Dog Boarding in Windsor, Richmond, 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.


“Very carrying and dependable. Kept us informed each day by providing us pictures of our beloved dog. Will use her again for sure. Bentley came home happy & no stress.”


“We love having Matt take over my sweet girl while we are out of town. He always does a great job!! Absolutely love all the pictures and updates - thank you Matt!!”


“Initially, I was worried about leaving my sweet boy, Murphy, with anyone as he's never been without me. However, he had the time of his life; his own mini vacation. Royal & Rhonda provided lots of updates with pictures and comments. In every picture he had the biggest smile. It made me so happy to see him having such a great time interacting with the family. I highly recommend Royal & Rhonda and will definitely use them again!”


“My fur-child Jetson had a great 4 day stay at Julie"s place. She kept my mind at ease by sending lots of updates and pictures while he was in her care. She also was great at making sure he stayed on his medication and letting me know exactly how she was handling his anxiety and health concerns. I was so comfortable with her care of him and will be sure to book her again in the future!”


“It was our first time leaving our dog Lucy with Michelle and Lucy had a wonderful time and Michelle took great care of of her. I really appreciated the daily updates and pictures on how Lucy was doing. We were gone for a week and I felt comfortable and confident leaving Lucy in her care. I highly recommend her to anyone looking for a great dog sitter!”


“Myrna was great with our dog Archie!! She's very experienced with watching dogs and her house seems like a great environment for dogs to have a great time. I'd highly recommend her!”


“Alexandra boarded our 14 year old super senior pug and she did really well. She used to go to a large boarding facility and when she came home she was very out of sorts and unsettled. Diamond came right back home and settled right back in so it seems that she was happy while we were gone. Alexandra was super responsive and sent daily updates. Overall it was a great experience for us and apparently for her as well :)”


“Roscoe had the best time playing with friends. He was so well taken care of. I received so many pictures and videos. Raye is awesome and Roscoe was in great hands.”


“Danielle was awesome! She accommodated me pretty last minute when travel plans changed and made it super easy to schedule a meet and greet. Her dogs were well-behaved and played great with my dog. She was super communicative while I was gone and accommodating with pickup. Amazing sitter and I’ll definitely be using her again!”



“Hilary was great with Venus! Her communication was also second to none! I'm glad we found each other because our doggy will be going back! Highly recommend leaving your dog with Hilary - you will not be disappointed!”


“Nicole kept us up to date with pictures and letting us know Maui was comfortable and at peace. We loved how she worked with us on our return and was especially ready when we arrived. Thank you again Nicole, Maui really enjoyed you this weekend!”


“Jeffrey was fantastic with my dog! He sent me lots of updates and pictures while I was away, so I was always confident that Malcolm was being well taken care of. I also appreciated that Jeffrey was happy to take Malcolm on good walks and also cuddle with him when they were just hanging out. I highly recommend this Rover!”


“Kat was absolutely amazing with my highly reactive and mildly difficult girl! I gave her a heads up with Bindi’s behaviors and she assured me everything would would be alright. When I dropped Bindi off, Kat even let me in to see how my pup interacts with hers and her pups are absolutely wonderful with others! When I come back to Tuscon I will definitely be reaching out!”



“Tiffany is amazing! This was the first time I boarded my Simba. I was so nervous. However, Simba was very well taken care of. Tiffany kept me updated with texts and pictures. She was professional and caring toward not only Simba but me as well. Simba truly enjoyed his stay. I don’t think he wanted to come home! I will definitely use Tiffany’s services again. If you want a reliable, patient, caring, and professional person to care for your pet, Tiffany is your person!!!”


About: Experience caring for dogs in all ages and stages. Comfortable giving medications, following special diets, and anything else to keep your dog healthy and happy. I work full-time Monday-Friday, but am available in the evenings and weekends. I’m okay with adding additional furry members to my household while you travel and/or dropping in to check on them in the comfort if their own home. Full disclaimer: I have a senior dog, a cat, and school-aged children. Everyone in my household is friendly with both dogs and cats. My yard is fenced (4ft, chain-link) and dogs have access to a screened in porch if they prefer staying outdoors during the day. I’m more than happy to keep them inside, either crated or not, depending on your preferences.

“Michaela was AMAZING! So sweet and attentive to Violet, and sent lots of updates and pictures throughout the stay, which gave us so much peace of mind. She administered Violet’s medications and special food three times a day with no issues and made everything feel effortless. Michaela was also very easy to schedule with and super responsive with communication. We’re so grateful to have found her and will definitely be booking with her again!”


