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

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


“Amber was Fabulous with our pup🎉💐🎉!!!! She is very knowledgeable about dogs and their habits and mannerisms. A true Dog Whisperer!!!! Her communication while boarding was excellent and she sent daily videos and pictures of our little guy. We will definitely use Amber in the future and I fully recommend her.”


“Rebekah, was absolutely a great sitter for my Bucky. Daily pictures of how much fun and exercise she was given. Best part on pickup I could see how much fun he had since he was out in the yard playing with the other dogs. I would highly recommend her and will definitely use her again.”


“Kathryn was amazing! So warm and inviting to me and my dog Romeo! The kids loved on him just like he was their own. I got pics of him everyday and I’ve never seen a smile so big on his face! She made him feel at home and made me feel at ease knowing he was being taken care of in a safe and happy environment! This was my first time boarding him and I absolutely will be calling her in the future! 10/10!”


“Cynthia is definitely the best dog sitter I have met! Her and her family are incredibly sweet. My previous sitter canceled last minute and she responded and agreed to care for my Bailey at the last minute. I’m so grateful! Not only is she prompt with response, but she sent frequent updates and pictures. She has a big back yard and took Bailey on a fun excursion! Definitely worth the drive outside of Charlottesville! Will highly recommend!”


“Heather was absolutely amazing!! I couldn’t have asked for a better sitter to watch my fur baby! She has such a kind soul and her love for animals is so easy to feel and a joy to witness. She sent me daily updates, pictures and videos without me having to ask! My mind was at ease the whole time I was away and I know she ensured Booboo was comfortable as he could be. I can’t thank her enough. I’m so happy to have found her, she’s truly a gem 🩷”


“Jennifer was amazing! We are lucky to know her. I was surprised because my baby looked comfy and happy. (she has a little separate anxiety😢) We will back to her when we need a boarding again,👍🏻 I highly recommend!!”


“Julie and her family took great care of our dog Penny and treated her as their own. She had a spacious farm to roam and explore and other dogs to socialize with. This was the longest that we have left our dog but Julie provided regular updates of her visit. Our girl returned happy and tired!”


“Highly recommend Leah and Christopher for dog sitting! Finn felt right at home and loved running around their fenced yard. They were very helpful wi the my changing schedule and sent lots of pix of Finn! We will definitely ask to come back!”


“The moment we walked in for a meet and greet, we knew Heather and China were the perfect sitters for our pup, Teddy. Her boarding set up was awesome and very organized. Heather took every step she could to get to know our dog so that everything goes well during the stay. We received daily updates and photos of Teddy and the pack and we could tell that he received so much love and care from them! We highly recommend Heather’s hospitality and will book her for future boarding needs.”

“Nathan was wonderful! Very communicative and accommodating. Our pups had a ball, enjoyed great company and had no problems adjust to a new environment. Thanks to Nathan and his wife for being such a loving home away from home”


“I have to be very picky when choosing sitters as one pup has separation anxiety and will not stay with just anyone. I have had many issues with past sitters being dishonest and not following my guidance but I HIGHLY recommend Tanine!!! I have two very high energy pups (golden doodle and lab). She kept me updated, good and bad, and made sure to give my pup his meds with enough time for them to be effective prior to crating. She ensured to make them as comfortable as possible through the day and I truly appreciate her level of care. I specifically chose her due to the training background and I am so glad I followed through though there were not many reviews. I did not have to ask for pictures or updates throughout. She has small children that seem to love dogs so I know my pups received comfort as they love children. She is a gem! To have the patience and be willing to work with us through his anxiety is not something you find in all Rover sitters. Glad to have finally found a permanent option!”


“Whitney was so amazing with our dogs. This was our first time using Rover and she made the booking process smooth and simple. We were so comfortable leaving our girls with her. We got daily updates and photos of our dogs and the adventures they had the farm. We were at ease and able to enjoy our time away from home without any worries. I will be recommending her to our friends and we will be booking with her again.”


“We really like Jessica...she takes care of our senior girl so well. She sends updates and pics throughout her stay. We use her alot and Bella fits right in with her family.”


“What a great experience for my standard poodle! Jocelin was responsive and sent several pictures and texts about my girl during her stay. Drop off and pick up were also a breeze.”


About: I have owned dogs for my whole life. I have also fostered for the past 5+ years. I am well suited for any type of dog at any age. I am comfortable with special dietary needs, medications, Baths, walks, hikes ect. I am a stay at home mom of 11 year old twins, also animal lovers. I am self employed and have a very flexible schedule We do not have a fenced in yard however we live on a very private 12 acres with plenty of space for walks, hikes and adventure. I have 3 very well behaved dogs that know the rules! I do have crates and small playpen fences if required and am happy to make any necessary accommodations.
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.




Amber L.
Star Sitter


“Amber was Fabulous with our pup🎉💐🎉!!!! She is very knowledgeable about dogs and their habits and mannerisms. A true Dog Whisperer!!!! Her communication while boarding was excellent and she sent daily videos and pictures of our little guy. We will definitely use Amber in the future and I fully recommend her.”


Rebekah Y.
Star Sitter


“Rebekah, was absolutely a great sitter for my Bucky. Daily pictures of how much fun and exercise she was given. Best part on pickup I could see how much fun he had since he was out in the yard playing with the other dogs. I would highly recommend her and will definitely use her again.”


