House Sitting Chestnut Grove

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

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Over 10
pet parents in Chestnut Grove have booked house sitting

Chestnut Grove, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 15% and taxes will apply.

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Sitter Profile Image: Danielle C.
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Danielle C.
Star Sitter
from
$80
per night
5.0 out of 5 stars
• 275 reviews
79 repeat clients
30 years of experience
Charlottesville, VA, 22901

“Danielle was great with the pups - kind, attentive, courteous and communicative. She took great of the house And my pups. I’d definitely book with her again.”

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Emily & Stuart B.
Sitter Profile Image: Maddie K.
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Maddie K.
from
$50
per night
5.0 out of 5 stars
• 34 reviews
10 repeat clients
8 years of experience
Charlottesville, VA, 22901

“I am so grateful to have found Maddie! She is responsible, communicative, and loves our pets! Leaving our cat and senior dog can feel so hard but I felt very comfortable with Maddie. We will definitely ask her to watch them again”

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Tara H.
Sitter Profile Image: Abigail J.
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Abigail J.
from
$65
per night
4.7 out of 5 stars
• 16 reviews
5 repeat clients
40 years of experience
Charlottesville, VA, 22901

“My fiancée and I feel like we’ve hit the jackpot after adding Abi to our lives! She came to our home before our trip to meet us and our girls, ask plenty of questions, and see how the dogs responded to her presence. She is warm and patient, and even our super anxious/epileptic dog took to her quickly (a rare occurrence). She was meticulous in reviewing our care instructions for our needy crew (two dogs on several meds). She texted us pictures while we were away, asked follow up questions, and truly put our minds at ease seeing how much she cared for our girls. We can’t thank her enough for the ways she impressed us, and hope to have her return soon!”

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Courtney P.
Sitter Profile Image: Mary B.
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Mary B.
from
$36
per night
4.9 out of 5 stars
• 58 reviews
21 repeat clients
11 years of experience
Barboursville, VA, 22923

“Mary was responsive, punctual, and took good care of our Bella and house. She sent us updates and pictures and Bella was happy and content upon our arrival. We will definitely consider booking Mary again if the need arises. Thank you, Mary, for fitting us in during this busy holiday season!”

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Regina H.
Sitter Profile Image: Gavin D.
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Gavin D.
Star Sitter
from
$100
per night
5.0 out of 5 stars
• 4 reviews
5 repeat clients
1 year of experience
Charlottesville, VA, 22901

“Gavin was the best! Super detail oriented and brought his own checklist to go over during our meet and greet so he wouldn’t miss anything. He was very flexible and communicative, and even left a very sweet thank you card at the end of his visit. Would definitely recommend his services to anyone else looking for a sitter!”

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Cheyenne G.
Sitter Profile Image: Kelly H.
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Kelly H.
from
$75
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
40 years of experience
Ruckersville, VA, 22968

About: I have had dogs and cats as long as I can remember and absolutely love them and have taken care of friends' dogs for years house sitting for them many years. I have worked with horses for may years as well in many different stables, barns, rescue organizations and also therapeutic riding centers. I have helped many friends and neighbors over the years with sitting for their pets while they travel for business or vacation. I have owned dogs since I was a little girl and even rescued one in my neighborhood when I was little and named him Brownie as he was all white and had one brown spot on him. We were inseparable! Sassy was also my best friend when I was living in Virginia and I never left her when I went on vacation and always took her with me. We ran every morning, played soccer, frisbee, and she loved the beach and was such a good swimmer that she loved to ride the waves. I miss her every day! I also horse sit as I have 16 years experience working with horses on farms, equestrian facilities, rescue and SPCA facilities and therapeutic riding organizations so I can take cares of your horses too🐎🦋 I have just moved back to the Charlottesville area where I am originally from. I love to be with animals and would love to help take care of yours having taken care of dogs, cats, horses for many years for friends and their friends 😀I am so responsible, dependable, loving, kind, and your pets would be so pampered and cared for that you would have no worries about them while you are away 😍I have wonderful referrals from my many years of pet sitting and working with horses. I would love to take care of your “kids”. I love to walk and would take your dogs for lots of walks as well as plenty of playtime and snuggle time😄they would have lots and lots of attention 😁😁

Sitter Profile Image: Lauren O.
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Lauren O.
from
$60
per night
1 repeat client
10 years of experience
Charlottesville, VA, 22903

About: I have been taking care of neighbors' dogs since I was nine years old! I have watched many senior dogs and dogs with special routines. I'm currently working on my Master's in Public Health at UVA, so I have plenty of flexibility to keep your dogs company! I am available most weekday evenings and weekends! Happy to care for your dogs however you prefer! Whether that means chill nights and short walks or longer hikes, I am happy to meet the needs of each individual pup. Just let me know what works for you and your family:)

