House Sitting Chester

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Over 68
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.

1 / 1
Sitter Profile Image: Allison B.
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Allison B.
Star Sitter
from
$32
per night
5.0 out of 5 stars
216 reviews
60 repeat clients
10 years of experience
Chester, VA, 23831

Allison did a great job! She was wonderful with making sure all the details were squared away before we left (like double checking about where we'd want her to sleep for staying over and making sure she knew where everything was for them). And, she was good with providing updates! They all looked great when we got home. Thanks!!

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Kateland H.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$65
per night
5.0 out of 5 stars
58 reviews
15 repeat clients
15 years of experience
Chester, VA, 23831

I highly recommend Sabrina! She watched my Great Dane, Banks, and stayed at my home for five days, and I couldn’t have been happier with the experience. This was my first time leaving Banks and my house with a pet sitter, so I was a little nervous, but Sabrina quickly put me at ease. She sent multiple pictures and updates every day, which was incredibly reassuring and allowed me to relax and enjoy my trip knowing Banks was happy and well cared for. She also took excellent care of my home—it looked exactly as I had left it when I returned. Banks was happy, the house was spotless, and everything went seamlessly. I would absolutely trust Sabrina with Banks and my home again and hope to rebook her for future trips. Highly recommend!

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Chloe H.
Sitter Profile Image: Meghan T.
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Meghan T.
from
$60
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
20 years of experience
Chester, VA, 23831

Meghan was such a pleasure to work with. She gave our senior dog the time and attention he deserved and brought out his playful inner puppy. She was great at communicating and we will definitely rebook with her soon!

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Megan A.
Sitter Profile Image: Crystal A.
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Crystal A.
from
$63
per night
5.0 out of 5 stars
13 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: Jennifer Z.
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Jennifer Z.
from
$40
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
8 years of experience
North Chesterfield, VA, 23234

Jenni was a great choice to watch our fur baby overnight because of a last minute trip my partner & I had to take for a funeral. Due to our unexpected time constraint beforehand, she came over the same day of the booking and met our dog Hank & learned his routine. While we were away, she sent lots of pictures & gave us updates every so often so we were always in the know. We would definitely have Jenni watch Hank again in the future and highly recommend her for the pet sitting needs of other folks too!

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Peter C.
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: Meghan H.
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Meghan H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
20 reviews
6 repeat clients
4 years of experience
Richmond, VA, 23234

Meghan did a great job with my dog and cat for a weekend stay. Took awesome care of the house and the animals are happy. Would highly recommend.

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Matt B.
Sitter Profile Image: Melanie C.
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Melanie C.
from
$65
per night
4.7 out of 5 stars
28 reviews
4 repeat clients
17 years of experience
Richmond, VA, 23237

I can’t say enough great things about Melanie! She took such amazing care of my Frenchie while I was away. From the moment we met, I could tell she genuinely loves dogs and knew exactly how to handle my pup’s quirky personality and needs. I received regular updates, photos, and videos, which totally put my mind at ease. My Frenchie came back happy, relaxed, and maybe even a little spoiled—in the best way! I’m so grateful for the love and attention they gave. I’ll absolutely be booking with them again!

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Omead S.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$45
per night
5.0 out of 5 stars
3 reviews
1 repeat client
5 years of experience
Chester, VA, 23836

We are so grateful for Isaiah! We had to leave town last minute, and he worked with us every step of the way. He came by beforehand to meet our dogs and has a lot of experience. One of our dogs is a new adoption, and she really only likes me, but he was able to get her to a place where she was comfortable and not stressed around him. That alone says a lot about how good he is. He was accommodating to whatever we needed during the sit and was respectful of our home. When we got back, our pets were happy, relaxed, and acting completely like themselves. We’ve had experiences in the past where you could immediately tell the level of care they received, and this was the opposite. It truly felt like they had been cared for the way we would care for them. Isaiah was that person. We will definitely be reaching out to him again in the future.

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Brienia B.
Sitter Profile Image: Joseph W.
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Joseph W.
Star Sitter
from
$40
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
5 years of experience
Chester, VA, 23836

First time house sitting for our Bernedoodle and she was well handled by Joey. He took well care of her as usual, played, walked her and gave her medicine. 👍

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James K.
Sitter Profile Image: Candice D.
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Candice D.
from
$60
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
25 years of experience
North Chesterfield, VA, 23237

Candice accommodated my reactive Aussie who is very distrusting of new people. She gave her space and let my doggo make all the moves which I really appreciate. She’s been communicative the whole time and sent pictures! I will definitely be using her again now that my dog has built some trust with her.

