - Chester

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Sitters in Chester average 7
repeat dog sitting clients

FAQs for Dog Sitting - Chester

Frequently asked questions about Rover

The average cost of Dog Sitting in Chester on Rover is $20 per visit as of October 2026. Most bookings cost between $14 and $34 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 2,400 sitters on Rover offering Dog Sitting across Chester. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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 Chester 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!

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 .

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.

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 .

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Chester with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Chester. On Rover:

  • 93% of sitters can help with special care needs
  • 97% 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.

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.

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