Dog Boarding Chestnut Grove

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Chestnut Grove, Find top rated dog boarding

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: Bertie & Lissette A.
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Bertie & Lissette A.
from
$50
per night
5.0 out of 5 stars
• 154 reviews
65 repeat clients
20 years of experience
Charlottesville, VA, 22911

“Bertie, Liss and family are absolutely wonderful! It was the first time leaving my puppy overnight and they were kind, responsive and helpful. They took great care of my pup, treated her like their own, and sent lots of updates. I can’t recommend them enough and will absolutely book with them again!”

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Teresa W.
Sitter Profile Image: Paula C.
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Paula C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 200 reviews
55 repeat clients
25 years of experience
Charlottesville, VA, 22911

“Paula took great care of my anxious dog, Peaches, during a long overnight stay while I was recovering from surgery. She was patient, calm, and attentive, and Peaches absolutely loved her. I felt confident knowing Peaches was safe and well cared for the entire time. I would happily book with Paula again.”

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Jenna J.
Sitter Profile Image: Amanda S.
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Amanda S.
from
$40
per night
4.9 out of 5 stars
• 48 reviews
8 repeat clients
5 years of experience
Ruckersville, VA, 22968

“Amanda was great! She was communicative and sent us adorable photos of our boy throughout his stay. Our boy was treated like family and became best friends with her dog. I truly appreciate how much love he received while we were away!”

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Kiara G.
Sitter Profile Image: Hope B.
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Hope B.
from
$40
per night
5.0 out of 5 stars
• 89 reviews
37 repeat clients
10 years of experience
Charlottesville, VA, 22911

“Hope is amazing! She was very communicative and provided us with the best pictures and updates of Biscuit. We appreciate her time and flexibility with our schedules and look forward to seeing her and Loretta again soon!”

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Laurentia T.
Sitter Profile Image: Heather & Nigel S.
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Heather & Nigel S.
from
$60
per night
5.0 out of 5 stars
• 180 reviews
80 repeat clients
15 years of experience
Charlottesville, VA, 22911

“I fully recommend Heather. Our dog had a great time with her and her family. She sent us updates every day, and we could see how well our dog was doing. Their location is also great - a paradise for any dog who likes to run around and play.”

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Henriette S.
Sitter Profile Image: Kathryn H.
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Kathryn H.
Star Sitter
from
$32
per night
5.0 out of 5 stars
• 38 reviews
21 repeat clients
20 years of experience
Stuarts Draft, VA, 24477

“Kathryn was great with our 7 month old cavalier mix. You can tell she loves what she does & I immediately felt safe leaving her. I highly recommend her & will be using her going forward for any overnight stays in the future!”

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Cynthia D.
Sitter Profile Image: Brianne C.
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Brianne C.
from
$45
per night
5.0 out of 5 stars
• 30 reviews
16 repeat clients
10 years of experience
Charlottesville, VA, 22901

“Brianne was great! Worked very well with my drop off and pickup times. The dogs had a big yard the even my one escape artist couldn’t find a hole in. I’ll definitely be using her for any future trips!”

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Shane S.
Sitter Profile Image: Ashley B.
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Ashley B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
10 years of experience
Charlottesville, VA, 22901

“Ashley watched my Lexie, 5 and a half year old black lab, for 6 days. She provided me daily updates and photos of Lexi's activities to keep me informed that she was doing well. I highly recommend Ashley as a resource to care for your dog as well.”

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Scott S.
Sitter Profile Image: Julie N.
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Julie N.
Star Sitter
from
$58
per night
5.0 out of 5 stars
• 45 reviews
15 repeat clients
35 years of experience
Charlottesville, VA, 22902

“Julie and her family took wonderful care of Willa! She got to go on plenty of walks and enjoyed lots of snuggles. Julie sent pictures and was easy to communicate with. Willa came home happy and we will definitely book with her again!”

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Lisa S.
Sitter Profile Image: Roy T.
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Roy T.
from
$45
per night
20 years of experience
Fifeville, Charlottesville, VA, 22903

About: Having had dogs and cats my entire life, I am well prepared to take care of your furry friend. Having had a dog with severe allergies, I am also prepared to take care of any pets with chronic health conditions that require more attention As a medical student in a hybrid learning environment, I have a flexible schedule that provides me the time to tend to your pets as needed. Caring for my own dog, your pet can fit seamlessly into our schedule for walks, bathroom breaks, and play time. I take all pets on several walks a day, providing them ample time to exercise and play outside. In caring for my clients home, I will make sure their pet abides by all house rules and maintain a clean living space for their home.

Sitter Profile Image: Amy H.
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Amy H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 134 reviews
32 repeat clients
21 years of experience
Faber, VA, 22938

“Amy was amazing and I could not recommend her enough!! She took the best care ever of our 1 year old pup and he came home so happy and tired from all the love and play Amy provided. She has a perfect house and yard for the dogs, sends so many updates and pictures, and is very communicative and kind. She clearly loves dogs and is a trustworthy person you can rely on to take excellent care of your pups! We will certainly be using her again in the future!”

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Lesley C.
Sitter Profile Image: Mary Alice C.
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Mary Alice C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 61 reviews
11 repeat clients
6 years of experience
Gordonsville, VA, 22942

“Mary Alice took amazing care of my cat, Tilly! She was super communicative -- sending multiple photos and videos of Tilly daily. She went above and beyond on play time. I'd recommend Mary Alice wholeheartedly!”

