Dog Boarding Winterham

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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: Matthew B.
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Matthew B.
Star Sitter
from
$32
per night
5.0 out of 5 stars
• 30 reviews
12 repeat clients
15 years of experience
Midlothian, VA, 23112

“Matthew & Lucky are the best! They have always taken great care of my sweet Bailey. She has stayed with them several times & has always had the best time playing with her friends 🐾 Daily photos & updates are provided as well. I definitely recommend booking with them & look forward to bringing Bailey back soon!”

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Shaneka K.
Sitter Profile Image: PC & Will H.
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PC & Will H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 42 reviews
17 repeat clients
20 years of experience
Moseley, VA, 23120

“PC and Will took excellent care of our dog Bunny. They sent us several videos and pictures throughout the week. We could not be more pleased with the care and attention they gave to Bunny. I highly recommend PC and Will!”

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Vicki H.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
• 336 reviews
93 repeat clients
30 years of experience
North Chesterfield, VA, 23236

“We love Damacia, and so does our Onyx. She has taken care of him since he was a young puppy and has even provided insight/suggestions in things to add into his daily routine. He has grown a lot and LOVES her so much.”

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Cierra B.
Sitter Profile Image: Joy D.
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Joy D.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 87 reviews
40 repeat clients
7 years of experience
Midlothian, VA, 23112

“Joy was absolutely incredible! Sometimes my puppy can be a little nervous, but he played so well with the dogs at her house. She communicated with me well, and I could tell Kolbie loved being there. Very happy dog mommy here!”

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Angel D.
Sitter Profile Image: Josephine J.
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Josephine J.
from
$40
per night
5.0 out of 5 stars
• 11 reviews
2 repeat clients
20 years of experience
Moseley, VA, 23120

“Outstanding in every way!! Bailey (our pup) loves going there & always comes home happy & well cared for! This is our 2nd time using Josephine to dog sit & we couldn't be more happy with the experience both times!!”

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Susan D.
Sitter Profile Image: Cassandre S.
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Cassandre S.
from
$40
per night
5.0 out of 5 stars
• 328 reviews
73 repeat clients
30 years of experience
Midlothian, VA, 23114

“Cassandre is amazing! Our pup always looks so happy in the pics and videos she sends. I couldn’t ask for a better sitter for Evie and always hope she is available for the times we are away!”

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Brett M.
Sitter Profile Image: Deborah S.
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Deborah S.
from
$25
per night
5.0 out of 5 stars
• 3 reviews
3 repeat clients
30 years of experience
Amelia Court House, VA, 23002

About: I have taken care of all kinds of pets, from horses to kittens. I have recently completed a Red Cross course in dog and cat first aid. Providing quality care to meet your pets’ specific needs is my goal. My flexible routine allows me to provide pet care through out the week. Whether it’s a quick check in or a long walk, I’ll be there. Your home deserves to be respected. I can be trusted to treat your home as gently as I treat your pet. Your home will be left the same as it was when I arrived.

Sitter Profile Image: Jayla & Yolanda T.
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Jayla & Yolanda T.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 19 reviews
4 repeat clients
20 years of experience
Midlothian, VA, 23112

“Jayla took great care of our Draco! We went on vacation for Christmas and were so lucky to have found Jayla. Jayla provided several updates on Draco per day and really made him feel at home during the holiday. Draco enjoyed his stay so much he didn’t want to come home when it was time for pick-up! We will definitely be using Jayla’s services again!”

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Khala R.
Sitter Profile Image: Darling C.
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Darling C.
from
$36
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
8 years of experience
Richmond, VA, 23235

“Darling was amazing and Charlie had a wonderful time at her house. Very communicative and made us feel very comfortable. Will be booking her again!”

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Louis B.
Sitter Profile Image: Dylan H.
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Dylan H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 581 reviews
214 repeat clients
20 years of experience
Chester, VA, 23831

“I am so happy with Dylan! He took excellent care of my dog, Max, sending regular updates and photos throughout my trip(s), which really put my mind at ease. Max got ill while in Dylan’s care and he went up and beyond and brought Max to his primary Vet to ensure he was cared for. Max always seemed relaxed and happy when he returned home. As long as Dylan is available, I will definitely be booking with him!”

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Jimmy D.
Sitter Profile Image: Thurman Elaine & Steven B.
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Thurman Elaine & Steven B.
from
$45
per night
5.0 out of 5 stars
• 36 reviews
11 repeat clients
25 years of experience
Dinwiddie, VA, 23841

“Ms.Elaine was very helpful to me when I needed someone to watch my dog she was very caring and kept me updated on how Chaval was doing I would recommend her to any that needed services.”

