House Sitting Chesterfield

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

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Over 39
pet parents in Chesterfield have booked house sitting

Chesterfield, 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: Sarah I.
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Sarah I.
from
$35
per night
5.0 out of 5 stars
8 reviews
1 repeat client
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: sabrina s.
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sabrina s.
Star Sitter
from
$65
per night
5.0 out of 5 stars
50 reviews
14 repeat clients
15 years of experience
Chester, VA, 23831

Sabrina is such a fantastic pet sitter, a true God send! It was the first time we have ever left our boys alone with anyone and she was just fabulous!! She sent so many pictures, and kept us posted the entire time we were gone. She even took care of our lizards and fish for us. So reasonably priced and worth every penny. We will definitely be using her again and again and again!!!

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Christine D.
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: Crystal A.
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Crystal A.
from
$63
per night
5.0 out of 5 stars
11 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: 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

It was not easy leaving my dogs but I knew they were in good hands the minute I met Meghan. She took great care of my dogs and sent me detailed updates. I highly recommend Meghan and will definitely use her again!

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Kourtney D.
Sitter Profile Image: Mary M.
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Mary M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
10 years of experience
Richmond, VA, 23235

Very friendly and responsible. She took great care of my pupper and was very communicative. Would definitely work with Mary again 😊

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Becka H.
Sitter Profile Image: Kiara P.
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Kiara P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
256 reviews
71 repeat clients
4 years of experience
Richmond, VA, 23236

Kiara was wonderful! She played with our dog several times a day, bringing her outside in good weather and playing inside when it rained. Kiara kept up with the dog's medication schedule. She sent us pictures and descriptions daily, showing what our dog was up to, with several funny pictures and captions. Kiara also watered my outdoor plants -- they were in great shape when we got home -- and she was extremely considerate in terms of keeping the house in good shape. We will definitely hire her again!

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Phoebe W.
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: Journei F.
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Journei F.
Star Sitter
from
$28
per night
5.0 out of 5 stars
8 reviews
5 repeat clients
7 years of experience
Richmond, VA, 23234

10/10

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Matt W.
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 excellent! She was so good to the pups I think they were sad when we got home!! 😍 She sent so many pictures and wrote messages to us on how the dogs were doing. The house looked nice and orderly, too, when we arrived which is always wonderful to come home to. I wish I could give her wayyyyy more stars than 5!!

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Sandrea M.
Sitter Profile Image: Isaiah M.
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Isaiah M.
from
$40
per night
5.0 out of 5 stars
2 reviews
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: Ada C.
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Ada C.
from
$60
per night
4.9 out of 5 stars
18 reviews
5 repeat clients
4 years of experience
Richmond, VA, 23236

Ada house sat my dog who was both diabetic and recovering from bronchitis which required shots and other medications twice a day. She not only cared for MMO’s medical needs but provided emotional support for him in my absence. She sent pictures and conducted a River video chat with me to ensure not only Momo’s emotional support but for mine as well. I felt confident my beloved pet was in good hands.

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Mary k S.
Sitter Profile Image: Dianne B.
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Dianne B.
from
$65
per night
4.7 out of 5 stars
62 reviews
17 repeat clients
42 years of experience
Midlothian, VA, 23112

Dianne was incredible, so communicative, and super gracious dealing with some unexpected challenges while taking care of our pack. We appreciate her so much and will absolutely use her again.

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Samantha T.
Sitter Profile Image: Kristina & Richard T.
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Kristina & Richard T.
from
$45
per night
5.0 out of 5 stars
6 reviews
20 years of experience
Midlothian, VA, 23114

Kristina was very responsive, sending updates and photos of my little fur baby. Her kids were kind and gentle as well and Izzy loved getting the attention.

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Stephanie T.
Sitter Profile Image: Miles G.
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Miles G.
from
$45
per night
5.0 out of 5 stars
6 reviews
1 repeat client
2 years of experience
Mechanicsville, VA, 23111

Miles was so great with Kip. He walked him, went lots of pics and took absolutely fantastic care of our house too. Will absolutely book him again.

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Jake L.
Sitter Profile Image: Victor S.
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Victor S.
Star Sitter
from
$70
per night
4.9 out of 5 stars
33 reviews
11 repeat clients
4 years of experience
The Museum District, Richmond, VA, 23220

Victor was an exceptional guest and a wonderful caretaker for my two dogs. He followed all instructions carefully, maintained great communication while I was away, and most importantly, my dogs absolutely adored him. The house was spotless when I returned! Victor went above and beyond to ensure everything was in order, and I felt completely at ease knowing my pets and home were in such capable hands. I would not hesitate to welcome him back again. Highly recommended!

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Cole M.
Sitter Profile Image: Nathan C.
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Nathan C.
Star Sitter
from
$50
per night
4.9 out of 5 stars
10 reviews
4 repeat clients
16 years of experience
Midlothian, VA, 23113

Nathan was great, super accommodating and did very well with our pup. He handled a challenging situation and didn't have any issues taking good care of our girl.

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

Samantha is our go to when we need a petsitter. She always takes great care of our dog and cats. In addition, she is a great communicator and leaves our home in the way it was when she arrived. We highly recommend her for your petsitting needs.

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Johan K.
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

Oli was FANTASTIC to work with! She kept us updated throughout the weekend and shared adorable pics. It created such peace of mind that our dog was in great hands and allowed us enjoy our time away. I would highly recommend Oli and we plan to work with her again in the future!

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Amanda S.
Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Chester, VA, 23831

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

Pet parents share their Rover experiences - Chesterfield

1 / 1
5.0 out of 5 stars

This the first time that Crystal watched our dog and we came home to a very happy pup! I appreciated that Crystal clearly loves dogs, is a great communicator, and took great care of our pup!!!

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Erin K.
House Sitting
5.0 out of 5 stars

Sarah was a wonderful house guest and sitter for our pups! Coming home was so wonderful as the house was well kept and you could tell the dogs were well cared for. She gave us great updates while we were away and left us with clean sheets, a sweet note of things we needed to catch up on, and some well mannered pups. Would love for Sarah to sit for us again in the future!

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Taylor S.
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

The week before our trip, Rebecca came to meet Paintball and get familiar with our home and the cat care supplies and routine. Paintball can be hesitant around strangers, but they quickly became friends! While we were away, Rebecca was excellent at communicating with me and she sent us many pictures of Paintball living her best kitty cat life. She even gave her a thorough brushing! Our house was just as we left it and Paintball appeared to be well cared for while we were away :) We would be happy to use her services again in the future.

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Chrystie R.
House Sitting
5.0 out of 5 stars

Brevin was great with all 4 of our pets (3 Dogs and a Cat) and they are a handful lol. I would recommend Brevin for all your petting needs and look forward to hiring him for our next trip.

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Cooper B.
House Sitting
1 / 1
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

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

  • World-class support

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

Meet local sitters who will treat your pets like family

  1. 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

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Chesterfield

Select a filter and find qualifying sitters offering house sitting.

Sitters in Chesterfield average 4
repeat house sitting clients

FAQs for House Sitting - Chesterfield

Frequently asked questions about Rover

The average cost for House Sitting in Chesterfield on Rover is $46.62 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 1,431 sitters on Rover offering House Sitting across Chesterfield. 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 Chesterfield 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 Chesterfield 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 Chesterfield 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 Chesterfield. 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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