Dog Boarding in Winesap, VA
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winesap dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Tank was brought back to us excited and happy. I could tell he was well taken care of. We loved the "doggy" bag that was given with the cutest picture of our boy! We will definitely use Courtney in the future.”
“This is our second time using Casey as our dogs vacation when we go on vacation. We can tell our dog loves it through the constant photo updates she sends ♥️ she truly takes care of our dog like we would and makes her part of the family. We are so glad to have found our sitter for our girl! Thank you Casey can't wait to book you 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 💕💕”
“We felt a little apprehensive using rover until we met with Brenda. After meeting her we new our Maltipoo Snickers would be fine. She kept him for 9 days and we received daily pictures and updates. her home is very dog friendly with a large shaded and fenced in yard. We would not hesitate to recomend Brenda.”
“Wendy was very reassuring while keeping Sammy. I had only had Sammy for 3 weeks when I needed a sitter for a day and a half. I was very nervous to leave him. Wendy kept me updated with photos while keeping Sammy which really helped me. Wendy has a big fenced in back yard which is also very nice for a puppy or grown dog. I was fortunate she had another puppy arrive the second day so my puppy had someone to play with! :-) I would recommend Wendy as a pet sitter if you find your self in need. She has a lot of experience especially with puppies! You can also read the rest of her reviews as I did which brought me to her in the first place!”
“I cannot say enough about Krystal and her family! Truly the best dog sitter I could ever dream up!! She loved our sweet poochie like her own! She sent me daily updates with pictures and details about how he was doing, and what fun activities they were doing with him! She has a gorgeous area in her home dedicated to doggy sitting, and it is just lovely. They took him on walks and puppy stroller rides when the pavement was too hot for his little feet. They worked on his tricks with him, they even bought him a new toy just for the fun of it! I had no doubts that he was being well cared for, and that was so comforting to me while we were traveling. I will 100% use Krystal again, and recommend her to everyone!!”
“Falcor enjoyed his Christmas vacation with Carla. She sent us updates and pictures every day. He ran out of food and she made sure to let us know and went and got him what he needed. We would recommend Carla to anyone needing a dog sitter for an extended trip.”
“Very highly recommended! Chantal and her husband were great caretakers for our two dogs for a week’s time — even more than we could have expected. They have a beautiful, spacious, safe place — both indoors and for when they had to go outside. My husband and I felt 100% comfortable leaving them there while we were away. From the beginning during our meet-and-greet through pick-up at the end of our trip, we saw just how kind and calm they were, treating our dogs just like their own dog and providing lots of interaction and play. Also, Chantal was extremely accommodating of our 7 month old puppy’s “puppy behavior” and attentive to the need to go outside more frequently. She provided updates every day (and was very responsive to other questions) and we could see just how relaxed our pups were, as if they were staying with family. We are definitely planning on using Chantal’s services the next time we need to go out of town.”
“Sofia was fantastic—super accommodating and flexible, very communicative, and such a sweet and gentle caregiver for my kitty. I boarded Kiwi with her for a week on super short noticed, and she was willing to go above and beyond with pick up / drop off, daily medicine giving, and regular photo updates. I wish she lived in Boston year-round so that she could be my go-to sitter when I’m away for work trips! I’d 10/10 recommend Sofia to anyone looking for a Rover sitter!”
“This was my first time leaving Goose with someone I didn’t know and Falen made it so easy! Updated me along the way with pics and videos and was so easy to check in with. I would 100 percent use her again and so thankful to be able to leave him with someone who loves on him like I would!”
About: I've had dogs for my whole life and I absolutely love them. I love all dogs too, big or small. I love playing with them and running and walking them. Dog cuddles are definitely the best to me. I am currently a preschool teacher, but I will be done each day around 12:30. My hours are flexible, especially in the summer and during school breaks. I am able to work around all kinds of schedules at this time. I have my own dog and I take her on multiple walks daily and make sure to play with her too and make sure that she gets plenty of daily exercise. I also walk my neighbors two dogs daily Monday-Friday and make sure that they get good exercise and go potty for her in the middle of each day. I have even done check in visits with another one of my neighbors that have cats and I made sure to clean their litter boxes and refresh any empty food bowls or water bowls too while they were out of town.