Sitter Profile Image: Maire F.
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Maire F.
from
$20
per night
6 years of experience
Main-Starr Hill, Charlottesville, VA, 22903

About: I’ve grown up around animals my entire life, with 2 dogs and 2 cats since I was 3 years old. Caring for animals has always been a huge part of my life, and I genuinely love getting to know each pet’s personality and needs. I’m patient, attentive, and comfortable with animals of different ages and temperaments. I’ve even dreamed of owning an animal shelter one day! I’ll treat your pets with the same care, attention, and affection I would give my own. Starting in mid-May, I’ll have a very flexible schedule and will be available for pet care throughout the week. I’ll likely have another part-time job, but I’ll be able to work my schedule around pet-sitting and make sure I have plenty of time to give each pet the attention and care they need. I’m especially interested in regular or recurring pet-care opportunities and am happy to accommodate different schedules and routines. When house sitting, I treat both your pets and your home with the same care and respect I would want someone to give my own. I’ll follow your pet’s normal routine as closely as possible, including feeding, walks, medication if needed, and plenty of attention and playtime. I’m also very respectful of your space and will keep your home clean and secure while you’re away. My priority is making sure your pets feel comfortable, safe, and cared for in their own environment, so you can have peace of mind while you’re gone.

Sitter Profile Image: Emil F.
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Emil F.
from
$27
per night
4.7 out of 5 stars
• 66 reviews
29 repeat clients
10 years of experience
Charlottesville, VA, 22901

“Emil was very accommodating and kind. He communicates very well. Our dog, Zeus, did very well at his home. He seemed to like Emil and had no issues. Thanks again for being available on short notice!”

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Jennifer Z.
Sitter Profile Image: Anna D.
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Anna D.
Star Sitter
from
$25
per night
5.0 out of 5 stars
• 16 reviews
8 repeat clients
17 years of experience
Belmont, Charlottesville, VA, 22902

“Anna was great! She took great care of my dog and my place while I was gone! She communicates well, sends frequent updates. Will rebook with her in the future!”

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Jaelyn C.
Sitter Profile Image: Brooklyn M.
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Brooklyn M.
from
$60
per night
5.0 out of 5 stars
• 4 reviews
13 years of experience
Main-Starr Hill, Charlottesville, VA, 22903

“Brooklyn pet-sat for my two dogs and took great care of them. She is super friendly and communicative, and we were able to enjoy our time away without any worries.”

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Katja S.
Sitter Profile Image: Melissa H.
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Melissa H.
from
$60
per night
4.8 out of 5 stars
• 12 reviews
3 repeat clients
15 years of experience
Charlottesville, VA, 22911

“We were so pleased with Melissa’s stay with our pets. She is reliable, communicated well with us while we were away by sending photos and updates. We also appreciated her flexibility when our travel plans changed last minute. We came home to happy dogs and a well kept home!”

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Kt G.
Sitter Profile Image: Courtney C.
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Courtney C.
from
$65
per night
10 years of experience
Charlottesville, VA, 22901

About: I’ve always loved animals and have experience caring for a wide variety of pets, including dogs, cats, fish, hamsters, hermit crabs, and more. As a pet owner myself, I understand how important it is to feel confident and comfortable leaving your pets in someone else’s care. I’m responsible, detail-oriented, and attentive to each pet’s individual needs and routine. I’d love the opportunity to get to know you and your pets and provide them with the same care and attention I’d want for my own. I work as a swim coach currently so I’m looking for supplemental work, but I am decently flexible and can make time multiple times throughout the day to care for your animals! I am very responsible and understand that your pet is like an extension of family. I have two cats of my own & they are like my children. I pride myself in creating a safe, loving, & playful environment for your pet!

Sitter Profile Image: Tiffanie F.
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Tiffanie F.
from
$60
per night
5.0 out of 5 stars
• 27 reviews
7 repeat clients
30 years of experience
Waynesboro, VA, 22980

“Tiffanie was great. Even though last minute, she came to meet the dogs before her stay. She took great care of them, sent lots of pictures, was very communicative-commenting on each dog’s personality so you know that she’s spending time with them, and left our house in perfect condition.”

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Amy S.
Sitter Profile Image: Emma D.
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Emma D.
from
$34
per night
5.0 out of 5 stars
• 2 reviews
5 years of experience
Waynesboro, VA, 22980

“Emma did such a great job with our two pups! She sent plenty of updates and photos during her stay and we came home to a clean house and some happy dogs. I would definitely recommend her!”

