House Sitting in Chestnut Grove

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

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Top rated Chestnut Grove 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: Rosey Y.
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Rosey Y.
Star Sitter
from
$60
per night
5.0 out of 5 stars
59 reviews
17 repeat clients
5 years of experience
Charlottesville, VA, 22901

Rosey did an awesome job housesitting our three large, energetic dogs for five days. She has sat for us in the past, and we have always had great experiences. Our dogs love her!

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Lauren W.
Sitter Profile Image: Bertie & Lissette A.
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Bertie & Lissette A.
Star Sitter
from
$55
per night
5.0 out of 5 stars
74 reviews
30 repeat clients
16 years of experience
Charlottesville, VA, 22911

Bertie and Lissette's family were amazing! They took great care of my puppy and were very responsive and easy to communicate with. I will definitely contact them again the next time I am in Charlottesville.

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Onyx M.
Sitter Profile Image: lindsey g.
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lindsey g.
from
$58
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Ruckersville, VA, 22968

Lindsey was great at communicating with us - sending pics of her with our pups every day. House was probably cleaner when we got home than when we left, too! Our dogs seemed really happy.

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Amy E.
Sitter Profile Image: Nathan M.
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Nathan M.
from
$64
per night
5.0 out of 5 stars
30 reviews
11 repeat clients
20 years of experience
Charlottesville, VA, 22902

Our dogs fell in love with Nathan right from the start. He was great taking them out for walks, feeding them, playing ball with them, and cuddling with them. We will definitely use Nathan again!

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Tracey C.
Sitter Profile Image: Abigail J.
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Abigail J.
from
$65
per night
4.7 out of 5 stars
15 reviews
4 repeat clients
40 years of experience
Charlottesville, VA, 22901

Out of towner: Abby was amazing at watching our dog for the first time as we came to town for an event. She was so easy to communicate with and took extra great care of our dog for the night. Wish we lived closer so we could use her again!

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Ethan L.
Sitter Profile Image: Danielle C.
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Danielle C.
Star Sitter
from
$75
per night
5.0 out of 5 stars
184 reviews
59 repeat clients
30 years of experience
Fry Springs, Charlottesville, VA, 22903

Danielle was amazing at loving on our pets, keeping to their routines, and sending us updates. We look forward to using her again and again as a sitter for our fur babies!

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Brooke H.
Sitter Profile Image: Madelyn K.
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Madelyn K.
from
$50
per night
5.0 out of 5 stars
19 reviews
3 repeat clients
15 years of experience
Earlysville, VA, 22936

Madelyn did a fantastic job taking care of my two dogs, two cats, and house during a recent overnight trip, and I can recommend her without reservation. It was my first time using Rover so I wasn't quite sure what to expect, but Madelyn made it super easy. She is responsible, enthusiastic, and communicative, and it's clear she loves animals. And judging from the pics she sent, the animals had a wonderful time!

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Mike P.
Sitter Profile Image: Dakota W.
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Dakota W.
Star Sitter
from
$40
per night
4.9 out of 5 stars
87 reviews
36 repeat clients
10 years of experience
Johnson Village, Charlottesville, VA, 22903

Dakota once again took great care of our Gretzky, who has lots of dietary and medication needs. We will absolutely be using Dakota from here on out!

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Landon R.
Sitter Profile Image: dieira h.
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dieira h.
from
$25
per night
5.0 out of 5 stars
12 reviews
5 repeat clients
6 years of experience
Charlottesville, VA, 22911

Dieira has been amazing and our Izzy just adores her, she has stayed in our home do 2 plus weeks with no issues and checked in with sweet pictures regularly. We will definitely use her services again ☺️

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J D.
Sitter Profile Image: Zach D.
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Zach D.
from
$55
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
15 years of experience
Charlottesville, VA, 22901

Zach was a new sitter to our family and I am so glad we met him through Rover! He took the absolute best care of our dog and cats, and our house, while we were away for a few days. It was so nice knowing our furry family members were in great hands. He definitely treated them like his own and I have a feeling they're going to miss him now that we're home! We can't wait to have Zach back again!

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Jamie O.
Sitter Profile Image: Dawn "Star" C.
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Dawn "Star" C.
Star Sitter
from
$95
per night
4.9 out of 5 stars
124 reviews
39 repeat clients
40 years of experience
Charlottesville, VA, 22901

We had an outstanding experience with Star as our house and dog sitter. From start to finish, her professionalism, reliability, and genuine care gave us complete peace of mind while we were away. Our dog, Millie, received exceptional attention, exercise, and affection, and it was clear upon our return that she had been very well cared for. In addition, our home was maintained impeccably. Everything was in excellent order, and we truly appreciated the level of respect and responsibility shown throughout. Communication was consistent and thoughtful, with regular updates that kept us reassured. We would highly recommend Star to anyone seeking a trustworthy and dedicated house and pet sitter. Her commitment to both our pet's well-being and our home's care was exemplary, and we would not hesitate to book her services again. Without a doubt, this was our very best house sitting and dog sitting experience in our 25 years of pet ownership.

