House Sitting in Chesterfield

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

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Top rated Chesterfield house sitters

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: sabrina s.
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sabrina s.
Star Sitter
from
$65
per night
5.0 out of 5 stars
40 reviews
10 repeat clients
15 years of experience
Chester, VA, 23831

Great responsiveness and communication. My pup enjoyed her!

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Jo C.
Sitter Profile Image: Jordan D.
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Jordan D.
from
$40
per night
5.0 out of 5 stars
13 reviews
1 repeat client
10 years of experience
Chesterfield, VA, 23832

Best house and dog sitter yet! Plenty of updates, communication, photos and videos. Jordan took great care of Jet, giving him plenty of activity and affection, and our home as well. Will absolutely work with her again.

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Sam P.
Sitter Profile Image: Cassidy R.
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Cassidy R.
from
$45
per night
5.0 out of 5 stars
26 reviews
12 repeat clients
25 years of experience
Chester, VA, 23831

Cassidy was everything I’ve ever wanted in a dog sitter! Loved on my babies and communicated with me so well. Left my house in perfect condition!

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Brooke D.
Sitter Profile Image: Sarah I.
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Sarah I.
from
$35
per night
5.0 out of 5 stars
5 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: Meghan T.
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Meghan T.
Star Sitter
from
$40
per night
5.0 out of 5 stars
14 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: Crystal A.
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Crystal A.
from
$63
per night
10 years of experience
Chester, VA, 23831

About: I have taken care of dogs ranging from 10 pounds to 110 pounds my entire life. I have owned chihuahua dachshund mix, akitas, huskies, and German shepherds; so I understand big breeds as well as smaller ones. I have helped family members and neighbors with their dogs growing up with house sitting and dog walking. I know how important furbabies are to families, and treat each and every one as I would my own. I currently work full time with every other Monday off. I go to work about 7 am and get home about 430 pm. I do have volleyball leagues on Monday Wednesday and Friday nights that I am gone for 2 hours between 6-11pm as it varies based on game time. I love to hike and be outside so taking the dogs for walks a non issue. I have a small yard. It is in the process of getting fenced. If your furbaby needs to be crated that’s ok as well. They will be able to free roam if they are not crate trained. I adjust my schedule accordingly to accommodate the animals as best as I can. I have given insulin shots and medication to animals and am comfortable with it.

Sitter Profile Image: Michelle C.
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Michelle C.
from
$60
per night
5.0 out of 5 stars
6 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: Kiara P.
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Kiara P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
240 reviews
65 repeat clients
4 years of experience
Richmond, VA, 23236

Kiara is a great listener, which is a big key to success for making friends with my shy hound. Her updates are detailed, and her photos are informative (and cute!). I went on a week's trip with confidence my pets would be cared for, and they were cared for very well. The most successful part of the experience is that my shy dog was confident and happy when I returned, and I cannot express how wonderful that is. I will call Kiara for our next trip!

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

Great communication, extremely trustworthy to open your home to! We got pictures and our three dogs loved her! Definitely plan to use her in the future!

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Andi L.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$60
per night
5.0 out of 5 stars
38 reviews
19 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: Mary M.
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Mary M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
6 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: Miranda J.
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Miranda J.
from
$50
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
15 years of experience
Richmond, VA, 23234

I can’t say enough good things about Miranda. It’s clear she has a real knack for animals; my two dogs were so happy and well-exercised under her care. She was reliable, on time, and made sure everything ran smoothly. We’ve definitely found our go-to sitter and will be using her from now on!

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Mike M.
Sitter Profile Image: Journei F.
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Journei F.
Star Sitter
from
$28
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
7 years of experience
Richmond, VA, 23234

10/10

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Matt W.
Sitter Profile Image: Dianne B.
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Dianne B.
from
$65
per night
4.7 out of 5 stars
58 reviews
15 repeat clients
42 years of experience
Midlothian, VA, 23112

Dianne is my hero. She stepped in at late notice and took care of our pack with minimal instructions, minimal contact from me, and with the internet unexpectedly down and still took amazing care of our whole menagerie. We were not an easy client but she stepped in and totally made it look easy taking care of four dogs, a snake, a bearded dragon, and a betta. Dianne knows what she’s doing.

