Dog Boarding in Wintergreen, VA
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Wintergreen dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Our pup had a wonderful stay with Hillary! We receive daily updates with photos. Our girl was given walks and lots of love and had a fun time while we were away! Thank you!”
“Amy took such great care of our dog while we were away. This was our first time leaving him with anyone after adopting him this Fall. We were gone for 10 days and each day Amy sent pictures and videos and was incredible at communicating. Which helped us know how he was doing and he did great! Will definitely come back and highly recommend booking with her!”
“Maui’s stay with Hannah was awesome. From the moment I dropped my dog off, I could tell that Hannah was a total animal lover and that Maui was going to be in great hand My dog has anxiety issues and Hannah was great at administering his meds. Hannah sent many pictures to show me how happy Maui was during his stay. I will definitely check with Hannah again when going away and need an amazing dog sitter.”
“Nadia was absolutely fantastic. We received daily updates on how our dog was doing and knew that she was very well taken care of. Nadia ensures that the dogs under her care get plenty of exercise/outside time and receive oodles of affection. I would highly recommend her!”
“Merlin had a wonderful time at Andrew’s! He sent updates at least once a day and took Merlin outside to play and expel his super high energy. I highly recommend Andrew for anyone needing care for their pet! He was very professional and was super knowledgeable about behavior recognition and training! His two dogs, Zeus and Baloo, are super sweet and interacted with Merlin very well.”
“Jani and Paul treated Leo like he was part of the family. He received so much attention and love, I’m not sure he wanted to leave! Thank you so much for giving Leo such wonderful care.”
“Bree was great with Winter! She sent all the pictures and was really responsive. I had some travel changes and she was very accommodating for picking Winter up at a different time. Will definitely use Bree again if I need a sitter in Charlottesville!”
“Jackie was amazing when watching our dog for 2.5 weeks while we were out of the country. She had great communication and sent us pics throughout the time. Great location as well for dogs to stay! Our dog has 3 legs and Jackie had no issues watching our dog and was very accommodating with any special needs. Highly recommend Jackie!”
“Highly recommend these two, they were so nice and welcoming. My dog looked right at home with them and I had no worries. They send updates and pictures! Would book again!!”
“Casey was amazing with our three large dogs. They can be very high energy and a lot to handle at times. One of our pups has separation anxiety away from home but he seemed to do soooo well with Casey. And she was so attentive to all their needs. She did a wonderful job with all three of them and their crazy personalities. She took them on lots of walks. We loved the picture updates. It made us so happy that our pups seemed so content on their vacation away from home. We will definitely rebook in the future! Thanks so much, Casey!!!”
About: Ive grown up with animals and took an interest in training and sitting when I was around 10 years old. I have experience training and watching family dogs, reactive dogs, service dogs and puppies! I also have multiple animals of my own and am well versed in the different care that different species may need. When I am home, my attention is 100% on my animals. I do have a full time job in a neighboring city and am gone for normal work hours, but devote time and attention when I am home. In my own home, everybody has their own space. With dogs, cats and bunnies, each animal has the ability to socialize or spend time on their own in their space. Each animal has been trained to appropriately interact with each other.
“Penny was absolutely wonderful! She sent lots of updates and pictures of our doggie and made us feel completely comfortable leaving our dog for the first time! We will definitely use her again in the future!”
“Deb was great! We originally book with just one dog for the weekend of our wedding and ended up getting a second one and she was willing to watch them both. She was flexible with us to let us come pick them up to have them be included in some pictures. We got lots of updates and they had a good time. We will definitely book again if we are in the area.”
“Svitlana was so great with Birdie. She sent updates and pictures which really set our mind at ease because Birdie isn't used to being away from us for a long weekend. She took Birdie on walks and let her chill on the couch. Thanks for all your care with Birdie!”
“We were nervous leaving our 6-month-old puppy for the first time, but Cory made it a wonderful experience for us and our pup. Cory was easy to communicate with; he provided lots of photos and updates when we were gone and Riley seemed very happy and content when we went to pick her up. We would definitely like to have Cory watch Riley again.”
“Nothing short of AMAZING!! Very accommodating and always takes great care of our sweet girl and provides updates throughout the day. We couldn’t be happier with services we received.”
“Brooke truly took care of my dog Peter and he was happy and calm when picked. He liked to stay with Brooke and had good time playing in dog park. We felt Peter is in best hands and Brooke made us comfortable, she is very responsive and took good care of our dog. I highly recommend Brooke and would surely visit again.”
“Eman is absolutely amazing! She has watched our fur baby, Simmi, multiple times, and every single time has been a fantastic experience. Simmi gets so excited when we’re approaching her house, her tail starts wagging nonstop! It’s clear how much love and care Eman gives her. We feel completely at ease knowing Simmi is in such good hands. Reliable, kind, and attentive and is truly the only one I trust to watch Simmi 💕💕”
Loving dog boarding sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Hillary D.Star Sitter
“Our pup had a wonderful stay with Hillary! We receive daily updates with photos. Our girl was given walks and lots of love and had a fun time while we were away! Thank you!”
