Dog Boarding Windsor Hills

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Windsor Hills, 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: Amanda B.
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Amanda B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 41 reviews
16 repeat clients
20 years of experience
Chester, VA, 23831

“Frank had such a great time with Amanda! She was incredibly communicative throughout his stay and kept us updated with lots of photos and videos, which we really appreciated. It was so nice being able to see how happy and comfortable he was while we were away. Frank clearly loved his time with her and, honestly, didn’t want to leave when it was time to come home! Amanda took great care of him, and we would absolutely recommend her to anyone looking for a caring and reliable sitter. We will definitely be booking with Amanda again!”

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Ashley A.
Sitter Profile Image: Siobhan H.
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Siobhan H.
from
$40
per night
5.0 out of 5 stars
• 42 reviews
21 repeat clients
20 years of experience
Chester, VA, 23831

“Siobhan did an excellent job taking care of my little fur child. I felt at ease for the entire week my fur baby was in her care. I would definitely use her services again ...100 percent. I was provided updates and pics while he was in her care. I recommend you give her a try, you won’t be disappointed.”

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Cassandra C.
Sitter Profile Image: Anika D.
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Anika D.
from
$38
per night
5.0 out of 5 stars
• 11 reviews
4 repeat clients
20 years of experience
South Chesterfield, VA, 23803

“Very professional and practical. The communication was punctual and timely. I was very pleased to see our dog having such a lovely time during my time away. Highly recommend Anita for your Rover needs.”

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Christopher S.
Sitter Profile Image: Allejah K.
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Allejah K.
Star Sitter
from
$34
per night
5.0 out of 5 stars
• 7 reviews
7 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: Lisa C.
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Lisa C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 71 reviews
22 repeat clients
40 years of experience
North chesterfield, VA, 23237

“Lisa was great with Charlie who can get a little anxious when I leave him in new surroundings. She kept me updated as he adjusted and made sure he was comfortable and happy the entire time!”

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Alli M.
Sitter Profile Image: Christine & Nick G.
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Christine & Nick G.
from
$40
per night
5.0 out of 5 stars
• 55 reviews
19 repeat clients
20 years of experience
south chesterfield, VA, 23803

“Love them! Their whole family was fantastic with our fur baby and made her feel right at home. We will definitely rebook with them, they are so sweet! We received so many photos during her stay and you could tell she was loved and cared for as their own.”

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Britney L.
Sitter Profile Image: Madelyn D.
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Madelyn D.
from
$30
per night
5.0 out of 5 stars
• 4 reviews
3 repeat clients
2 years of experience
Petersburg City, VA, 23805

“Madelyn took excellent care of my dog Link and provided me with consistent updates so that I knew he was in good hands. I chose her to board him while I was away for the holidays, and would highly recommend her to anyone looking to do the same. I could tell he was treated as if she was his own. Thank you!”

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Tyresse L.
Sitter Profile Image: Matthew B.
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Matthew B.
Star Sitter
from
$30
per night
5.0 out of 5 stars
• 25 reviews
7 repeat clients
15 years of experience
Midlothian, VA, 23112

“Matthew was a wonderful sitter! Brixx came back a happy, tired pup. Matthew communicated very and was flexible when I had something come up. Brixx recommended!”

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Jaclyn C.
Sitter Profile Image: Shay & Jake W.
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Shay & Jake W.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 37 reviews
8 repeat clients
30 years of experience
Henrico, VA, 23231

“Shay and Jake took fantastic care of our pug! We got regular photo and video updates, and she was happy and healthy when we came to pick her up! Shay even let me know a favorite toy Maple grew attached to while there, so I could have it waiting for her when she got home. Overall a absolutely top notch experience.”

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Brooke C.
Sitter Profile Image: Laura C.
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Laura C.
Star Sitter
from
$28
per night
5.0 out of 5 stars
• 18 reviews
7 repeat clients
16 years of experience
Richmond, VA, 23236

“Laura had my dog nova for a week.Great with keeping you updated on your pet.Nova had a blast will definitely use Laura again.My dog was sad to go home that’s how much fun she had”

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Wini P.
Sitter Profile Image: Michelle H.
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Michelle H.
from
$50
per night
5.0 out of 5 stars
• 13 reviews
7 repeat clients
25 years of experience
Chester, VA, 23831

“Michelle is loving, kind and very accommodating. Her house is spotless and your pet always comes first. She updates you just enough so you can enjoy your travels and not worry about anything. I don’t think our dog wanted to leave. She got so much attention and love. Michelle is wonderful!”

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Laura S.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
• 335 reviews
92 repeat clients
30 years of experience
North Chesterfield, VA, 23236

“Just the the test run, Damacia went above and beyond for the main event. Open communication, pics sent, and when we thought we would be caught in a flood and be a day late...no worries. Outside of family this is the only person I trust.”