About: With over 7 years of hands-on experience as a devoted pet owner, I’ve cared for animals at every life stage—from the gentle needs of my senior toy poodle to the boundless energy of my young golden retriever. I specialize in creating a nurturing and safe environment, offering personalized care that includes potty training, leash walking, and reinforcing basic obedience commands like sit, stay, and recall. Whether it’s meeting the unique challenges of senior care or keeping active pups engaged, I bring patience, attentiveness, and a deep passion for happy, healthy pets. As someone who works from home with a flexible schedule, pet care naturally fits into my daily routine. I’m able to provide consistent attention throughout the day, from morning walks and feeding to playtime and enrichment activities. My flexible schedule ensures your pets receive the care and attention they need, with plenty of time for exercise, training, and affection. In my home, I provide designated spaces for my pets to rest and play, ensuring they have a comfortable and secure area. I also have a fenced yard where pets can safely enjoy outdoor time. Your pet will be safe and comfortable, and if they enjoy playing with other dogs, I can arrange playtime with mine. If preferred, I can keep pets separate or crate them if they are crate-trained, ensuring everyone feels relaxed. I follow a consistent routine for my dogs, including regular feeding, walks, and playtime, to maintain a sense of structure. Whether in my home or yours, I focus on creating a safe and positive environment where pets feel at ease, with plenty of attention and affection throughout their stay.

“Ross and Ava took great care of our old girl. They sent us updates regularly and were flexible on pick up time. We’ll definitely be booking with them again!”

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.


Amy M.


“Amy is truly wonderful with Prince. He has met new friends and loves being with Amy for daycare and bordering. She treats him like family. She’s the best!”




DAMACIA J.Star Sitter

“Very carrying and dependable. Kept us informed each day by providing us pictures of our beloved dog. Will use her again for sure. Bentley came home happy & no stress.”


Matt M.Star Sitter

“We love having Matt take over my sweet girl while we are out of town. He always does a great job!! Absolutely love all the pictures and updates - thank you Matt!!”


Royal & Rhonda P.Star Sitter

“Initially, I was worried about leaving my sweet boy, Murphy, with anyone as he's never been without me. However, he had the time of his life; his own mini vacation. Royal & Rhonda provided lots of updates with pictures and comments. In every picture he had the biggest smile. It made me so happy to see him having such a great time interacting with the family. I highly recommend Royal & Rhonda and will definitely use them again!”


Julie W.
Star Sitter


“My fur-child Jetson had a great 4 day stay at Julie"s place. She kept my mind at ease by sending lots of updates and pictures while he was in her care. She also was great at making sure he stayed on his medication and letting me know exactly how she was handling his anxiety and health concerns. I was so comfortable with her care of him and will be sure to book her again in the future!”


Michelle T.Star Sitter

“It was our first time leaving our dog Lucy with Michelle and Lucy had a wonderful time and Michelle took great care of of her. I really appreciated the daily updates and pictures on how Lucy was doing. We were gone for a week and I felt comfortable and confident leaving Lucy in her care. I highly recommend her to anyone looking for a great dog sitter!”


Myrna C.Star Sitter

“Myrna was great with our dog Archie!! She's very experienced with watching dogs and her house seems like a great environment for dogs to have a great time. I'd highly recommend her!”


Alexandra O.Star Sitter

“Alexandra boarded our 14 year old super senior pug and she did really well. She used to go to a large boarding facility and when she came home she was very out of sorts and unsettled. Diamond came right back home and settled right back in so it seems that she was happy while we were gone. Alexandra was super responsive and sent daily updates. Overall it was a great experience for us and apparently for her as well :)”


Raye J.Star Sitter

“Roscoe had the best time playing with friends. He was so well taken care of. I received so many pictures and videos. Raye is awesome and Roscoe was in great hands.”


Danielle K.Star Sitter

“Danielle was awesome! She accommodated me pretty last minute when travel plans changed and made it super easy to schedule a meet and greet. Her dogs were well-behaved and played great with my dog. She was super communicative while I was gone and accommodating with pickup. Amazing sitter and I’ll definitely be using her again!”




Hilary R.
Star Sitter


“Hilary was great with Venus! Her communication was also second to none! I'm glad we found each other because our doggy will be going back! Highly recommend leaving your dog with Hilary - you will not be disappointed!”