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Julia R.
Sitter Profile Image: Kirstin S.
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Kirstin S.
from
$63
per night
5.0 out of 5 stars
• 15 reviews
1 repeat client
25 years of experience
Charlottesville, VA, 22911

“Kirstin is the best! Can’t say enough good things! Our new rescue puppy Sky is a little timid and needs lots of reassurance. Kirstin provided such a calm & cozy place for her last week & sent lots of updates and pics. I had a great vacation knowing Sky was safe, having fun & even napping with Kirstin’s kitty!”

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Peggy M.
Sitter Profile Image: Reagan A.
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Reagan A.
from
$60
per night
5.0 out of 5 stars
• 2 reviews
6 years of experience
Main-Starr Hill, Charlottesville, VA, 22903

“Reagan was available on short notice and great to work with. Biscuit had a good time.”

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Eddie S.
Sitter Profile Image: Tea R.
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Tea R.
from
$32
per night
5.0 out of 5 stars
• 17 reviews
6 repeat clients
10 years of experience
Harrisonburg, VA, 22801

“Tea took great care of my very spoiled chihuahua. She's responsive and sent updates and photos throughout the booking. We will definitely rebook with her again!”

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Kathy R.
Sitter Profile Image: Alexa H.
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Alexa H.
from
$50
per night
5.0 out of 5 stars
• 19 reviews
8 repeat clients
8 years of experience
Orange, VA, 22960

“Alexa is a professional with a lot of knowledge about dogs, training, and how to make sure they are comfortable and sage while she watches them.”

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Alesia Q.
Sitter Profile Image: Tamara T.
Verified Enhanced Background Check
Tamara T.
from
$50
per night
5.0 out of 5 stars
• 38 reviews
15 repeat clients
22 years of experience
Palmyra, VA, 22963

“Tamara was AWESOME! Gizmo had a great stay with her and was extremely relaxed when I picked him up. She was able to watch him at short notice as well and even washed his food and water bowls for me!”

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Shaelin N.
Sitter Profile Image: Alyssa C.
Verified Background Check
Alyssa C.
from
$50
per night
5.0 out of 5 stars
• 44 reviews
12 repeat clients
30 years of experience
Harrisonburg, VA, 22801

“Alyssa and Sean are fantastic! They took such good care of my French Bulldog for a few days. They are extremely nice and you can tell they love taking good care of dogs! I was extremely comfortable with leaving Stewie with them! I will definitely use them again when I’m in the area! I highly recommend them!”

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Nikkole I.
Sitter Profile Image: Rachel F.
Verified Enhanced Background Check
Rachel F.
from
$25
per night
30 years of experience
Harrisonburg, VA, 22802

About: I've had a dog since I was about 7 years old. Between fostering both cats and dogs for the RHSPCA, and having goats, chickens, fish, parakeets, lizards and rabbits, pets aren't strangers around here. I love learning about each creature's individual personality and playing (or just snuggling!) in the way they like best. Our household operates on part-time work with one child homeschooling, making it easy to find time to care for your pet as well! It's a great part of the homeschool experience too ❤️ Although there are quite a few pets around, I also live in an old farmhouse with a zillion doors, making it easy to offer as much inside space as is appropriate for each critter. The fenced-in yard gives medium-sized dogs the opportunity to really RUN outside! And the availability of snugglers inside is perfect for any downtime :)

Sitter Profile Image: Margaret M.
Verified Enhanced Background Check
Margaret M.
from
$49
per night
5.0 out of 5 stars
• 11 reviews
35 years of experience
Lyndhurst, VA, 22952

“Margaret took great care of my anxious puppy! She was very communicative and sent plenty of updates! I could tell my dog was well loved and he came home happy and tired!”

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Emma K.
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The median cost per night for dog boarding in Chestnut Grove is $50

Dog parents share their Rover experiences - Chestnut Grove

1 / 1
5.0 out of 5 stars

Another excellent stay with Heather! It’s great to be able to leave your dog and know you don’t have to worry at all. Highly recommend!

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Maya C.
Boarding
5.0 out of 5 stars

She was amazing! I received pictures and updates while our dog was in her care. It made me feel really at ease seeing my dog so relaxed and enjoying her home/property. She was even able to accommodate extending her stay due to our travel being delayed. I HIGHLY recommend her and will definitely be using her services again! Thanks again Heather!

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Shayla P.
Boarding
5.0 out of 5 stars

My anxious dog warmed up to Heather in minutes and had the best time. Heather was excellent at communication and made us feel at ease leaving our dog in her care!! Would rebook, highly recommend, don’t hesitate.

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Maya C.
Boarding
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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?

  • Cashless payments

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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 dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

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Popular requests for dog boarding - Chestnut Grove

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Chestnut Grove average 11
repeat dog boarding clients

FAQs for Dog Boarding - Chestnut Grove

Frequently asked questions about Rover

As of November 2026, there are 232 sitters on Rover offering Dog Boarding across Chestnut Grove. Enter your ZIP code to see which available sitters are closest to your home.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

98% of sitters in Chestnut Grove can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chestnut Grove home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Chestnut Grove.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

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

  • 95% of sitters can help with special care needs
  • 96% 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.

You and your Chestnut Grove sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

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.

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in VA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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