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Melissa J.
Sitter Profile Image: Laura B.
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Laura B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 71 reviews
16 repeat clients
30 years of experience
Midlothian, VA, 23114

“Dale and Cyrus had a great time with Laura, DJ, and family! Communication was very easy and we were provided photo and text updates during the stay. We could tell they were having a great time and were treated extremely well. We picked up two very happy and healthy dogs! We will definitely book again for future trips.”

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Christian M.
Sitter Profile Image: Luisa & Robert T.
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Luisa & Robert T.
from
$28
per night
5.0 out of 5 stars
• 27 reviews
2 repeat clients
4 years of experience
Fort Lee, VA, 23801

“My baby had a GREAT stay, thank you so much! They also were more than happy to keep him an extra night LAST MINUTE! Super appreciative of that! Definitely booking again!?”

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Nicole F.
Sitter Profile Image: Andrada T.
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Andrada T.
from
$45
per night
5.0 out of 5 stars
• 17 reviews
8 repeat clients
10 years of experience
North chesterfield, VA, 23237

“Andrada was wonderful! She sent us daily pictures, videos and updates. She responded quickly and worked with our schedule. I will 100% recommend her. We will most definitely be returning in the near future. Kizzez will miss Molly and Zara ?!”

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Sorina M.
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: Aaren & Jordon D.
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Aaren & Jordon D.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 30 reviews
7 repeat clients
6 years of experience
Swansboro, Richmond, VA, 23224

“Aaren & Jordon are truly wonderful puppy sitters! Throughout my pup’s stay with them, I received multiple updates during the day of the fun activities they were getting into. We were put at ease and loved to see our girl so happy while we were apart! We are thankful for them for welcoming our pup into their home with open arms.”

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Noralee S.
Sitter Profile Image: Amber C.
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Amber C.
Star Sitter
from
$44
per night
4.9 out of 5 stars
• 50 reviews
15 repeat clients
8 years of experience
Midlothian, VA, 23112

“Amber did a great job taking care of our 18 month old dog,Blu. She sent in frequent updates about him. She was kind enough to accommodate our last minute requests.Definitely recommend her!”

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Shivani P.
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

“Elaine and Steven are very kind! Winnie enjoyed her time with them. Elaine sent us pictures and a video. It was so nice to know she was so well taken care of.”

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Nancy W.
Sitter Profile Image: Jonathan P.
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Jonathan P.
from
$40
per night
5.0 out of 5 stars
• 118 reviews
36 repeat clients
10 years of experience
Henrico, VA, 23231

“Jonathan is great!! He was able to take my baby with one day notice for an entire weekend. He has great dogs too that are great playmates for my furbaby. The house is clean and in a very convenient location for me. Will definitely use Jonathan again. I have also recommended him to my friends!”

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Sherina G.
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Dog parents share their Rover experiences - Windsor Hills

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5.0 out of 5 stars

I’ve booked with Leidy a couple of times now and she is great! She’s very communicative and sends pictures everyday! My dog comes home happy and is excited at every drop off.

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Jade E.
Boarding
5.0 out of 5 stars

Allejah really is a five star sitter! Communication and knowledge of doggie behaviors, attention to detail, flexibility, and LOVE are all top tier. This was my first boarding experience and I have a senior dog so I was on pins and needles going in- my anxiety was eliminated after meeting Allejah and receiving my first round of doggie mail. My old pup was just as comfortable and cantankerous with her as he is with us:-). I appreciated that she made my Velcro dog feel comfortable enough to relax, rest, and cuddle. As an anxious pet parent- I was comfortable enough to enjoy my travels. I would 100% recommend her and I’d love to have her puppy sit again when the need arises.

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Sunni J.
Boarding
5.0 out of 5 stars

Rikki is amazing! this is our second time booking with her and this time was a longer stay than the first time and our boy had a great time. rikki really cares for your babies like she cares for her own.

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Gracie T.
Boarding
5.0 out of 5 stars

Anika took such great care of my dog, was in constant communication with me on how he was doing with pictures, and was super flexible and understanding about pick up and drop off times. Absolutely will be using her again!

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Maddison G.
Boarding
5.0 out of 5 stars

Siobhan was great! She kept me posted about Shade and sent pictures. I liked she had other dogs for Shade to interact with. A plus is Siobhan’s location is very convenient to where I live. This is the third time I requested her services, however was only fortunate to book twice. Very pleased and would recommend!

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Patricia M.
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

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

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
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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

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

  • 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

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog boarding - Windsor Hills

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FAQs for Dog Boarding - Windsor Hills

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 Windsor Hills home-away-from-home, 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 Windsor Hills.

<b>Tip:</b> 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 Windsor Hills 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 , 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 .

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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