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Samantha T.
Sitter Profile Image: Peyton B.
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Peyton B.
from
$28
per night
20 years of experience
Jackson Ward, Midlothian, VA, 23112

About: Growing up my family always had at least one or more pets of various breeds so I have 20+ years of experience around animals. I have cared for dogs, cats, fish, lizards, rabbits, goats, and hedgehogs. Personally, my husband & I have 2 dogs currently, 9 & 10 years old, one having epilepsy & is dependent on medication. I have helped raise/care for/train puppies, kittens, baby rabbits, & baby goats. The only pet I'm not comfortable with is snakes, my little sister has one but I only look at it from 3ft away in its enclosure, haha. I work part time Tu/W/Th 8A - 5P, I do not mind caring for pets those days, however I will be gone all day. Otherwise, I'm available for your pets needs! My personal routine with my pets: My husband helps me care for our pets daily but his schedule is a bit different than mine, so our dogs are let out at least within 4-6 hours those days. Otherwise, we let them out every 2-4 depending on their needs (which they have been trained to lets us know if they need to go sooner). Our medical dog is on a 12 hr medication schedule. I'd prefer to care in my clients home due to one of my dogs having a reactive past, it was quite a transition when we inherited our other dog. If you have a specific routine, I'm ready to follow it to the T! I'm comfortable walking dogs on leash, hanging out/playing with them in a fenced yard, or just chilling inside. As mentioned, I have experience with medically dependent pets. I have an escape artist, so I'm always vigilant of their proximity to me and prepared to run/chase in the event something happens. I can stay at the home with the pets or I can visit throughout the day!

Sitter Profile Image: Savannah B.
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Savannah B.
from
$28
per night
15 years of experience
Shockoe Slip, Richmond, VA, 23219

About: I’ve been an animal lover my whole life and have experience caring for both dogs and cats of all ages, sizes, and personalities. Growing up with pets taught me how important patience, consistency, and affection are when it comes to quality pet care. When I was younger, I even helped train my childhood dog, which taught me responsibility, positive reinforcement, and how to understand animal behavior from an early age. I’m comfortable with feeding routines, walks, playtime, and making sure pets feel safe and loved while their owners are away. As a teacher, I’m dependable, attentive, and patient, and I truly enjoy spending time outdoors going on walks and staying active with pets. My goal is always to make your pet feel happy, comfortable, and cared for like family. As a teacher currently on summer break, I have a very flexible schedule and plenty of availability for pet care throughout the day. I’m able to dedicate extra time and attention to walks, drop-ins, playtime, and maintaining pets’ routines. Pet care fits naturally into my schedule because I genuinely enjoy staying active, spending time outdoors, and caring for animals. I love being able to use my summer break doing something rewarding while giving pets the attention, companionship, and care they deserve. Safety, trust, and creating a comfortable environment are my top priorities as a pet sitter and walker. I understand that pets are family, and I treat every animal with patience, kindness, and close attention to their individual needs and routines. I always prioritize safe walks, secure environments, and clear communication with owners so they feel confident their pets are in good hands. I’m dependable, responsible, and attentive, which helps me build trust quickly with both pets and their owners. My goal is to create a calm, caring environment where pets feel safe, happy, and loved while you’re away.

