House Sitting Chester

Find a loving house sitter to watch over your pets and your home.

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Over 88
pet parents in Chester have booked house sitting

Chester, 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.

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Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$32
per night
5.0 out of 5 stars
• 219 reviews
62 repeat clients
10 years of experience
Chester, VA, 23831

“We are repeat customers and we just adore Allison! She is so prompt with responses and keeps us up to date with our pets! Our fur babies are always in good hands with her!”

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Victoria A.
Sitter Profile Image: Crystal A.
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Crystal A.
from
$63
per night
5.0 out of 5 stars
• 15 reviews
10 years of experience
Chester, VA, 23831

“Crystal was AWESOME, and I was so appreciative of her taking my very last minute booking. She was so professional and did such a great job with my dog and my home. I came home to an organization house and a very happy dog. I would definitely hire her again!”

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Ada H.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$60
per night
5.0 out of 5 stars
• 41 reviews
21 repeat clients
18 years of experience
Chester, VA, 23831

“Jessica was so kind and flexible with our needs. She loved our girls so well and took amazing care of them. We received so many photos and videos of our two happy pups it made all the difference. Highly recommend and will be using her again!”

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Brielle O.
Sitter Profile Image: Michelle C.
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Michelle C.
from
$60
per night
5.0 out of 5 stars
• 16 reviews
2 repeat clients
10 years of experience
Midlothian, VA, 23832

“This was our first time using Rover, and we couldn't have had a better experience with Michelle. She was responsive, communicated with us, and sent photos to reassure us that our dogs were doing well. She really went above and beyond to care for our dogs and our home while we were out of town for the weekend. We would highly recommend Michelle for any dog sitting service!”

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Elizabeth S.
Sitter Profile Image: Hailey T.
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Hailey T.
from
$50
per night
4.9 out of 5 stars
• 27 reviews
15 repeat clients
15 years of experience
Chester, VA, 23831

“Hailey was wonderful. She was able to watch our dogs last minute.they are big dogs and she handled them well.”

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Grace Jackson J.
Sitter Profile Image: Rebecca B.
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Rebecca B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 48 reviews
20 repeat clients
20 years of experience
Chesterfield, VA, 23234

“Rebecca is a fantastic sitter! She feed and walked Molly early each morning and played with her throughout the day. Molly got so much love and attention while we were away for the holidays and definitely loved Rebecca.”

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Alysha C.
Sitter Profile Image: Tyeir D.
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Tyeir D.
from
$35
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
20 years of experience
Chester, VA, 23836

About: I’ve been around animals my entire life. My oldest fur baby (cat) will be turning 20 this year. I also have two small dogs that are 15 and 11 years old. I love animals. I’m currently a full time student. So I can come and love on your fur babies for you while you are away on a trip or at work. Pets are welcomed in my home and are treated with respect. All animals deserve love and attention. I can love on them for you while you are at work or on a trip.

Sitter Profile Image: Kendall V.
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Kendall V.
from
$45
per night
5.0 out of 5 stars
• 7 reviews
12 years of experience
Shockoe Bottom, Richmond, VA, 23223

“Kendall was beyond friendly and responsible. She was extra caring communicating with us before we booked with her, sending her ETA when she came for a meet and greet when we were looking for a house and dog sitter. Kendall is the perfect house sitter as she is self employed and therefore can do a lot of work from home. She let us know exactly when she had outside commitments such as business meetings so we knew our pup would have plenty of company while we were gone. She also asked many questions to make sure she knew exactly what we were hoping for in terms of care. We received many updates and photos while we were gone and Kendall sounded like she generally enjoyed everything about taking care of our pup. Kendall left our home in spectacular condition. Thank You Kendall!”

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Barbara L.
Sitter Profile Image: Jeanleshea E.
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Jeanleshea E.
from
$55
per night
10 years of experience
Chesterfield, VA, 23832

About: I've owned a dog for some years. I watched other people's dogs from puppies to older dogs. I plan on treating your animals with care. I'm currently working a full-time job. But I most certainly have time in the evening and the weekend to dedicate to the care and well-being of your pet. I'd provide meals, restroom breaks, walks and playtime throwing of the ball, games, play dates or care for pet. Companionship while the owner is away.

Sitter Profile Image: Airlea e.
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Airlea e.
from
$85
per night
5.0 out of 5 stars
• 5 reviews
13 years of experience
Richmond, VA, 23237

About: I have over a decade of professional pet care experience as well as a lifetime of personal pet care experience. I prefer to work with the elderly or medically complex pets as I know they need special attention, adherence to routines, and a calm environment. I focus on providing fun daycare and boarding for pets that don’t do well in regular boarding facilities and require a more home-like experience. Prices are negotiable after a meet and greet. Please fill out your profile in full before meeting! Incomplete/no profile image profiles will not be given my address. I work from home so I spend a majority of my day with my pets and guest pets. Dogs are given mostly free range inside and allowed outside into the huge fenced yard many times a day. They get playtime with other pets and alone time when needed. Our yard is fenced and our house is doggy proofed to avoid trash cans, toilets, and non-chewable items from being accessed. Dogs are crated when they can’t be supervised.

