Dog Boarding in Chester

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Top rated Chester dog boarders

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: Dylan & Alex B.
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Dylan & Alex B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
534 reviews
199 repeat clients
20 years of experience
Chester, VA, 23831

Dylan and Alex were amazing! They took excellent care of our pup while we’re were out of town for a week. We got daily updates and pictures and any question we had was answered within minutes. Will definitely book with this sitter again and highly recommend.

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Jarrod P.
Sitter Profile Image: Charlotte B.
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Charlotte B.
from
$25
per night
4.9 out of 5 stars
194 reviews
113 repeat clients
25 years of experience
Chester, VA, 23831

Charlotte is so so sweet, very communicative, organized, kind, friendly, and overall, the perfect person! She had some doggy friends for my dog to play with, which was a huge plus. I was at ease while traveling out of state. Do not hesitate to book her!!

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Miatta H.
Sitter Profile Image: Amy & Grant P.
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Amy & Grant P.
Star Sitter
from
$34
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
3 years of experience
Chester, VA, 23831

Amy and Grant are wonderful. They were welcoming and flexible with Ollie’s needs, especially as their own pup was recovering from an injury. They have a nice big yard for play, communicated regularly, and it was obvious they cared to make Ollie’s stay comfortable for him and their family.

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Kimberly W.
Sitter Profile Image: Kendra B.
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Kendra B.
Star Sitter
from
$25
per night
5.0 out of 5 stars
38 reviews
7 repeat clients
25 years of experience
North Chesterfield, VA, 23237

Kendra is the best! Yasha loves her and Gizmo and lights up whenever I tell her she is going to see them. She is personable and treats my baby like her own!

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Tawana B.
Sitter Profile Image: Amanda & Adam B.
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Amanda & Adam B.
Star Sitter
from
$33
per night
5.0 out of 5 stars
76 reviews
27 repeat clients
17 years of experience
Chesterfield, VA, 23838

Marshmallow had an amazing time! He didn’t want to leave when we came to get him. He was very tired when we got home and was the quietness he’s been, which is saying something for a 4 month old puppy!! Will definitely be coming back soon.

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Michael W.
Sitter Profile Image: Shay & Jake W.
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Shay & Jake W.
from
$35
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
30 years of experience
Henrico, VA, 23231

Shay and Jake always do a wonderful job with our dog Maple, but this time they truly went above and beyond when she had some tummy trouble. Leaving Maple with them feels like leaving her with family.

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Brooke C.
Sitter Profile Image: Jay B.
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Jay B.
Star Sitter
from
$39
per night
5.0 out of 5 stars
310 reviews
98 repeat clients
30 years of experience
Henrico, VA, 23231

This was the first time we have ever used a sitter for Dough. I was hesitant at first but Jay definitely helped cap my insecurities. The communication was top tier! The random pictures eased my mind. When we picked him up he didn't want to leave lol. He tried to go back to the door. Needless to say, we will be back! Thanks so much for hosting Dough! We appreciate you!

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Aria H.
Sitter Profile Image: Abby M.
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Abby M.
Star Sitter
from
$38
per night
5.0 out of 5 stars
282 reviews
97 repeat clients
14 years of experience
Chester, VA, 23831

Abby was accommodating for a meet and greet, which I greatly appreciated; Oliver gets scared when I drop her off to stay with a stranger. Abby provided daily pictures and updates on how Oliver was doing and she came back very happy. I would use Abby again to pet sit.

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Emily B.
Sitter Profile Image: Leidy C.
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Leidy C.
from
$35
per night
5.0 out of 5 stars
1 review
1 repeat client
5 years of experience
Colonial Heights, VA, 23834

About: I’ve always had a deep love for animals and truly enjoy caring for them as if they were my own. I’m a responsible, patient, and attentive person who understands how important it is for pet parents to feel at ease while they’re away. I have experience caring for dogs of different sizes and personalities, including feeding, walks, playtime, and making sure they feel safe and loved. I pay close attention to their behavior and needs, and I’m comfortable following specific routines or instructions. I will treat your pet with love, respect, and care—just like family. 🐾💛 I’m also very communicative and will send regular updates, photos, and videos so you can feel connected and worry-free. I work from home running my small business, which allows me to be present and attentive throughout the day. The only times I step out are briefly to drop off and pick up my daughter from school. Because of this, your pet will rarely be left alone and will receive plenty of attention, playtime, and care. I’m available for boarding, daycare, and walks, with a flexible schedule to meet your pet’s needs. I provide a safe, calm, and loving environment where your pet will feel at home. I always prioritize their comfort and well-being, following any specific routines, feeding schedules, or instructions you provide. I supervise pets closely, keep a clean and secure space, and make sure they feel relaxed and cared for at all times. I’m also happy to send regular updates, photos, and videos so you can feel at ease while you’re away. Your pet will be treated with the same love and attention as my own. 🐾💛

Sitter Profile Image: Kourtney D.
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Kourtney D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
86 reviews
19 repeat clients
17 years of experience
North Chesterfield, VA, 23234

Kourtney is absolutely phenomenal! We were so worried because our usual Rover sitter was not available. Kourtney was very empathetic with our situation and made our CKCS fur baby feel comfortable. For those out there worried about their anxious pup with special needs, Kourtney is absolutely perfect and a brilliant sitter.