Kathryn M.Star Sitter

“Kathryn was amazing! So warm and inviting to me and my dog Romeo! The kids loved on him just like he was their own. I got pics of him everyday and I’ve never seen a smile so big on his face! She made him feel at home and made me feel at ease knowing he was being taken care of in a safe and happy environment! This was my first time boarding him and I absolutely will be calling her in the future! 10/10!”


Cynthia W.Star Sitter

“Cynthia is definitely the best dog sitter I have met! Her and her family are incredibly sweet. My previous sitter canceled last minute and she responded and agreed to care for my Bailey at the last minute. I’m so grateful! Not only is she prompt with response, but she sent frequent updates and pictures. She has a big back yard and took Bailey on a fun excursion! Definitely worth the drive outside of Charlottesville! Will highly recommend!”


Dana G.

“Our dog Maya had another wonderful visit with Dana. Dana sooooooo gets our Big Girl and it warms our hearts to know Maya is safe and well cared for and very much loved by Dana!”


Heather S.Star Sitter

“Heather was absolutely amazing!! I couldn’t have asked for a better sitter to watch my fur baby! She has such a kind soul and her love for animals is so easy to feel and a joy to witness. She sent me daily updates, pictures and videos without me having to ask! My mind was at ease the whole time I was away and I know she ensured Booboo was comfortable as he could be. I can’t thank her enough. I’m so happy to have found her, she’s truly a gem 🩷”


Jessica W.Star Sitter

“Jessica takes such good care of our corgi puppy! We never have to worry about leaving her in Jessica's care. I really appreciate all the pics and videos.”


Jennifer A.Star Sitter

“Jennifer was amazing! We are lucky to know her. I was surprised because my baby looked comfy and happy. (she has a little separate anxiety😢) We will back to her when we need a boarding again,👍🏻 I highly recommend!!”


Julie O.

“Julie and her family took great care of our dog Penny and treated her as their own. She had a spacious farm to roam and explore and other dogs to socialize with. This was the longest that we have left our dog but Julie provided regular updates of her visit. Our girl returned happy and tired!”


Leah & Christopher K.Star Sitter

“Highly recommend Leah and Christopher for dog sitting! Finn felt right at home and loved running around their fenced yard. They were very helpful wi the my changing schedule and sent lots of pix of Finn! We will definitely ask to come back!”


Heather M.

“The moment we walked in for a meet and greet, we knew Heather and China were the perfect sitters for our pup, Teddy. Her boarding set up was awesome and very organized. Heather took every step she could to get to know our dog so that everything goes well during the stay. We received daily updates and photos of Teddy and the pack and we could tell that he received so much love and care from them! We highly recommend Heather’s hospitality and will book her for future boarding needs.”


Nathan A.
Star Sitter


“Nathan was wonderful! Very communicative and accommodating. Our pups had a ball, enjoyed great company and had no problems adjust to a new environment. Thanks to Nathan and his wife for being such a loving home away from home”


Tanine D.

“I have to be very picky when choosing sitters as one pup has separation anxiety and will not stay with just anyone. I have had many issues with past sitters being dishonest and not following my guidance but I HIGHLY recommend Tanine!!! I have two very high energy pups (golden doodle and lab). She kept me updated, good and bad, and made sure to give my pup his meds with enough time for them to be effective prior to crating. She ensured to make them as comfortable as possible through the day and I truly appreciate her level of care. I specifically chose her due to the training background and I am so glad I followed through though there were not many reviews. I did not have to ask for pictures or updates throughout. She has small children that seem to love dogs so I know my pups received comfort as they love children. She is a gem! To have the patience and be willing to work with us through his anxiety is not something you find in all Rover sitters. Glad to have finally found a permanent option!”


Christine L.

“Oakley came back happy and tired. Communication was great, and he even enjoyed the fact that he got to run and play with other dogs. I will be using Christine again.”


Marianne S.

“Marianne was the perfect sitter for dewey. He was so comfortable and spoiled. I couldn't ask for a better experience for him!! She will be Dewey's go to sitter!”


Whitney G.

“Whitney was so amazing with our dogs. This was our first time using Rover and she made the booking process smooth and simple. We were so comfortable leaving our girls with her. We got daily updates and photos of our dogs and the adventures they had the farm. We were at ease and able to enjoy our time away from home without any worries. I will be recommending her to our friends and we will be booking with her again.”


Jessica C.Star Sitter

“We really like Jessica...she takes care of our senior girl so well. She sends updates and pics throughout her stay. We use her alot and Bella fits right in with her family.”


Lakeshia W.Star Sitter

“Lakeisha was great. Always kept me up to date on my pet and sending plenty of pictures”


Jocelin B.Star Sitter

“What a great experience for my standard poodle! Jocelin was responsive and sent several pictures and texts about my girl during her stay. Drop off and pick up were also a breeze.”


Devon R.
“Devon is a knowledgeable, responsible and compassionate person who will care for your animals as if they are her own! Devon has cared for both my fur babies and human children. She has loads of animal caregiving experience. Everyone and anyone would be lucky to have Devon caring for their pets!”
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
As of Aug 2025, 128 sitters provided dog boarding in Winfrey. 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 Winfrey dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winfrey have an average of 20 years of experience. Dog boarding sitters with repeat customers have an average of 10 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 Winfrey.
Rover makes it easy to find Winfrey 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 128 dog boarding sitters in Winfrey on Rover, so you’re sure to find the perfect match for your dog! In Winfrey, 92% of sitters offer daily exercise, 100% offer medication administration, and 100% 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.