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Jamie K.
Sitter Profile Image: Rangeen A.
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Rangeen A.
from
$95
per night
4.9 out of 5 stars
42 reviews
12 repeat clients
10 years of experience
Richmond, VA, 23237

Rangeen was great! This was my first time using a house sitter from Rover and it went perfectly! Rangeen sent me pictures and updates and how my pup was doing and was super responsive and professional. Would 100% recommend!

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Taylor R.
Sitter Profile Image: Michelle C.
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Michelle C.
from
$60
per night
5.0 out of 5 stars
10 reviews
1 repeat client
10 years of experience
Midlothian, VA, 23832

Michelle was great to work with! She was very communicative, sent lots of pictures, and took amazing care of the house. We came home to two very happy and well cared for doggies :)

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Katie O.
Sitter Profile Image: Monique & Daniel V.
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Monique & Daniel V.
from
$50
per night
5.0 out of 5 stars
54 reviews
23 repeat clients
18 years of experience
Petersburg, VA, 23803

Monique’s and her husband Daniel do an amazing job taking care of our Vizsla Skye! We have hired them many times and feel so comfortable leaving Skye in their care. Skye recently tore her ACL and we knew that she was in great hands. From the moment that we met Monique and Daniel we knew we found a great team.

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Amy D.
Sitter Profile Image: Layla H.
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Layla H.
from
$28
per night
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: Oli L.
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Oli L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
112 reviews
35 repeat clients
18 years of experience
Hopewell, VA, 23860

Oli was wonderful! We have a reactive dog who is nervous meeting new people but she warmed up to Oli quickly. Oli checked in often with photos of the pups and left everything in good order.

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Sarah K.
Sitter Profile Image: Nicole R.
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Nicole R.
from
$30
per night
1 repeat client
15 years of experience
Chester, VA, 23831

About: I am very familiar with all types of dogs! I grew up with german shepherds and most recently have fostered a Great Pyrenees. I live a very active lifestyle and am looking to go on lots of walks with your fur baby! I love giving lots of attention and ensuring interactive time with the animals in my care. Use this link for $40 off your first Rover booking!!: https://www.rover.com/sit/nicolr34569 I'm currently working part-time and have a lot of time, especially during the day, to look after your pet(s). Just give me a heads up what your request is so I can take a look at my schedule. I can go on long or short walks (I prefer longer!) I will provide a safe environment and ensure your pet's needs are more than just met.

Sitter Profile Image: Jordan D.
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Jordan D.
from
$40
per night
5.0 out of 5 stars
15 reviews
2 repeat clients
10 years of experience
Chesterfield, VA, 23832

Jordan was amazing! This was our first time using Rover and we were a little nervous but our fears were unfounded! Jordan stayed in contact through the whole stay and our pups were very comfortable with her. She did an amazing job with both our 4 month old puppy who can be a bit of a terror and our 8 year old beagle. Will definitely be using her in the future!

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Chris H.
Sitter Profile Image: Hana J.
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Hana J.
from
$75
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
17 years of experience
Colonial Heights, VA, 23834

Hana was an excellent sitter! She is very easy going and my pup instantly connected with her. She also communicated very well when I did a check-in! I will definitely be using her services again!

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Anthony G.
Sitter Profile Image: Tyeir D.
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Tyeir D.
from
$35
per night
5.0 out of 5 stars
1 review
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.

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

Pet parents share their Rover experiences - Chester

1 / 1
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

We were very happy with Meghan. We liked her bio and thought she sounded like the perfect person to care for our pets and home. She stayed in our home for a few days while we were away. She kept our home perfect and the animals loved her too. She sent pictures daily. We are so glad to have found Meghan and trust her with the care of our cat and dog.

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Jennie M.
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

Rebecca was an absolutely wonderful sitter for our pups! She was incredibly attentive, made sure all of their needs were met, and gave them so much love and care. Our dogs can be a bit high-energy and challenging at times, but she handled them with ease and confidence. From brushing them to bringing them toys and treats, Rebecca went above and beyond to make sure they felt happy, comfortable, and loved while we were away. It was clear that she genuinely cared for them and treated them like her own. We couldn’t have asked for a better sitter and would highly recommend her to anyone looking for exceptional pet care!

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Mackenzie E.
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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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 for House Sitting in Chester on Rover is $49.95 per night (as of September 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 September 2026, there are 1,460 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 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 Chester. On Rover:

  • 95% of sitters can help with special care needs
  • 97% 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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