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Ben G.
Sitter Profile Image: Matt M.
Verified Enhanced Background Check
Matt M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
266 reviews
84 repeat clients
25 years of experience
Northern Barton Heights, Richmond, VA, 23222

Matt is phenomenal and we couldn’t be happier with our experience! From the moment we dropped our dog off, it was clear how thoughtful, attentive, and genuinely caring he is. His home is welcoming and clearly set up with dogs in mind, and we felt completely at ease leaving our dog there overnight. We received great updates, and it was obvious our dog was comfortable, well cared for, and having a great time. When we picked him up, he was happy, relaxed, and clearly had been treated like one of the family. It’s such a relief to have a sitter we trust completely - this is exactly what you hope to find. We will absolutely be booking again and can’t recommend Matt highly enough!

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Lucile R.
Sitter Profile Image: Cindy T.
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Cindy T.
Star Sitter
from
$42
per night
5.0 out of 5 stars
300 reviews
82 repeat clients
20 years of experience
north chesterfield, VA, 23235

Mrs Cindy is what me and Rocky needed. She took excellent care of my baby. This was Rocky 1st time at a siter. She took pictures and kept me updated. Loved the experience and would definitely take Rocky back if needed

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Krb516 B.
Sitter Profile Image: Royal & Rhonda P.
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Royal & Rhonda P.
from
$40
per night
5.0 out of 5 stars
157 reviews
50 repeat clients
5 years of experience
Chesterfield, VA, 23237

My dog stay went well. I was worried about leaving her with strangers and how she would adapt, but Royal and Rhonda did a great job with her. They also sent us a lot of updates with pictures which made us feel at ease. I would definitely recommend them. Thanks

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Mark P.
Sitter Profile Image: Ari & James S.
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Ari & James S.
Star Sitter
from
$30
per night
5.0 out of 5 stars
65 reviews
16 repeat clients
15 years of experience
Chesterfield, VA, 23838

We left our doggie with Ari while traveling for two weeks and we couldn't have asked for anyone better to look after him. Our special boy is a senior Schnoodle that we rescued last year from a breeder situation gone really bad. Ari and her family welcomed him with open arms and treated him like he was one of the family. She sent daily updates and we thought our boy may not want to come home after seeing how much fun he was having in the photos. Also, he made a new best friend with the family dog Apollo. I would recommend Ari to anyone that is looking for a home-away-from home for their fur babies.

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Gloria H.
Sitter Profile Image: Andrea B.
Verified Enhanced Background Check
Andrea B.
Star Sitter
from
$38
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
4 years of experience
Chester, VA, 23831

Could not speak more highly of her! Took excellent care of my pets and even took one to the emergency vet when she broke a tooth (known rock chewer). Would not trust anyone else

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Alexandria M.
Sitter Profile Image: Allejah K.
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Allejah K.
Star Sitter
from
$34
per night
5.0 out of 5 stars
6 reviews
5 repeat clients
14 years of experience
SOUTH CHESTERFIELD, VA, 23834

Cameron absolutely loved his stay at Allejah’s home. She stayed in close contact with us and gave Cameron the best possible care. We are so thankful to have found her!

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Taylorann B.
Sitter Profile Image: Radka & James A.
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Radka & James A.
Star Sitter
from
$35
per night
5.0 out of 5 stars
215 reviews
68 repeat clients
18 years of experience
Moseley, VA, 23120

Amazing people, awesome care for our dog Artanis. Pictures everyday. Awesome communication and nothing but love! They were so great we know Artanis wants to go back!!

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Phillip G.
Sitter Profile Image: DAMACIA J.
Verified Enhanced Background Check
DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
315 reviews
84 repeat clients
30 years of experience
North Chesterfield, VA, 23236

Highly recommend. Damacia took care of Teddy very well.. Teddy attached to her as a family member. She updated every day with his picture. Thanks Damacia 🥰

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Alwin R.
Sitter Profile Image: Abreya K.
Verified Background Check
Abreya K.
from
$55
per night
4.8 out of 5 stars
48 reviews
18 repeat clients
23 years of experience
Chester, VA, 23831

I needed someone to care for my fur baby as I would and Abreya did an outstanding job boarding my dog. She kept me informed and sent photos everyday. I plan on using her again in the future.

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Patricia N.
Sitter Profile Image: Hilary R.
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Hilary R.
Star Sitter
from
$38
per night
5.0 out of 5 stars
217 reviews
73 repeat clients
20 years of experience
Reedy Creek, RICHMOND, VA, 23225

I am beyond thankful for the care Hillary provided my dog with this weekend. I was feeling nervious about leaving my baby somewhere new but he had a great time and I received pictures throughout his stay. I will absolutely book Hillary again and I know rocky will enjoy more sunbathing and yard chases next time! Thank you, Hillary.

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Katy R.
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Over 1,649
pet parents in Chester have booked dog boarding

Chester dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Charlotte did an amazing job keeping us in the loop on how our doggies were doing while we were away.