Sitter Profile Image: Mia M.
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Mia M.
from
$40
per night
10 years of experience
Chester, VA, 23831

About: Animals have been a massive part of my life for as long as I can remember, and growing up in a household with both dogs and cats taught me how to read their unique body language and personalities. Today, I am a proud pet parent to two wonderful cats of my own, so I know firsthand just how much your pets mean to you and the level of care they deserve. I have hands-on experience handling pets of all shapes, sizes, and ages, which includes raising a family dog from a puppy and training him to sit, as well as managing and pet-sitting two energetic 80-pound dogs simultaneously. I am also entirely comfortable with the less glamorous sides of pet care, as I am highly experienced in administering oral pills and various medications to both cats and dogs, maintaining strict routines, and handling unexpected bathroom accidents or cleanups calmly and thoroughly. I work full-time Monday through Friday, making my daytime availability perfect for early morning or evening walks, check-ins, and feeding routines. I am also available for overnight housesitting during the week, though this is typically best suited for independent adult animals who are comfortable being alone during standard work hours. My weekends are completely open and flexible for overnight care, extended daytime sitting, and drop-ins. Because young puppies require constant, round-the-clock supervision and undivided attention, I only accept puppy-sitting bookings strictly on Saturdays and Sundays to ensure your little one gets the dedicated care they need. Building a foundation of trust is my top priority when entering your home to care for your pets. For dogs, this means maintaining strict leash safety during walks, keeping a watchful eye for hazards, and following their established feeding and bathroom routines to minimize any anxiety. For cats, I prioritize a calm, respectful environment, giving them the space they need to feel secure while ensuring litter boxes are pristine and food is fresh. I treat your home with the utmost respect—keeping it clean, locking up securely, and handling unexpected messes or accidents quickly and thoroughly. Whether keeping a energetic dog safe on a walk or administering medication to a sensitive cat, I am committed to providing a secure, stress-free environment so you can have total peace of mind while you are away.

Sitter Profile Image: Hannah T.
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Hannah T.
from
$45
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Midlothian, VA, 23112

Hannah was a wonderful and caring pet sitter/house sitter. We have a much older dog that requires some medical needs and Hannah put us at ease that he would be cared for while we were away. Hannah communicated multiple times a day, sent pictures and asked questions if she was concerned about our dog's behavior. Hannah was very respectful of our home while she stayed. We were able to enjoy time away thanks to Hannah's care of our dog. We will definitely rebook with Hannah!

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hannah c.
Sitter Profile Image: Miles G.
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Miles G.
from
$45
per night
5.0 out of 5 stars
5 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: Ada C.
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Ada C.
from
$60
per night
4.9 out of 5 stars
17 reviews
4 repeat clients
4 years of experience
Richmond, VA, 23236

Ada stayed overnight at my house with Bailey. She did an excellent job. Bailey loved her. She walked Bailey in the neighborhood and cuddled with her...No wonder Bailey loves her. She also left my house very nice and clean after staying there for 5 days. I will definitely call her again when Bailey needs a sitter.

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marolyn s.
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Over 314
pet parents in Chesterfield have booked house sitting

Chesterfield pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

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.
House Sitting
5.0 out of 5 stars

Phyllis is the best! A++++++ We booked a house/pet sitting service for our Christmas vacation back in July to prepare our dog for our trip and to be with a new person. Phyllis had some meet and greet visits and some walks before our vacation and Harley warmed up to her really quickly. She sent so many messages and wonderful pictures of Harley (dog), Oliver (cat), and the fish. She is so wonderful and we will be using her for walks for our dog and any trips we have in the future. I just hope she doesn’t get too popular and we can’t get her again. Thank you so much for everything.

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Kristina F.
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
5.0 out of 5 stars

Rangeen is a true dog lover. My dog slept with her and doesn't sleep with me! He was in good spirits when I got home. Rangeen sent regular photos and updates. Will book with her again!

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Fran T.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

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 house 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.

Sitters in Chesterfield average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chesterfield on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Chesterfield house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,380 house sitters in Chesterfield. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Chesterfield house sitters respond in under an hour.

House sitters in Chesterfield have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Chesterfield.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chesterfield house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.