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

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

“Walter and his family were great hosts and caretakers for our dog. They made us feel super comfortable by sending updates and pictures while we were away. We have already asked them to take care of our dog again because of the wonderful care they provided!”


“When I'm looking for someone to care for my dogs, I want to make sure the individual has a place where there's plenty of space for them to exercise and that they're able to give my pups plenty of attention. Alexsys has all above the above. It was a lengthy stay for my dogs so I was a little nervous but she sent me pictures and updates throughout the entire stay. I'd definitely recommend her to other individuals on here and I will definitely be coming back as well.”


“Joshua and Kristen are always awesome. They take such good care of my dog as if she were one of theirs. I love the continual photos and updates they provide. I always feel so good/comfortable when they watch Lulu!!”



“She provided pictures and updates on him very professional and even showed me to get him out of trying to be a dominant male he still needs work but very pleased with what she did for him”


“Shaghayegh is truly the best dog sitter in Winchester! My dog, Toby, loves her and I always feel comfortable leaving him in her care. She gives daily updates with photos to let you know how your pup is doing. I really appreciate the great care she gives my dog every time he’s with her. 😊”



“Excellent as always we so appreciate how Tamara takes great care of Kai. He’s always so excited to stay with her. It makes it easier for us when we go out of town highly recommend.”


“Gabby was very responsive, caring, and flexible. She was engaged with the dogs during their stay and patient with our shy girl. She's also willing to take on this extra responsibilty during a busy holiday season. She is the best!”


“Lori was amazing and the pup was well taken care of, it was great knowing our pup was in good hands, we got updates through out the weekend, would recommend Lori to EVERYONE! :)”


“I cannot thank Michelle and her family enough for watching Bella multiple times! Michelle is great with sending pictures, and keeping me updated as to how she is doing, Of course Bella loves to cuddle with the entire family as well. I would give more than 5 stars if I could!”


“Haejin and Herscel were amazing with my elderly dog and made me feel so much more comfortable while being away from him. The provided detailed updates and you can tell they really care. Highly recommend!”


“Bella is an amazing Pet Sitter and dog groomer! This is the first time anyone has ever kept my Pom so I was a little nervous. All those nerves were put to reset the moment we met and you assured me my puppy was in good hands. I appreciate all the messages and photos you sent. These are some of the best photos I have of my puppy! I will definitely book you again and recommend you to outer pet owners.”


“Barbara took amazing care of my anxious dog. She provided daily updates of how my dog was adjusting. Thankfully, my dog adjusted quickly and had a wonderful time playing with Dobby and the daycare dogs. I was only a little worried my dog wouldn't want to go home because Barbara took such great care of her.”


“Kalley is an amazing sitter. She took awesome pictures and updated me daily on how my baby was doing. Thank you so much Kalley. We’ll be booking with again soon!”


“Linda was the sweetest! This was our first time using any kind of pet sitting services for our sweet Missy. The decision to leave Missy with a sitter was last minute, but I’m so grateful for Linda because she was extremely accommodating and amazing with Missy. Linda went above and beyond, sent pictures, and even a video as Missy adjusted to being around other campers. I will 100% leave Missy with Linda again in the future. Thank you so much Linda!! You are truly amazing and one of a kind!”


“Lots of TLC and a safe environment are top priorities when we select a dog sitter for our golden doodle. Sarah and her family all gave so much care and kindness to our pup. Frequent walks on her quiet street and a daily trip to the dog park provided exercise and fun stimulation. Sarah communicates promptly and thoroughly. She truly cares about my dog’s safety and wellbeing. We have booked a 2 week stay with Sarah this summer. We are very comfortable doing this knowing our dog is in such good hands.”



“Amazing!! My dogs ran around and she was able to give them their own fenced in area!! Will be coming back next time we need a sitter my dogs came back happy and tired!”


“Such wonderful animal lovers! I received nightly photos of our dog having the best time on their property. Would recommend them to everyone and will use them again.”


“We left our dog with Jessica for the weekend. She took great care of her & updated us with pics & videos . We will be booking with her again & highly recommend her !”


“This is my second time using Jaclyn and I was just as pleased this time around. Jaclyn takes care of your fur babies like they’re her own and truly goes the extra mile.”

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.


Walter G.
Star Sitter


“Walter and his family were great hosts and caretakers for our dog. They made us feel super comfortable by sending updates and pictures while we were away. We have already asked them to take care of our dog again because of the wonderful care they provided!”


Alexsys T.Star Sitter

“When I'm looking for someone to care for my dogs, I want to make sure the individual has a place where there's plenty of space for them to exercise and that they're able to give my pups plenty of attention. Alexsys has all above the above. It was a lengthy stay for my dogs so I was a little nervous but she sent me pictures and updates throughout the entire stay. I'd definitely recommend her to other individuals on here and I will definitely be coming back as well.”