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Janice M.
Sitter Profile Image: Natasha S.
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Natasha S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 18 reviews
2 repeat clients
15 years of experience
Rockville, VA, 23146

“Natasha is awesome! Thank you so much for taking such wonderful care of Charlie. He came home so relaxed and happy. She took Charlie for walking also. She has such a kind, gentle way with dogs, and her communication was fantastic—frequent photos, updates and super prompt responses the whole time. We will absolutely look to her for future pet care and will gladly recommend her to everyone we know!”

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Janardana P.
Sitter Profile Image: Elizabeth M.
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Elizabeth M.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 244 reviews
84 repeat clients
15 years of experience
Henrico, VA, 23238

“Sally was well cared for and had a great stay last weekend! My high energy lab had lots of play time and Elizabeth sent me many photos and updates. Highly recommend Elizabeth, thank you!!”

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Aimee H.
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
• 88 reviews
32 repeat clients
17 years of experience
Chesterfield, VA, 23838

“Dogs had a great time! We were updated daily with photos and videos and felt comfortable knowing our dogs were well taken care of, will definitely be booking again :)”

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Juliana A.
Sitter Profile Image: Verlee B.
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Verlee B.
from
$60
per night
5.0 out of 5 stars
• 14 reviews
10 repeat clients
15 years of experience
Amelia Courthouse, VA, 23002

“Verlee was amazing with my little girl!! Great communication, sent pictures, easy drop off and pick up. I will definitely use Verlee again!!”

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Kim D.
Sitter Profile Image: Julie W.
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Julie W.
Star Sitter
from
$48
per night
5.0 out of 5 stars
• 82 reviews
15 repeat clients
30 years of experience
Carillon, Richmond, VA, 23221

“During July 4th, we planned on going out of town for the weekend. We were impressed with Julie's rover profile and decided to contact her. We were able to meet up with her twice, once so that she could see our dog, and the second time so that Mozzie could check out her place. This was the first time since adopting him over a year ago that were had ever boarded him somewhere, so we were understandably nervous about it, but Julie proved to be a great sitter. She sent us status updates and pictures while we were away, so that we could know what Mozzie was up to. When we came to pick him up, she also helped us with tips and ideas on how to help Mozzie socialize with other dogs. We could definitely tell that Mozzie was in good hands. Definitely recommended!”

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Kathy S.
Sitter Profile Image: Jennifer A.
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Jennifer A.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 102 reviews
40 repeat clients
20 years of experience
Richmond, VA, 23233

“This was our first time using Rover. Jennifer was great and easy to work with. She sent updates and pictures which really helped put us at ease.”

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Catherine M.
Sitter Profile Image: Caitlyn & Samuel E.
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Caitlyn & Samuel E.
Star Sitter
from
$27
per night
5.0 out of 5 stars
• 44 reviews
10 repeat clients
20 years of experience
Midlothian, VA, 23114

“Caitlyn and Sam were so great with my dog and truly treated him like family! My dog can be a handful so having a sitter who enjoys him as much as I do is very important. I will definitely use them again!”

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Kate S.
Sitter Profile Image: Jamie H.
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Jamie H.
from
$35
per night
20 years of experience
Westover Hills, Richmond, VA, 23225

About: It's pretty simple - I love dogs and I work from home. Having recently said goodbye to my own best boy, Gary (a squishy English bulldog mix), I can guarantee that I'll get as much happiness out of seeing your dog as your dog will hopefully get from seeing me! I understand how important it is to know your pet is comfortable in your absence. I will treat yours as my own and send you as many updates as you'd like! Some key skills that may come in handy: - Walking dogs with leash reactivity - Experience with senior pets and those with medical needs - Administering medications, injections, paw wraps, etc. I'm currently working from home full-time, so I'll have plenty of time to play and love on your pups! I'm available for boarding all day, every day and would be happy to have a four-legged coworker around :) I have a fenced yard to keep your fur baby safe while exploring and getting lots of sniffs! We also keep a clean and tidy home to ensure your pet is always safe. Of course, there may be times when I need to step out (I'm human after all!), but will be happy to abide by any requests you have. Things like bowls, leashes, light up collars, pet gates, and a crate can be made available.

Sitter Profile Image: Deven & Tyreek C.
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Deven & Tyreek C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 32 reviews
17 repeat clients
15 years of experience
North Chestefield, VA, 23237

“We had an amazing experience boarding our dog with Deven and Tyreek from start to finish! They treated Riot just like their own; he was happy, comfortable and loved! Their communication was excellent, especially the frequent updates they sent with pictures and videos to show us how much fun Riot was having. We (Riot included) are grateful for the care they provided and would absolutely book them again in the future!!”

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

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    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 - Winterham

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FAQs for Dog Boarding - Winterham

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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 Winterham 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 Winterham.

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.

You and your Winterham 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.

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