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Betsy H.
Sitter Profile Image: Ashley B.
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Ashley B.
from
$50
per night
5.0 out of 5 stars
4 reviews
10 years of experience
Charlottesville, VA, 22901

About: I’ve always had animals in my younger life from cats to dogs, and even though I only have a cat I continue to love dogs. My current housing situation allows me to share dog sitting and caring of his clients dogs (ages 9 months to 14 years) for the last ten years. Since then I have asked my neighbors for tending to the needs of their dogs be it from a 5 mile walk on and off leash to a 100 yard potty break in addition to giving medications. I’m currently working part time three days a week and an occasional Saturday, so I have the time to care and interact for your furry friend. I live in a neighborhood with easy access to the Rivanna trails and a road trip access to a farm with woods in Earlysville for running in fields. I also have a very tolerant cat who actually enjoys dogs staying with me because she’s learned that visiting dogs often get a treat she’s earned one too. My house has hardwood floors on the first floor throughout access to the carpeted lower level is through a door. The dog would have free range of the house while we were at home and unless he/she is accustomed to be crated.

Sitter Profile Image: Lindsay M.
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Lindsay M.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
8 years of experience
Charlottesville, VA, 22901

Lindsay was great with my puppy Hank! She was available last minute, flexible with my unpredictable schedule and super responsive! She followed all of my instructions and sent lots of pictures and updates. I would definitely recommend her again!

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Katie S.
Sitter Profile Image: Sterling M.
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Sterling M.
from
$65
per night
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Charlottesville, VA, 22911

Sterling was amazing with our high maintenance dog! He’s a lot and she did great with him. She sent updates and pictures every day, and left our home spotless! She is very responsive to all communication. Highly recommended.

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Jessie D.
Sitter Profile Image: Anna S.
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Anna S.
Star Sitter
from
$80
per night
5.0 out of 5 stars
11 reviews
8 repeat clients
8 years of experience
Charlottesville, VA, 22911

About: I’ve grownup with family dogs my whole life. When I was 13 I started a small dog walking business around my neighborhood. When I was 16 I got my own dog who became my best friend. When I was 18 I did an internship at a dog boarding place. I’ve had experience with all kinds of doggy personalities and can’t wait to get to know your pup! I have my own pitbull mixed dog named Coco who I care for daily. We go on adventures outside and spend a lot of time cuddling. She is the most important thing to me in the world. I care deeply for animals and I take the time to get to know each animal individually because making them feel loved and safe is my main goal. I am able to bathe, give medication, etc.. if needed. I am very comfortable with all aspects of dog care.

Sitter Profile Image: Paris A.
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Paris A.
from
$65
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Venable, Charlottesville, VA, 22903

Paris is great! Took awesome care of my dog, all with relatively short notice. :)

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Matthew C.
Sitter Profile Image: Madalyn H.
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Madalyn H.
from
$65
per night
4.6 out of 5 stars
14 reviews
1 repeat client
10 years of experience
Ruckersville, VA, 22968

Madalyn was terrific. Very communicative and put in extra effort with one of our more difficult pets. Thanks again!

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Isaac H.
Sitter Profile Image: Montana P.
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Montana P.
from
$50
per night
4.9 out of 5 stars
18 reviews
3 repeat clients
30 years of experience
Lake Monticello, VA, 22902

Montana was great! I've used her twice now and would recommend! She checks in and I know my dog is well cared for when she's there!

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Carissa B.
Sitter Profile Image: Mitch H.
Verified Enhanced Background Check
Mitch H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
58 reviews
20 repeat clients
14 years of experience
Charlottesville, VA, 22901

Definitely one of my favorite pet sitters that I have worked with since using Rover. Communicated really well throughout the stay. I got lots of picture updates. With the weather changing, he had no issue putting both dogs in sweaters. I felt so confident that they were receiving the best care possible.

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Lydia J.
Sitter Profile Image: Kyla G.
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Kyla G.
from
$27
per night
15 years of experience
Barboursville, VA, 22923

About: I have been a pet owner for over 15 years and have experience working with terminally ill cats and dogs. I also have been trained under vets both in-clinic and out of clinic. I currently work part time a couple hours with horses in barn and an Australian Shepherd. So I have ample time to spend with your fur babies at home. I am an energetic person, so I love to go for walks, spend ample time outside playing fetch and other stimulating games. I also enjoy water play if the fur babies enjoy water.

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Chestnut Grove pet parents share their Rover experiences

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5.0 out of 5 stars

Reilly did an excellent job house sitting and taking care of my three pups. I am eternally grateful and will call her first when I need future help caring for my babies!!

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Steel M.
House Sitting
5.0 out of 5 stars

Cayden was excellent. He took great care of our pets and house while we were gone for the week, staying in communication with me the whole time. Our dog is quite afraid of thunderstorms and Cayden made us feel at ease that Cilantro was in good hands when we couldn’t be there during a week of summer rain. Will absolutely book again, thanks so much Cayden!!

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Jul H.
House Sitting
5.0 out of 5 stars

Danica took great care of both my dog, Stella, and our house during her home stay. She communicated regularly and sent photo updates. She was home regularly to let Stella out, play with her, and feed her. The house was spotless upon our return and Stella seemed happy as can be. I definitely recommend booking with Danica and hope to have her come stay with Stella again!

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Bianca S.
House Sitting
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Find pet care near you

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 Chestnut Grove 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 Chestnut Grove 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 Chestnut Grove 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 Chestnut Grove 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 302 house sitters in Chestnut Grove. 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, 92% of Chestnut Grove house sitters respond in under an hour.

House sitters in Chestnut Grove have an average of 20 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 Chestnut Grove.

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. Chestnut Grove 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.