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Kevin H.
Boarding
5.0 out of 5 stars

Kendra was GREAT! I am skeptical about leaving my girl but knew Kendra could be trusted when my girl was eager to enter the house during our meet and greet session. During Demie's stay, Kendra sent morning and afternoon check-ins with photos daily. She took GREAT care of my baby! I will be booking my her next stay immediately.

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Chantel R.
Boarding
5.0 out of 5 stars

Amanda was amazing! She took great care of my dog and cat ensuring I got daily pictures and updates for how they were doing. She followed all my instructions for my dog who has arthritis. I will definitely use her again!

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Emily B.
Boarding
5.0 out of 5 stars

I always feel secure with leaving my Boston terrier with Stephanie. It’s also nice the she has a small dog that can play with my dog. I received daily pictures and videos of my dog. I have used Stephanie a few times and I also satisfied with service.

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Mashia O.
Boarding
5.0 out of 5 stars

Amy and Grant are wonderful. They were welcoming and flexible with Ollie’s needs, especially as their own pup was recovering from an injury. They have a nice big yard for play, communicated regularly, and it was obvious they cared to make Ollie’s stay comfortable for him and their family.

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Kimberly W.
Boarding
5.0 out of 5 stars

This was my pup’s second stay with Michelle and it went just as smoothly as the first time. I always get nervous leaving my dog for any period of time, but especially for long trips. Michelle is thoughtful and welcoming and does an amazing job taking care of my dog.

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Hannah N.
Boarding
5.0 out of 5 stars

Abby is wonderful and took great care of my sweet, but nervous dog. I would recommend her for your pet needs. She is also very communicative.

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krista h.
Boarding
5.0 out of 5 stars

Everything went very smoothly with Abreya, from the communication, the meet and greet until the end of my babies stay. Had a very pleasant experience. I was happy and my babies were happy. Will book with her again.

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Maria R.
Boarding
5.0 out of 5 stars

Jeanette, took very good care of my two dogs. I will definitely use her again. My girls seemed very happy and at home when I picked them up.

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Patrick C.
Boarding
5.0 out of 5 stars

Our dogs love going to his house. They get really excited everytime we drive near it. Denny is very responsive and great with my dogs. We have used his services many times. You couldn't ask for a better sitter/handler.

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Z A.
Boarding
5.0 out of 5 stars

Beverly was amazing. I am thankful for the care she gave our dog Ziggy and for the daily updates with videos. She is very considerate and lovely to work with, I would recommend her to anyone that is thinking of boarding their dog.

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Darling C.
Boarding
5.0 out of 5 stars

Pups were happy little campers with Rangeen and Mike! We were able to relax knowing they were well taken care of. Will for sure be booking again! Thanks!

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Abbie M.
Boarding
5.0 out of 5 stars

They did a wonderful job taking care of our very spoiled great dane, Suvi. Will definitely book again!

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Jennifer F.
Boarding
5.0 out of 5 stars

Leigh and her family are so kind and wonderful to work with. I was glad to leave Duke in her care again!

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Adam S.
Boarding
5.0 out of 5 stars

Lisa loved on our pup over Christmas, sent lots of pics and took good care of him. She knows her dogs and seems to enjoy their company.

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Ashley R.
Boarding
5.0 out of 5 stars

Great doggie caregiver service! She loved on my dog, just like I would! She sent photos too! Thank you!

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Wanda D.
Boarding
5.0 out of 5 stars

We recently hired Claire to care for our dog AJ, a 4 year old retriever , while we were away for an entire month. Overall, the experience was excellent, and we felt confident that our boy was in capable hands. From the start, communication was smooth and timely. Claire made sure to ask detailed questions about AJ’s routine, diet, preferences, and quirks, which gave us peace of mind. During the stay, she provided regular updates and photos, showing walks, playtime, and quiet moments — a thoughtful touch we really appreciated. Our dog seemed relaxed and happy upon our return. It was clear Claire took her responsibility seriously and genuinely cared for our pet’s well-being. She was by far our best boarding experience. We would absolutely recommend Claire to other pet owners looking for reliable and attentive care. We’re already planning to rebook for our next trip!

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Jamie W.
Boarding
5.0 out of 5 stars

Annabella was quick to communicate and helped us tremendously with our pup when a last minute issue came up on our end. She really saved the day and treated Otis like he was her own. It was wonderful to receive so many photos and details of his day!

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Corinne C.
Boarding
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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding in Chester is $45

Why Choose Rover?

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

  • Reservation protection

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

  • World-class support

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

Sitters in Chester average 12
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Chester is $45 per night, including service fees. Boarding your dog for one week typically costs $315. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chester dog boarding rates can be found as low as $26 to as high as $49 per night.

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

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

As of Jun 2026, 761 sitters provided dog boarding in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 93% of Chester dog boarding sitters respond in under an hour.

Sitters who provide dog boarding in Chester have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 12 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Chester.

Rover makes it easy to find Chester dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

There are 761 dog boarding sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 97% of sitters offer daily exercise, 96% offer medication administration, and 92% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.