Dog Boarding in Windsor, VA
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Windsor dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Rachel was great with communication for pre drop off, drop off, during stay and pickup. I was able to bring my pup over for a meet and greet with her and her dogs prior to the boarding. Has a great sized yard and friendly dogs. She sent video updates everyday which I loved. I would recommend and will be using her again in the future!”


“Megan was amazing I recently boarded my rescue Prince for the first time, and I couldn’t have asked for a better experience! Megan took such amazing care of Prince during his two-night stay. She went above and beyond—sending me some of the best photos and videos I’ve ever had of him, including clips of him playing and socializing with larger dogs (which was a first for him!). It meant so much to see him having that kind of fun and confidence. Megan also kept me updated with daily “doggy report cards” and personalized notes, which were such a thoughtful touch. When I picked him up, it was clear he had an incredible time—he was almost sad to leave! He even made a new best friend with her dog, Kava. I’m so grateful for the care and attention Megan gave, and I will absolutely be booking with her again. Truly a 5-star experience from start to finish!”


“My dogs LOVE going to Shelly's. She pays a lot of attention to them and they come home exhausted. Shelly is very accommodating and always reachable. Great experience.”

“For being a first time user and having my dog watched for the first time, I'm absolutely overly satisfied with the services we received! Communication was there, the process of meeting and greeting was smooth and easy, pictures were sent to me throughout my vacation(I LOVED), and just having the overall feeling that my dog was okay safe and well taken care of was a big PLUS for me being on vacation on the other side of the world! I could sit here and write a whole paragraph or more on all of the positive and my experience but, I will keep it short and say I just HIGHLY RECOMMEND! Thank you again for your services!”

“Robert and Taylor took amazing care of my young pitbull. They are very kind and friendly and really care about the well being of my baby. I will definitely be booking with them in the future.”

“Kimberly and her boys were amazing. We don’t vacation often because we don’t like leaving our beloved Ollie, Kimberly has changed that. She was very informative and flexible. She kept us updated and made sure Oliver was comfortable. Can’t wait to book again”

“Jessica and her family Treat our 3 boys like their own when they are there. Great communication and pictures of the boys are always a great touch too! Highly Recommend!”


“Well this was our Kobe first experience with Jackie or anybody since Covid came into our lives. Jackie made the process smooth and informative for us to know how our dog was doing we really appreciate that too so we thank you. She return our to us with good attitude and clean as he came there. So if anybody looking for an outstanding dog sitting Jackie is your best choice. We thank you again and will be using your service in the near future.”

“The best she did everything to accommodate my Trudy. She also went out her way to be available at the time I arrived from airport even though my flight was delayed. People don't understand how hard it can be planning a vacation or getting away when you have a pet, Vania was a lifesaver and Trudy enjoyed her stay as well.”


“I knew when I met Julie that this home was the right choice for our pup. There is nothing better than knowing your furry family member is in a good and loving environment while you're out of town. We could not have been happier and will use her and Kenneth again!”

“This was our second time with María and Matthew, and once again they were fantastic! I feel so at ease knowing my fur baby is in such loving and reliable hands. Highly recommend!”

“Lauryn was an incredible sitter! She accommodated all of my dogs’ needs and likes. She took care of my boys, Ace and Adonis, as if they were her own. I loved that she sent pictures and videos of them every day. It was such a bonus and put my mind at ease to see them having fun while I was away. I highly recommend her and we will be back! 🐾😊 Thank you Lauryn!”

“Gail was wonderful with Joy. I received pictures of Joy and a text on how Joy was doing. This was my 1st time using Gail and I was very happy with her care for my fur bady. I would recommend Gail service and I definitely will be coming back to her. Thank you so much!!”

“This is the 2nd time that Omaira and Isaac have taken care of my babies. Once again, they seemed very well taken care of. I felt guilty leaving them for so long, but they sent me many pics and videos of my dogs having fun to make me feel better. When I picked them up they looked very healthy. I can tell that they had a good experience at Omaira & Isaac's because when I took them out for a walk, they were more friendly with other people and dogs then they usually are. Even their grandma couldn't believe their good behavior! Thanks again guys!”

“Megan took care of my Wilson for two weeks and I’m so thankful I found her! Her and her family took such good care of my boy and I was so appreciative of her daily updates and photos. Thank you Megan and we will see you again!”

“Nathan was amazing with our golden retriever, Rosie, while my family and I were away on a trip. He was incredibly attentive and caring throughout her stay, making it extra special with toys, space to play, and daily activities to keep her entertained. His kids loved her and took great care of her as well, which was so heartwarming. Nathan kept me updated daily with photos and messages, giving us peace of mind. I highly recommend Nathan to anyone looking for someone who will truly treat their pets like family!”

About: I’ve owed 4 Labrador retrievers, and still currently have two, one is my duck dog and one’s my old retired boy. I love animals. We enjoy daily walks, and mental stimulation! They get plenty of outdoor time as well as one on one time! I’m currently working as an estimator from home so I have plenty of free time for animals and making sure they get the proper care they need while under my supervision! I have all necessities for animals. I have an out door dog run, I have indoor kennels, I have a designated area inside, I give mental stimulation toys and treats. I make sure the dogs are going outside atleast every two hours insuring the have there energy out and not missing any potty breaks man
“Tremendous, my puppy Bryson got plenty of exercise and attention. Honestly I think he was happier here than at home. Wesley sent pictures of Bryson playing with her puppies, so I didn’t miss him too much. Highly recommend, will employ again.”

Over 109 pet parents in Windsor have booked dog boarding
Windsor dog parents share their Rover experiences
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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. 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. Book & Pay
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The median cost per night for dog boarding in Windsor is $38
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 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 Windsor average 9 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, the median cost of dog boarding in Windsor is $38 per night, including service fees. Boarding your dog for one week typically costs $266. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Windsor dog boarding rates can be found as low as $31 to as high as $55 per night.
As of Jun 2026, 320 sitters provided dog boarding in Windsor. 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, 96% of Windsor dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Windsor have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 9 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 Windsor.
Rover makes it easy to find Windsor 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 320 dog boarding sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 97% of sitters offer daily exercise, 100% offer medication administration, and 97% 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.