About: I have loved animals since I was a little girl. Having grown up around dogs of all sizes, I’m committed to taking the best care of your fur baby. I know how important it is to find someone you can trust! I currently work from home all week & am available pretty much all day for potty breaks, feedings and play time! I live near a lot of trails and I love walking companions! I have one small dog who would absolutely love a play partner. I live in a very walkable location and my husband and I are constantly taking our dog for walks, another companion would be great! My schedule is so flexible so I am able to accommodate any specific needs!
“Joelle was amazing! She was super communicative the whole time and sent many cute pictures and updates. It was clear my cat was comfortable and well cared for, which means so much to me. I really appreciate how thoughtful and reliable she was. I’ve already booked her again and wouldn’t hesitate to recommend her to anyone!”
“This wonderful lady was very willing to help us out and she went above and beyond for our dog Emma. After a couple pouty moments emma finally settled in and had a blast playing with the other Dog I will rebook with her if we both have mutual dates. Please allow her to watch your pets”
“I was a nervous wreck! John and his fiancée were wonderful hosts for my 2 large, spoiled dogs. The dogs had access to their home and a huge backyard. I got photos and updates, daily. The dogs came back happy and tired. Will definitely use them again!”
“Alexis watched my dog Cassie while I was in town for a few days. She was communicative in the lead up and during the stay. She took great care of Cassie and I would definitely book with her again next time I'm in town.”
“Rebecca and her family provided a loving home for the weekend while we were away! Their two dogs were very gentle and sweet and my dogs loved playing with them. Her kids are also great. We look forward to booking again!”
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.
Cortney S.Star Sitter
“Tank was brought back to us excited and happy. I could tell he was well taken care of. We loved the "doggy" bag that was given with the cutest picture of our boy! We will definitely use Courtney in the future.”
Casey L.
Star Sitter
“This is our second time using Casey as our dogs vacation when we go on vacation. We can tell our dog loves it through the constant photo updates she sends ♥️ she truly takes care of our dog like we would and makes her part of the family. We are so glad to have found our sitter for our girl! Thank you Casey can't wait to book you 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 💕💕”
Brenda M.
“We felt a little apprehensive using rover until we met with Brenda. After meeting her we new our Maltipoo Snickers would be fine. She kept him for 9 days and we received daily pictures and updates. her home is very dog friendly with a large shaded and fenced in yard. We would not hesitate to recomend Brenda.”
Wendy D.
“Wendy was very reassuring while keeping Sammy. I had only had Sammy for 3 weeks when I needed a sitter for a day and a half. I was very nervous to leave him. Wendy kept me updated with photos while keeping Sammy which really helped me. Wendy has a big fenced in back yard which is also very nice for a puppy or grown dog. I was fortunate she had another puppy arrive the second day so my puppy had someone to play with! :-) I would recommend Wendy as a pet sitter if you find your self in need. She has a lot of experience especially with puppies! You can also read the rest of her reviews as I did which brought me to her in the first place!”
Krystal S.
“I cannot say enough about Krystal and her family! Truly the best dog sitter I could ever dream up!! She loved our sweet poochie like her own! She sent me daily updates with pictures and details about how he was doing, and what fun activities they were doing with him! She has a gorgeous area in her home dedicated to doggy sitting, and it is just lovely. They took him on walks and puppy stroller rides when the pavement was too hot for his little feet. They worked on his tricks with him, they even bought him a new toy just for the fun of it! I had no doubts that he was being well cared for, and that was so comforting to me while we were traveling. I will 100% use Krystal again, and recommend her to everyone!!”
Carla M.
“Falcor enjoyed his Christmas vacation with Carla. She sent us updates and pictures every day. He ran out of food and she made sure to let us know and went and got him what he needed. We would recommend Carla to anyone needing a dog sitter for an extended trip.”
Emily L.
“Emily watched Bear and did a great job communicating and sending photos of Bear. Bear enjoyed staying with Emily and I will definitely rebook future visits.”
Aquilla F.Star Sitter
“Fantastic service! Riley had such a good time and I got the cutest photo updates. Was super flexible when I unexpectedly had to extend a day. 11/10!”