Sitter Profile Image: Janet S.
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Janet S.
Star Sitter
from
$25
per night
5.0 out of 5 stars
• 73 reviews
20 repeat clients
35 years of experience
North Chesterfield, VA, 23234

“I’m so happy I booked with Janet! She is very communicative and kind and my cat quickly took to her. I felt confident leaving my cat and my apartment in Janet’s hands, and I came back home to a happy and cared for kitty.”

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Jessie B.
Sitter Profile Image: Richard L.
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Richard L.
from
$35
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
13 years of experience
Richmond, VA, 23236

“Richard was great and our pups loved him. He gave us updates and pictures and left the place cleaner than he found it! Highly recommend for your pet care.”

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Richelle L.
Sitter Profile Image: Destiny R.
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Destiny R.
Star Sitter
from
$28
per night
5.0 out of 5 stars
• 8 reviews
3 repeat clients
9 years of experience
Richmond, VA, 23234

About: I have two dogs of my own one of which I trained to be my personal service dog. My second dog we originally were fostering and we adopted her because she fit into our family perfectly and became our other pups best friend. I actively foster puppies and kittens. I’ve done crate training and all the potty scaries with puppies. I’m extremely patient with them and try to meet each dog where they are at. I have experience giving medications to pets as one of my cats has to have daily oral medication. I love my pets and would treat yours as if they were my own 🖤 I have a very flexible schedule and I’m on the road and I have free time during the day and evenings where I am able to fit pet care-sitting into my schedule. I’m a very attentive pet parent myself and don’t typically leave my own dog unattended outside in the yard and I try to be very interactive and engage so they can play. I have 3 cats and enjoy playing with them and spending time with them so they feel cared for.

Sitter Profile Image: Allison F.
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Allison F.
from
$35
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
20 years of experience
Northern Barton Heights, Richmond, VA, 23222

“Allison is a terrific person to take care of a house and pets. Good communication, willing to bend as needed. She pet-sat during the single month when my long-haired dog sheds constantly. We have to be vigilant with cleaning the house to keep up with it. She left the house super clean. I felt like a real adult was taking my place. She's not the type who will accept a job, then change her mind and leave you stranded. She's responsible, a person who could manage any situation as well as could be expected, and is up for what comes her way. Allison kept up with our flight arrivals and offered to stay an extra night if we experienced cancelations. She visited first and I showed her the routine which is just so helpful. All good!”

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Beth M.
Sitter Profile Image: Collette J.
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Collette J.
from
$40
per night
4.8 out of 5 stars
• 32 reviews
8 repeat clients
25 years of experience
Richmond, VA, 23228

“Collette was a dream sitter. Stayed full time with my senior pups and my house was exactly as it was when I left. No dishes in the sink, no mess. If anything, they are exhausted from being spoiled to pieces. It’s hard to find a sitter who won’t leave the pups alone for hours on end…if you’re looking for someone who truly cares, book Collette!”

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Ashley D.
Sitter Profile Image: Nicholas C.
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Nicholas C.
from
$38
per night
5.0 out of 5 stars
• 12 reviews
1 repeat client
10 years of experience
Richmond, VA, 23220

“He did a great job with our pets while staying with them! It was nice to know that the animals had someone reliable and attentive looking after them while we were away, and that they could stay where they were comfiest, at home! He handled all of our (and our pets) needs wonderfully and we would gladly have him sit for us again.”

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Astrid O.
Sitter Profile Image: Shanna K.
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Shanna K.
from
$60
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
10 years of experience
Richmond, VA, 23236

“Shanna was an excellent caregiver for dog, Tessa, while we were out of town. She was attentive to our girl’s additional needs, administering medications and care for Tessa’s health issues. Shanna kept us updated throughout the week and was responsive to any questions we had. We highly recommend her!”

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Sarah M.
Sitter Profile Image: Madelaine E.
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Madelaine E.
from
$65
per night
5.0 out of 5 stars
• 89 reviews
45 repeat clients
50 years of experience
Eastland Park-Dixie Plantation, Richmond, VA, 23230

“Madelaine did an amazing job house sitting and taking care of our dog, LuLu. She was responsive, attentive, and kept us up to date with LuLu by providing photos. We will definitely hire her again!”

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Patrick A.
Sitter Profile Image: Kimberly S.
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Kimberly S.
from
$45
per night
35 years of experience
Richmond, VA, 23235

About: I’ve taken care of pets for 35 years. I am able to administer medications including injectable’s if needed. I work with all breeds and temperaments, and do not shy away from pets that have behavioral issues. I’ve worked extensively with large farm animals to include horses, goats, donkeys, and cattle and have cared for the occasional parrot, chinchilla, and snake. Since pet sitting is my only employment, I am able to provide companionship to your fur family 14-18 hours daily including overnight care. I also am able to check mail, grab packages, and water plants at no additional charge. I keep to your pets normal daily routine, to include walks, potty breaks, feeding schedule, and of course nap times. Let’s set up a meet and greet to see if I’m a good fit. Currently I am only doing pet sitting and it’s my primary and only employment. This enables me to spend more time with your fur babies. I care for pets in your home as requested. I stick to their normal daily schedule. I also water plants and grab mail as needed.