Nicole B.Star Sitter

“Nicole kept us up to date with pictures and letting us know Maui was comfortable and at peace. We loved how she worked with us on our return and was especially ready when we arrived. Thank you again Nicole, Maui really enjoyed you this weekend!”


Jeffrey H.Star Sitter

“Jeffrey was fantastic with my dog! He sent me lots of updates and pictures while I was away, so I was always confident that Malcolm was being well taken care of. I also appreciated that Jeffrey was happy to take Malcolm on good walks and also cuddle with him when they were just hanging out. I highly recommend this Rover!”


Lauren B.

“Lauren was willing to take Leo on short notice and she did amazing. She gave me a bunch of pictures of him and kept me updated. Would definitely bring Leo back”


Kat R.

“Kat was absolutely amazing with my highly reactive and mildly difficult girl! I gave her a heads up with Bindi’s behaviors and she assured me everything would would be alright. When I dropped Bindi off, Kat even let me in to see how my pup interacts with hers and her pups are absolutely wonderful with others! When I come back to Tuscon I will definitely be reaching out!”




Tiffany B.
Star Sitter


“Tiffany is amazing! This was the first time I boarded my Simba. I was so nervous. However, Simba was very well taken care of. Tiffany kept me updated with texts and pictures. She was professional and caring toward not only Simba but me as well. Simba truly enjoyed his stay. I don’t think he wanted to come home! I will definitely use Tiffany’s services again. If you want a reliable, patient, caring, and professional person to care for your pet, Tiffany is your person!!!”


Amber B.Star Sitter
About: Experience caring for dogs in all ages and stages. Comfortable giving medications, following special diets, and anything else to keep your dog healthy and happy. I work full-time Monday-Friday, but am available in the evenings and weekends. I’m okay with adding additional furry members to my household while you travel and/or dropping in to check on them in the comfort if their own home. Full disclaimer: I have a senior dog, a cat, and school-aged children. Everyone in my household is friendly with both dogs and cats. My yard is fenced (4ft, chain-link) and dogs have access to a screened in porch if they prefer staying outdoors during the day. I’m more than happy to keep them inside, either crated or not, depending on your preferences.


Michaela Z.Star Sitter

“Michaela was AMAZING! So sweet and attentive to Violet, and sent lots of updates and pictures throughout the stay, which gave us so much peace of mind. She administered Violet’s medications and special food three times a day with no issues and made everything feel effortless. Michaela was also very easy to schedule with and super responsive with communication. We’re so grateful to have found her and will definitely be booking with her again!”


Miguel A.
“Miguel is an exceptional dog handler and loving caregiver. His patience, reliability, and genuine care ensure dogs feel safe, happy, and truly loved under his watch. He has a natural ability to connect with dogs, ensuring their comfort and well-being. Miguel’s professionalism and dedication make him a trustworthy choice for any pet parent. Miguel goes above and beyond in his care, treating every dog as if they were his own. I wholeheartedly recommend him for his unmatched dedication and kindness.”


Ross & Ava T.Star Sitter

“Ross and Ava took great care of our old girl. They sent us updates regularly and were flexible on pick up time. We’ll definitely be booking with them again!”
Windsor dog parents share their Rover experiences
Kyla is a true gem! She cared for our pup KoKo for 12 days—his very first time away from us—and we couldn’t have asked for a more loving, attentive sitter. She helped him make new furry friends, took him on fun and stimulating walks, and even spent quiet time with him by the pool. Her gentle care and light training gave KoKo confidence and joy. When we picked him up, we could tell he’d had a blast and felt safe. Kyla’s home became a peaceful second home for our little guy. No wonder she’s a Star Sitter—we see why! Truly looking forward to using her services again and again!

Amber and Jason took such amazing care of our little puppy. It was the first time we had left her with anyone, and she’s tiny, but they did everything to be accommodating and safe with her. They also sent lots of videos, pictures. and updates. I was able to get away and unplug for a much-needed relaxing weekend. Thanks a million!

Tyler and her dog Bowie are wonderful. Tyler sent me frequent updates and pictures which helped ease my mind about leaving my dog who struggles with separation. She is a fantastic sitter and took great care of him. She made sure he was comfortable throughout the entire visit. I would absolutely recommend her to anyone who is looking for a sitter who loves and understands dogs! She is great!

Popular requests near you
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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available 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
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.