Chantal E.
“Very highly recommended! Chantal and her husband were great caretakers for our two dogs for a week’s time — even more than we could have expected. They have a beautiful, spacious, safe place — both indoors and for when they had to go outside. My husband and I felt 100% comfortable leaving them there while we were away. From the beginning during our meet-and-greet through pick-up at the end of our trip, we saw just how kind and calm they were, treating our dogs just like their own dog and providing lots of interaction and play. Also, Chantal was extremely accommodating of our 7 month old puppy’s “puppy behavior” and attentive to the need to go outside more frequently. She provided updates every day (and was very responsive to other questions) and we could see just how relaxed our pups were, as if they were staying with family. We are definitely planning on using Chantal’s services the next time we need to go out of town.”
Izza Sofia H.Star Sitter
“Sofia was fantastic—super accommodating and flexible, very communicative, and such a sweet and gentle caregiver for my kitty. I boarded Kiwi with her for a week on super short noticed, and she was willing to go above and beyond with pick up / drop off, daily medicine giving, and regular photo updates. I wish she lived in Boston year-round so that she could be my go-to sitter when I’m away for work trips! I’d 10/10 recommend Sofia to anyone looking for a Rover sitter!”
Falen F.Star Sitter
“This was my first time leaving Goose with someone I didn’t know and Falen made it so easy! Updated me along the way with pics and videos and was so easy to check in with. I would 100 percent use her again and so thankful to be able to leave him with someone who loves on him like I would!”
Christin G.Star Sitter
“Chrissy is an amazing person. She takes such great care of everything in her life to the greatest detail. Her 1 year old pup, Alice, is the cutest, sweetest thing ever. She already has been taking care of other dogs in her neighborhood in her free time for quite a while. Anyone who employees Chrissy’s services will surely be more than satisfied!”
Alexis K.
“I can’t say enough good things about Lexie! From the moment we connected, she was communicative, thoughtful, and incredibly professional. Most importantly—she took absolutely outstanding care of my dog. Throughout the stay, I received regular updates, photos, and even a few videos, which gave me complete peace of mind. My dog can be a little anxious in new environments, but Lexie treated her like family—patient, attentive, and full of love. When I picked up my pup, she was relaxed, happy, and clearly well cared for. It’s not easy to trust someone with your fur baby, but Lexie has earned my full trust and gratitude. I wouldn’t hesitate to book with her again!”
Joelle L.
“Joelle was amazing! She was super communicative the whole time and sent many cute pictures and updates. It was clear my cat was comfortable and well cared for, which means so much to me. I really appreciate how thoughtful and reliable she was. I’ve already booked her again and wouldn’t hesitate to recommend her to anyone!”
Katie M.
“This wonderful lady was very willing to help us out and she went above and beyond for our dog Emma. After a couple pouty moments emma finally settled in and had a blast playing with the other Dog I will rebook with her if we both have mutual dates. Please allow her to watch your pets”
Taylor M.
“Great experience with Taylor n company. Kept me well informed and sent plenty pics. Definitely would recommend Taylor for taking care of your pups.”
John S.
“I was a nervous wreck! John and his fiancée were wonderful hosts for my 2 large, spoiled dogs. The dogs had access to their home and a huge backyard. I got photos and updates, daily. The dogs came back happy and tired. Will definitely use them again!”
Alexis R.
“Alexis watched my dog Cassie while I was in town for a few days. She was communicative in the lead up and during the stay. She took great care of Cassie and I would definitely book with her again next time I'm in town.”
Rebecca N.
“Rebecca and her family provided a loving home for the weekend while we were away! Their two dogs were very gentle and sweet and my dogs loved playing with them. Her kids are also great. We look forward to booking again!”
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?
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, 112 sitters provided dog boarding in Winesap. 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, 87% of Winesap dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winesap have an average of 20 years of experience. Dog boarding sitters with repeat customers have an average of 8 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 Winesap.
Rover makes it easy to find Winesap 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 112 dog boarding sitters in Winesap on Rover, so you’re sure to find the perfect match for your dog! In Winesap, 100% of sitters offer daily exercise, 100% offer medication administration, and 80% 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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