Sitter Profile Image: Annelise W.
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Annelise W.
from
$27
per night
12 years of experience
The Fan, Richmond, VA, 23220

About: I've been pet sitting since I was a little kid and grew up with dogs and cats, and since I work from home full-time, I have a flexible schedule. I love getting outside for walks and tend to walk 10k steps daily, so if you have an active dog, I’m your girl! I don’t currently have pets of my own, so I love getting to spend quality time with yours! My ultimate goal is for you to feel confident that your pet is safe, happy, and well cared for while you’re away. I work from home from 9am - 5pm, so I’ll be very available during the week. I have set evening plans on Wednesdays and Thursdays, but I have no standing commitments all other days of the week. I will follow whatever protocol you have for your pets. Whether that’s a specific routine, individual needs, and/or keeping you up to date with pics / messages. I want you to feel like your furry friends are in good hands!

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The median cost per night for house sitting in Chester is $50

Pet parents share their Rover experiences - Chester

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5.0 out of 5 stars

We had such a great experience with Rangeen! She was wonderful with Oliver and Lola and sent us frequent updates and pictures, which we really appreciated. She was incredibly attentive, patient, and thoughtful with both of them and handled everything that came up during her stay so well. It was such a relief knowing they were being genuinely cared for while we were away. We came home to two happy pups and would absolutely trust Rangeen with them again!

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Brittany R.
House Sitting
5.0 out of 5 stars

Meghan was great once again. She took care of both of our puppy dogs and kitties. Our shy kitty even came out multiple times to say hello (which he does not do for most people). Everyone was well taken care of and we came home to happy animals and a clean home. We would recommend Meghan to anyone for animal and home sitting!

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Danielle S.
House Sitting
5.0 out of 5 stars

Sabrina took care of my dog diesel and sent pictures daily. He was very happy and enjoyed his time with her

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Jason C.
House Sitting
5.0 out of 5 stars

This is our first time with Maddie and we couldn’t have been happier! She stayed at our house; one of our dogs had never been with a sitter or boarded and Maddie was gentle and caring with him. Thanks, Maddie Kevin, Carlos, Kathy and Mark ❤️❤️❤️

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Kathy T.
House Sitting
5.0 out of 5 stars

Jessica is great and Grey enjoyed her company. She also went the extra mile for my last minute planning and watered my garden. We will use her services again!

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amy a.
House Sitting
5.0 out of 5 stars

Cassidy is the best! She took care of our girls like her own, and was more than willing to help with an impromptu vet visit when it looked like one of our dogs had a UTI (she didn’t she was just being a weirdo). We will definitely be reaching out to her again. The communication and picture taking are a 12/10. :)

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Alyssa J.
House Sitting
5.0 out of 5 stars

Mia was absolutely INCREDIBLE!!!!! She would constantly send picture updates and made me feel secure as a nervous dog mommy. I will definitely hire her again and will recommend her to anyone needing a petsitter.

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Abigail P.
House Sitting
5.0 out of 5 stars

Phyllis did a fabulous job with our two dogs while we were away this past weekend. Callie & Howie can be wary of strangers, but they very quickly trusted Phyllis. We look forward to other trips knowing our fur babies will be in good hands.

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Michele P.
House Sitting
5.0 out of 5 stars

Melanie took great care of our pup and home as always. She sent a lot of pictures and updates. Will definitely use her services again.

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Rochelle D.
House Sitting
5.0 out of 5 stars

Linda did a fabulous job taking care of my two dogs, one of whom can be a bit tricky with people he doesn't know. From the start, I appreciated Linda's professional yet laid-back manner. Communication remained top-notch before and during our trip. It was so nice being able to relax knowing our dogs were in great hands. We absolutely hope to use Linda again!

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Jenna D.
House Sitting
5.0 out of 5 stars

Anabella was respectful of our house and provided photos and updates on our pups. We would be thrilled to have her in our home again.

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Kerry-Ann P.
House Sitting
5.0 out of 5 stars

Brandie was amazing and kept us informed the entire week we were away. Jack, our dog was relaxed and well exercised when we came home. The house was neat and as we left it. Looking forward to hiring Brandie again for the next time we leave town.

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Tamar B.
House Sitting
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  • 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?

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

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Popular requests for house sitting - Chester

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Sitters in Chester average 4
repeat house sitting clients

FAQs for House Sitting - Chester

Frequently asked questions about Rover

The average cost of House Sitting in Chester is $50 per night as of October 2026. Most bookings cost between $38 and $80 per night. On Rover, 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 1,458 sitters on Rover offering House Sitting across Chester. 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 Chester 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 Chester 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 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!

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 , 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 .

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 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 .

sitters on Rover set their own , 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.

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

  • 91% of sitters can help with special care needs
  • 95% 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.

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