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Marissa B.
Sitter Profile Image: Moira R.
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Moira R.
from
$60
per night
30 years of experience
Massanutten, VA, 22801

About: I have owned and cared for many dogs throughout my life. I love every single one of them, including puppies. Active walker and play as desired. I work one day remotely (flexible day choice --weekends and holiday available! I can check on them at lunch if more than weekend is needed. Fenced yard, welcome your crate if your dog is used to it, lots of toys, blankets, and great area for walks. I provide a fun, safe environment for dogs to interact with others.

Sitter Profile Image: Nicole P.
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Nicole P.
from
$40
per night
5.0 out of 5 stars
• 1 review
1 repeat client
10 years of experience
Madison, VA, 22727

About: Animals definitely perceive my positive attitude, and people do too. I genuinely love making cats and dogs happy. I often talk to any animal quite a bit because I believe a calm tone of voice is good for them psychologically. Additionally, I have taken care of multiple dogs and cats throughout the years, working in kennel facilities and through ownership, and I understand what is required to keep them happy and healthy. I have a flexible schedule, with much time to ensure your pets get the exercise he or she needs, and the attention they deserve. They won't be lonely while you're away! Additionally, I can administer any medications necessary and follow any special dietary restrictions. Your cats and dogs are in good hands with me! I center taking care of my own animals around my daily schedule. I do my best to keep their regular feeding times ,and for my dogs walking times at expected hours. It can be difficult, but it wouldn't be fair for them to not know what to expect. So ultimately, I adjust my required needs around their schedule in terms of errands, and etcetera. I care for pets in a way they are accustomed to; meaning regular schedules for feeding, walks and/or medication. If they are staying in my home, I would try to provide the most comfortable accommodations as possible while awaiting their people. But in a client's home, I would just coddle the pet, give them comfort, and again - keep them on the schedule they are accustomed to.

Sitter Profile Image: Samantha K.
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Samantha K.
from
$175
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
20 years of experience
Heards, VA, 22931

About: I am comfortable with all kinds of dogs and needs. I personally care for a GSD and a Heeler mix, and am comfortable with rambunctious and large dogs. Both of my dogs practice loose leash walking, and I love using our walks as time to tire their brains as well as their bodies. I can give medications, including subq and other injections. And I’m working on becoming a certified trainer, but for now I do not offer training services. I work a few part time gigs that change with the seasons. I have lots of flexibility to meet the needs of your pets. I generally do not go out of town during major holidays. I have lived on estates as a property manager, and ran my own home repair business for several years. I’m good at handling emergencies, and enjoy fixing things when I have the opportunity

Sitter Profile Image: Tina P.
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Tina P.
from
$60
per night
5.0 out of 5 stars
• 36 reviews
11 repeat clients
20 years of experience
Scottsville, VA, 24590

“Tina was wonderful with our puppy. He had never had a pet sitter before, and she took excellent and loving care of him, with lots of play time, exercise, and even some training. He even cried when she left! We will definitely ask her to take care of him again.”

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Carolyn C.
Sitter Profile Image: Kathy M.
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Kathy M.
from
$50
per night
5 years of experience
Harrisonburg, VA, 22801

About: Hello. I’m Kat, and I am an experienced sitter who's been taking care of homes and pets through Trusted Housesitters for nearly two years now. At this time, I have 18 recent sits under my belt. I am former membership director of a nonprofit for writers, and these days I’m traveling in my van, house/pet sitting, and working on my own writing. I love animals and grew up in the country with 14 outdoor cats and 3 different dogs. I sat for a lot of professors as a grad student and thought it would be fun to return to that as an experienced adult who has owned her own home and raised two children. As I am looking for home/pet sitting gigs, and I work from home, I have a lot of flexibility to spend time with and caring for your pets. 3-4 hours a day can be spent on pets, home, and indoor and outdoor plants, etc. I do whatever the pet owner does in their home, including cuddles, feeding, brushing, scooping, meds if needed, plus house care, and of course treats!

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The median cost per night for house sitting in Chestnut Grove is €50

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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to 25.000 € reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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  • Reservation protection

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

  • World-class support

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

How to book house sitting

  1. 1. Search

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

    Schedule a free in-person Meet & Greet to find the perfect fit.
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Popular requests for house sitting - Chestnut Grove

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Sitters in Chestnut Grove average 4
repeat house sitting clients

FAQs for House Sitting - Chestnut Grove

Frequently asked questions about Rover

The average cost of House Sitting in Chestnut Grove is $28 per night as of November 2026. Most bookings cost between $28 and $32 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 488 sitters on Rover offering House Sitting across Chestnut Grove. 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 Chestnut Grove 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 Chestnut Grove 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 Chestnut Grove 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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

  • 89% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 95% 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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