Joshua & Kristen B.Star Sitter

“Joshua and Kristen are always awesome. They take such good care of my dog as if she were one of theirs. I love the continual photos and updates they provide. I always feel so good/comfortable when they watch Lulu!!”




Katherine B.Star Sitter

“She provided pictures and updates on him very professional and even showed me to get him out of trying to be a dominant male he still needs work but very pleased with what she did for him”


Shaghayegh H.
Star Sitter


“Shaghayegh is truly the best dog sitter in Winchester! My dog, Toby, loves her and I always feel comfortable leaving him in her care. She gives daily updates with photos to let you know how your pup is doing. I really appreciate the great care she gives my dog every time he’s with her. 😊”




Tamara G.

“Excellent as always we so appreciate how Tamara takes great care of Kai. He’s always so excited to stay with her. It makes it easier for us when we go out of town highly recommend.”


Gabby T.Star Sitter

“Gabby was very responsive, caring, and flexible. She was engaged with the dogs during their stay and patient with our shy girl. She's also willing to take on this extra responsibilty during a busy holiday season. She is the best!”


Lori V.Star Sitter

“Lori was amazing and the pup was well taken care of, it was great knowing our pup was in good hands, we got updates through out the weekend, would recommend Lori to EVERYONE! :)”


Michelle M.

“I cannot thank Michelle and her family enough for watching Bella multiple times! Michelle is great with sending pictures, and keeping me updated as to how she is doing, Of course Bella loves to cuddle with the entire family as well. I would give more than 5 stars if I could!”


Haejin & Herscel L.

“Haejin and Herscel were amazing with my elderly dog and made me feel so much more comfortable while being away from him. The provided detailed updates and you can tell they really care. Highly recommend!”


Yzabella V.

“Bella is an amazing Pet Sitter and dog groomer! This is the first time anyone has ever kept my Pom so I was a little nervous. All those nerves were put to reset the moment we met and you assured me my puppy was in good hands. I appreciate all the messages and photos you sent. These are some of the best photos I have of my puppy! I will definitely book you again and recommend you to outer pet owners.”


Barbara D.
Star Sitter


“Barbara took amazing care of my anxious dog. She provided daily updates of how my dog was adjusting. Thankfully, my dog adjusted quickly and had a wonderful time playing with Dobby and the daycare dogs. I was only a little worried my dog wouldn't want to go home because Barbara took such great care of her.”


Kalley B.Star Sitter

“Kalley is an amazing sitter. She took awesome pictures and updated me daily on how my baby was doing. Thank you so much Kalley. We’ll be booking with again soon!”


Linda E.
Star Sitter


“Linda was the sweetest! This was our first time using any kind of pet sitting services for our sweet Missy. The decision to leave Missy with a sitter was last minute, but I’m so grateful for Linda because she was extremely accommodating and amazing with Missy. Linda went above and beyond, sent pictures, and even a video as Missy adjusted to being around other campers. I will 100% leave Missy with Linda again in the future. Thank you so much Linda!! You are truly amazing and one of a kind!”


Sarah J.Star Sitter

“Lots of TLC and a safe environment are top priorities when we select a dog sitter for our golden doodle. Sarah and her family all gave so much care and kindness to our pup. Frequent walks on her quiet street and a daily trip to the dog park provided exercise and fun stimulation. Sarah communicates promptly and thoroughly. She truly cares about my dog’s safety and wellbeing. We have booked a 2 week stay with Sarah this summer. We are very comfortable doing this knowing our dog is in such good hands.”




Kristen K.Star Sitter

“Amazing!! My dogs ran around and she was able to give them their own fenced in area!! Will be coming back next time we need a sitter my dogs came back happy and tired!”


Briana J.

“Brianna was very attentive communicating with us and gave Apollo all the attention he loves. I will be using her services again :)”


Joel & Janelle E.Star Sitter

“Such wonderful animal lovers! I received nightly photos of our dog having the best time on their property. Would recommend them to everyone and will use them again.”


Jessica I.Star Sitter

“We left our dog with Jessica for the weekend. She took great care of her & updated us with pics & videos . We will be booking with her again & highly recommend her !”


Jaclyn S.
Star Sitter


“This is my second time using Jaclyn and I was just as pleased this time around. Jaclyn takes care of your fur babies like they’re her own and truly goes the extra mile.”
Popular requests near you
Select a filter and find qualifying Pyletown 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!
The median cost per night for dog boarding in Pyletown is $45
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 Pyletown average 14 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 235 sitters provided dog boarding in Pyletown. 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, 91% of Pyletown dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Pyletown have an average of 21 years of experience. Dog boarding sitters with repeat customers have an average of 14 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 Pyletown.
Rover makes it easy to find Pyletown 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 235 dog boarding sitters in Pyletown on Rover, so you’re sure to find the perfect match for your dog! In Pyletown, 94% of sitters offer daily exercise, 97% offer medication administration, and 94% 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.