Amy H.Star Sitter
“Amy took such great care of our dog while we were away. This was our first time leaving him with anyone after adopting him this Fall. We were gone for 10 days and each day Amy sent pictures and videos and was incredible at communicating. Which helped us know how he was doing and he did great! Will definitely come back and highly recommend booking with her!”
Hannah H.Star Sitter
“Maui’s stay with Hannah was awesome. From the moment I dropped my dog off, I could tell that Hannah was a total animal lover and that Maui was going to be in great hand My dog has anxiety issues and Hannah was great at administering his meds. Hannah sent many pictures to show me how happy Maui was during his stay. I will definitely check with Hannah again when going away and need an amazing dog sitter.”
Nadia G.
“Nadia was absolutely fantastic. We received daily updates on how our dog was doing and knew that she was very well taken care of. Nadia ensures that the dogs under her care get plenty of exercise/outside time and receive oodles of affection. I would highly recommend her!”
Andrew S.
“Merlin had a wonderful time at Andrew’s! He sent updates at least once a day and took Merlin outside to play and expel his super high energy. I highly recommend Andrew for anyone needing care for their pet! He was very professional and was super knowledgeable about behavior recognition and training! His two dogs, Zeus and Baloo, are super sweet and interacted with Merlin very well.”
Jani & Paul R.Star Sitter
“Jani and Paul treated Leo like he was part of the family. He received so much attention and love, I’m not sure he wanted to leave! Thank you so much for giving Leo such wonderful care.”
Bree L.
“Bree was great with Winter! She sent all the pictures and was really responsive. I had some travel changes and she was very accommodating for picking Winter up at a different time. Will definitely use Bree again if I need a sitter in Charlottesville!”
Jackie B.
“Jackie was amazing when watching our dog for 2.5 weeks while we were out of the country. She had great communication and sent us pics throughout the time. Great location as well for dogs to stay! Our dog has 3 legs and Jackie had no issues watching our dog and was very accommodating with any special needs. Highly recommend Jackie!”
Gretchen R.
“Walker had a great time with Gretchen and Gizmo! Thanks you for hosting him”
Jesse & Emily H.Star Sitter
“Highly recommend these two, they were so nice and welcoming. My dog looked right at home with them and I had no worries. They send updates and pictures! Would book again!!”
Casey L.
Star Sitter
“Casey was amazing with our three large dogs. They can be very high energy and a lot to handle at times. One of our pups has separation anxiety away from home but he seemed to do soooo well with Casey. And she was so attentive to all their needs. She did a wonderful job with all three of them and their crazy personalities. She took them on lots of walks. We loved the picture updates. It made us so happy that our pups seemed so content on their vacation away from home. We will definitely rebook in the future! Thanks so much, Casey!!!”
Jocelyn A.
“Josie walked and trained my little Pomeranian for most of the summer. She taught him how to sit, stay, wait at the door, and to walk nicely on the leash. She gave me tips on how to care for him. She is great!”
Penny H.Star Sitter
“Penny was absolutely wonderful! She sent lots of updates and pictures of our doggie and made us feel completely comfortable leaving our dog for the first time! We will definitely use her again in the future!”
Deb K.Star Sitter
“Deb was great! We originally book with just one dog for the weekend of our wedding and ended up getting a second one and she was willing to watch them both. She was flexible with us to let us come pick them up to have them be included in some pictures. We got lots of updates and they had a good time. We will definitely book again if we are in the area.”
Svitlana F.Star Sitter
“Svitlana was so great with Birdie. She sent updates and pictures which really set our mind at ease because Birdie isn't used to being away from us for a long weekend. She took Birdie on walks and let her chill on the couch. Thanks for all your care with Birdie!”
Cory P.Star Sitter
“We were nervous leaving our 6-month-old puppy for the first time, but Cory made it a wonderful experience for us and our pup. Cory was easy to communicate with; he provided lots of photos and updates when we were gone and Riley seemed very happy and content when we went to pick her up. We would definitely like to have Cory watch Riley again.”
Margaret M.
“Margaret was very kind and sweet to take care of Blaze on a quick notice. She sent us updates without being asked. We will use her again! Thank you!!!”
Bertie A.Star Sitter
“Nothing short of AMAZING!! Very accommodating and always takes great care of our sweet girl and provides updates throughout the day. We couldn’t be happier with services we received.”
Brooke L.Star Sitter
“Brooke truly took care of my dog Peter and he was happy and calm when picked. He liked to stay with Brooke and had good time playing in dog park. We felt Peter is in best hands and Brooke made us comfortable, she is very responsive and took good care of our dog. I highly recommend Brooke and would surely visit again.”
Eman W.Star Sitter
“Eman is absolutely amazing! She has watched our fur baby, Simmi, multiple times, and every single time has been a fantastic experience. Simmi gets so excited when we’re approaching her house, her tail starts wagging nonstop! It’s clear how much love and care Eman gives her. We feel completely at ease knowing Simmi is in such good hands. Reliable, kind, and attentive and is truly the only one I trust to watch Simmi 💕💕”
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!
Why Choose Rover?
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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
As of Aug 2025, 119 sitters provided dog boarding in Wintergreen. 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, 93% of Wintergreen dog boarding sitters respond in under an hour.
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 Wintergreen.
Rover makes it easy to find Wintergreen 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 119 dog boarding sitters in Wintergreen on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific 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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