Dog Boarding in Windsor, VA
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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.
“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.”
“Rachel was great with Aspen. Her dogs and Aspen became fast friends very quickly. I received so many pictures it was delightful! When I ran out of time to bring Aspen to her, she was out not so far away and picked her up. Then was headed my way anyway, so returned her after I returned. Aspen will be very happy to go back as needed.”
“Cannot say enough good things. My pup was living his best life. Shelly set up a puppy area for him. But he also got to run with the chickens. She clipped his nails and gave him a bath! He loves her and it made my trip better knowing that he was in such good hands.”
“Sophie was at Angela and Bill’s for two weeks. First time I have left her for that long. They sent photos and I felt reassured that she was doing ok. And they survived my 86 lb Bernedoodle.! Would highly recommend.”
“Yvette was great with my 3 fur babies. She sent pictures and videos throughout the stay, which was very much appreciated. It was great knowing my babies were taken good care of while I was out of town. I will be booking with her whenever I need a sitter again.”
“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!”
“We felt safe with our dog there, and our dog seemed super contented being there. Kimberly was great with communication and photos—we’ve already booked her again!”
“Meghan was amazing! She sent a ton of pics and videos and really eased our mind with leaving our baby behind for the first time. Her and her family really went out of their way to make our furbaby feel at home. Meghan is kind and professional. You won’t find a better person to take care of your precious pup. She will absolutely be our go to in the future! Thanks again Meghan, so glad we found you!!”
About: What sets me apart is the presence and care I bring to every interaction. With 15+ years of hands-on experience across a wide range of animals—dogs, cats, reptiles, fish, chickens, rabbits, and guinea pigs—I’m not just pet sitting, I’m attuning. I notice the little things: a shift in behavior, a need for extra cuddles, or when it’s time to give space. My calm, loving energy helps animals feel safe and understood. I don’t rush through visits—I show up fully, giving your pet the same patience and warmth I give my own. As a homeschool mom with a flexible schedule and a peaceful home environment, pet sitting fits naturally into my life. I’m home most of the day, which means your pet gets consistent attention, companionship, and care—not just quick check-ins. Caring for animals is something I genuinely love, and it brings joy and balance to our rhythm at home. Whether it’s daily drop-ins or extended stays, I have the time, space, and heart to give your pet the presence they deserve. Whether your pet stays in my home or I care for them in yours, my approach is rooted in calm, attentive, and loving presence. In my home, they’ll enjoy a relaxed, pet-friendly environment with plenty of snuggles, play, and quiet time—whatever makes them feel safe and happy. If I’m coming to you, I aim to keep your pet’s routine as consistent as possible, respecting their space and energy. I treat every animal like family and always follow your instructions with care and attention to detail. We have a fenced in yard, and plenty of walkable sidewalks.
“Robert and Taylor were great and accommodated a last minute stay around the holidays. We got picture updates and our boy seemed like he had a great time. Highly recommend!!”
“Such a great sitter! She made me so comfortable leaving my babies with her and she checked in with me everyday with texts and photos. My dogs felt right at home and were treated like family. Highly recommend Gail for anyone looking for a reliable, caring dog sitter!”
“This was our first time leaving our puppy, and it seems that we weren't missed at all. James was very professional during the booking process, and was very thorough in making sure he understood everything he needed to know about Otis (who is very low maintenance, but I appreciated James' attention to detail.) I wish I had more to constructively report, but when everything goes exactly according to plan, all that remains for me to say is "Thanks, James!!!"”
“Was amazing all around. I know my dog enjoyed himself and her communication and picture updates were always fast and well needed given my 2 week separation from my fur baby. Will be reaching out again if I ever need a sitter!”
“This was my first time booking a sitter with Rover and I’m so glad I was able to find Reginald and Kelly to care for my pomchi Ruby! She absolutely loved them! They sent pics and videos of her during her stay and she looked so comfortable. I’m usually very nervous about leaving Ruby but seeing how well she was being cared for really helped to ease my anxiety. They’re such a nice couple and they really care about the pets they’re watching. I’ll definitely book with them again!!”
“Ashley and Dayan have the absolute sweetest family and they took the BEST care of my Koda. I was feeling worried leaving him as I was out of the country, but Ashley sent updates and pictures often which reassured me that he was in great hands. Ashely, Dayan, and their children loved on him so hard and gave him all the care and attention he needed!! They were very accommodating with keeping him separated from other dogs and taking him out multiple times a day. I will most definitely be using them again next time I need a sitter. Cannot thank your wonderful family enough! ❤️”
“We Had the pleasure of using Britanny to watch over our sweet millie and it was a great experience. Britanny made sure she kept us in the loop and put all of our worries to rest with updates,pics, Etc. Being that it was our first time ever using a sitter, she made our stay away from millie extremely pleasant. Thank you again Brittany. I would highly recommend.”
“Jennifer was great with Joy. She provided pictures of Joy and treated her as her own. I will be using Jennifer again. Thank you Jennifer for the lovely care for my fur baby Joy!!!”
Loving dog boarding sitters in your neighborhood
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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.
Wesley "Whitney" B.Star Sitter
“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.”
