House Sitting Chester

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

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Over 83
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
215 reviews
60 repeat clients
10 years of experience
Chester, VA, 23831

Allison was great and extremely professional. She took as good of care of our doggos as we do! She gave great updates daily with pics! 10/10 would recommend and will be using her again.

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Josh S.
Sitter Profile Image: sabrina s.
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sabrina s.
Star Sitter
from
$65
per night
5.0 out of 5 stars
54 reviews
14 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

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.
Sitter Profile Image: Sarah I.
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Sarah I.
from
$35
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
7 years of experience
Chesterfield, VA, 23832

Sarah has house sit/dog sit for us twice now and is absolutely amazing! She keeps us updated, sends pics, and makes sure the house is just as clean as we left it! Plus our fur babies loooovvveee her! We highly recommend hiring her! Thanks again Sarah!!!!

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Lidia W.
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: Crystal A.
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Crystal A.
from
$63
per night
5.0 out of 5 stars
12 reviews
10 years of experience
Chester, VA, 23831

"I cannot recommend Crystal enough! She took wonderful care of our dog Rigby and our home while we were away — the house was spotless when we got back. Crystal provided regular updates, photos, and even videos so we never had to worry. Our flight got in late and she happily stayed later to make sure Rigby was taken care of. She's responsive, kind, and clearly loves what she does. We'll definitely be booking her again!

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Chris M.
Sitter Profile Image: Samantha B.
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Samantha B.
from
$60
per night
5.0 out of 5 stars
32 reviews
17 repeat clients
30 years of experience
Chester, VA, 23831

Samantha took AMAZING care of our babies and our home. She sent lots of updates and photos giving us peace of mind. Our very shy cat even came out to get cuddles with Samantha. She left our house so clean as well! She made us some special homemade popcorn as a coming home gift. A very thoughtful added touch.we will definitely use Samantha again when we travel.

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Jennifer G.
Sitter Profile Image: Meghan H.
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Meghan H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
18 reviews
6 repeat clients
4 years of experience
Richmond, VA, 23234

Meghan was communicative throughout our trip, sent plenty of pictures and updates, and gave us peace of mind while we were away. We really appreciated that she took the time to do a meet and greet beforehand so we could go over expectations and show her around. We would absolutely recommend her to anyone looking for a reliable house or dog sitter!

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Meredith J.
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: Allyson B.
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Allyson B.
from
$40
per night
4.8 out of 5 stars
58 reviews
17 repeat clients
15 years of experience
Henrico, VA, 23231

Allyson was responsive and always sent pictures and updates while we were away, which put my mind at ease! My dog and cat seemed very happy and calm with her care, and everything with our home was in order / clean upon our return. Would use Allyson again to watch our fur babies!

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Emma W.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$40
per night
5.0 out of 5 stars
2 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: Oli L.
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Oli L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
109 reviews
35 repeat clients
18 years of experience
Hopewell, VA, 23860

We have found our forever pet sitter! Oli was there for my husband and I as we welcomed our son into this world (a week early!) and the comfort she provided by taking such diligent care of our pets was invaluable. Oli is kind, organized and genuinely loving towards animals.

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Emma H.
Sitter Profile Image: Stephenie S.
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Stephenie S.
from
$50
per night
5.0 out of 5 stars
2 reviews
30 years of experience
Chesterfield, VA, 23832

Stephenie stayed with our dogs at our house over the weekend, and she was phenomenal! We received lots of updates and happy pictures of the dogs while we were gone that helped put us at ease knowing the dogs were being well taken care of. Stephanie also maintained their routine and gave them their daily medicines. We are so happy to have met Stephenie and will be booking with her again!

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Alex 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: Michelle C.
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Michelle C.
from
$60
per night
5.0 out of 5 stars
9 reviews
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: Lashell D.
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Lashell D.
from
$112
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
15 years of experience
Chester, VA, 23831

About: Hello everyone, Put code LASHED02561 in promotion box for an immediate redemption of $20 off your first booking with me. Or use this link https://www.rover.com/sit/lashed02561 I’m an animal whisperer with over 15 years of experience, skilled in creating tailored training techniques for various dog breeds. My compassionate methods prioritize positive reinforcement, ensuring each dog feels understood. My rates reflect the quality of care I provide, including training, evaluations, and ongoing support to strengthen your bond with your pet. As a passionate pet sitter, I also offer dedicated care for dogs, cats, and small critters, customizing my services to meet their unique needs. I take pride in being a trusted name in the pet sitting industry. If you’re seeking a committed pet sitter who loves animals, I would be honored to care for your furry family members. Flexibility and Availability: Working from home and being available seven days a week allows me to accommodate various booking requests. I can offer day care services for a few hours or provide care for extended periods, such as up to two weeks. Same-day bookings can be accepted. As a Professional Pet Care Specialist, I approach each canine companion with equal attention and dedication. I provide personalized care, ensuring that every pup receives the utmost love, care, and adherence to any specific instructions provided by their owners. I recognize and respect the uniqueness of each dog, understanding that their individual needs and preferences may vary. Rest assured that I am committed to delivering exceptional care and creating a nurturing environment for your beloved furry friend. Thank you for entrusting their well-being to me.

Sitter Profile Image: Linda A.
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Linda A.
from
$65
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
30 years of experience
Chester, VA, 23831

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.
Sitter Profile Image: Triston N.
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Triston N.
from
$45
per night
5.0 out of 5 stars
9 reviews
10 years of experience
Fulton, Richmond, VA, 23231

Triston was incredible! We had to book last minute and Triston stepped up to take care of our 2 dogs and 4 cats! I will definitely be booking with Triston in the future!!

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Taylor B.
Sitter Profile Image: Anslee P.
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Anslee P.
from
$60
per night
4.9 out of 5 stars
56 reviews
17 repeat clients
15 years of experience
Chester, VA, 23831

Anslee was available and communicated with us she is the best, we will continue to have her sit our dogs

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Darcel D.
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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 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 1,448 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:

  • 94% 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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