Rachel M.Star Sitter
“Rachel was great with Aspen. Her dogs and Aspen became fast friends very quickly. I received so many pictures it was delightful! When I ran out of time to bring Aspen to her, she was out not so far away and picked her up. Then was headed my way anyway, so returned her after I returned. Aspen will be very happy to go back as needed.”
Lisa R.
“Lisa was amazing and communicated often with pictures. She was very honest the throughout the stay and we will definitely be booking her again!”
Shelly S.Star Sitter
“Cannot say enough good things. My pup was living his best life. Shelly set up a puppy area for him. But he also got to run with the chickens. She clipped his nails and gave him a bath! He loves her and it made my trip better knowing that he was in such good hands.”
Angela & Bill C.Star Sitter
“Sophie was at Angela and Bill’s for two weeks. First time I have left her for that long. They sent photos and I felt reassured that she was doing ok. And they survived my 86 lb Bernedoodle.! Would highly recommend.”
Rachel C.Star Sitter
“The dogs had great time! Rachel handled our three dogs very well over the weekend, and we could tell they felt very comfortable with her. Highly recommend!”
Yvette W.
“Yvette was great with my 3 fur babies. She sent pictures and videos throughout the stay, which was very much appreciated. It was great knowing my babies were taken good care of while I was out of town. I will be booking with her whenever I need a sitter again.”
Melody & Matthew D.
“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!”
Emily H.
“Emily was professional and easy to communicate with. She took good care of the pups and sent us photos. We will contiinue to use her when we travel.”
Kimberly K.Star Sitter
“We felt safe with our dog there, and our dog seemed super contented being there. Kimberly was great with communication and photos—we’ve already booked her again!”
Megan L.
“Meghan was amazing! She sent a ton of pics and videos and really eased our mind with leaving our baby behind for the first time. Her and her family really went out of their way to make our furbaby feel at home. Meghan is kind and professional. You won’t find a better person to take care of your precious pup. She will absolutely be our go to in the future! Thanks again Meghan, so glad we found you!!”
Lauren K.
“Lauren is such a pet lover. When she visits my cats love to snuggle up on her, they even sleep with her at night (which is a rare honor from them) and she always respects both their personal boundaries and any rules I’ve set regarding food/treats. She loves animals of all kinds and is always ensuring she does her research if it’s an animal she’s not experienced before. She will love on your pets as if they were her own (and if they could write their own testimonials I’m sure they’d give her 5 stars) and I can’t think of anyone I’d trust more with my pets.”
Robert B.Star Sitter
“Robert and Taylor were great and accommodated a last minute stay around the holidays. We got picture updates and our boy seemed like he had a great time. Highly recommend!!”
Gail T.Star Sitter
“Such a great sitter! She made me so comfortable leaving my babies with her and she checked in with me everyday with texts and photos. My dogs felt right at home and were treated like family. Highly recommend Gail for anyone looking for a reliable, caring dog sitter!”
James C.Star Sitter
“This was our first time leaving our puppy, and it seems that we weren't missed at all. James was very professional during the booking process, and was very thorough in making sure he understood everything he needed to know about Otis (who is very low maintenance, but I appreciated James' attention to detail.) I wish I had more to constructively report, but when everything goes exactly according to plan, all that remains for me to say is "Thanks, James!!!"”
Kaitlynn H.
“Was amazing all around. I know my dog enjoyed himself and her communication and picture updates were always fast and well needed given my 2 week separation from my fur baby. Will be reaching out again if I ever need a sitter!”
Reginald & Kelly V.
“This was my first time booking a sitter with Rover and I’m so glad I was able to find Reginald and Kelly to care for my pomchi Ruby! She absolutely loved them! They sent pics and videos of her during her stay and she looked so comfortable. I’m usually very nervous about leaving Ruby but seeing how well she was being cared for really helped to ease my anxiety. They’re such a nice couple and they really care about the pets they’re watching. I’ll definitely book with them again!!”
Dayan & Ashley M.
“Ashley and Dayan have the absolute sweetest family and they took the BEST care of my Koda. I was feeling worried leaving him as I was out of the country, but Ashley sent updates and pictures often which reassured me that he was in great hands. Ashely, Dayan, and their children loved on him so hard and gave him all the care and attention he needed!! They were very accommodating with keeping him separated from other dogs and taking him out multiple times a day. I will most definitely be using them again next time I need a sitter. Cannot thank your wonderful family enough! ❤️”
Brittany J.
“We Had the pleasure of using Britanny to watch over our sweet millie and it was a great experience. Britanny made sure she kept us in the loop and put all of our worries to rest with updates,pics, Etc. Being that it was our first time ever using a sitter, she made our stay away from millie extremely pleasant. Thank you again Brittany. I would highly recommend.”
Jennifer E.
“Jennifer was great with Joy. She provided pictures of Joy and treated her as her own. I will be using Jennifer again. Thank you Jennifer for the lovely care for my fur baby Joy!!!”
Over 75 pet parents in Windsor have booked dog boarding
Windsor dog parents share their Rover experiences
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Select a filter and find qualifying Windsor sitters!How Rover works
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
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 Windsor is $35
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 Aug 2025, the median cost of dog boarding in Windsor is $35 per night, including service fees. Boarding your dog for one week typically costs $245. 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 $29 to as high as $49 per night.
As of Aug 2025, 311 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 311 dog boarding sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 100% 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.
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