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

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


“I can never say enough about about her wonderful services. My dog is older and has some special abilities that need to be tended to. She has dogs herself that are gentle and playful that supplies my dog with a plenty of playmates. She also never kenneled my dog which was a big worry for me. Time and time again I would never choose anyone else to take care of my sweet boy.”



“Laura and her family were great. She sent daily updates, responded quickly, and was able to work with our schedule. Brady looked happy and well cared for. Would definitely board with her again!”


“Another amazing stay with Cassie! Sully had a blast with his buddies and has not moved since he got home. He's exhausted which is wonderful. There are not enough starts available to rate how fantastic Cassie is with all the dogs in her care. It truly is Sully's home away from home and I never, ever worry about how he's doing because he's in great hands with Cassie. Thank you, Cassie for another amazing stay. We are forever grateful to you for all you do for Sully while we're away.”


“Milo had a great time with Dahlia and Jalen! They sent us updates throughout the weekend and photos of him snuggling, taking walks outside, and playing with their pup, Kris, and his toys. Their fenced-in back yard and work-from-home lifestyle were added bonuses for our curious and social pup. When we picked him up, he was relaxed and happy. We’re so pleased to have found a dog sitter who is caring, attentive, trustworthy, and fun!”


“Exceptional experience! Despite our fragile itinerary, Cindy remained flexible. As soon our dog met Cindy, she immediately felt welcome and willingly followed Cindy. The pictures confirmed how safe and comfortable our dog felt with Cindy. Next trip, Cindy will be our first choice.”


“My gosh, Paula is a dream come true. She is being so caring with Jackson. She keeps him occupied and is making him a better dog. If (when) he does something that's not wanted she uses redirection and positive reinforcement to improve his behavior. Very pleased with the care she gives Jackson. And she kept me up to date during the stay.”


“If you are going out of town and need a family for your fur babies to hang out with Lucky B is awesome!!! We changed our drop off and pick up time due to family visits and arriving back a bit late. Lucky B. was super supportive and edited the times. While we were away plenty of photos were sent of our Riley running... snuggling... and having a great time. We received a report of how she did and treat bags for both Riley and our family. We will always check Lucky B's availability before we book with anyone else. Thank you so much for giving Riley a comfortable place to hang out for a week. I know that being in a home.is so much better for her than a boarding facility.”


“Stephanie had such wonderful communication and my cat was extremely safe and comfortable. Well recommended and will definitely use her services again. Thanks for the extra treats”


“Riley really enjoyed her stay with Kristen. She especially loved playing with Wally and she came home happy and tuckered out. Thank. you so much again!”


“They gave us updates and sent pictures that made us feel better about leaving Flex for the first time. We would recommend them and hope to use their services again. We can’t thank them enough.”


“This was our first-time using Miranda and she made us feel comfortable from the very start. We started with a pre-stay meet and greet to make sure our dogs got along, and everything went perfectly. Miranda did an awesome job with Draco from the time we dropped him off until the time we picked him up. She sent us many videos and pics and in all of them he looked super happy. It really seemed that he had acclimated and became a part of her family, and they treated him as such. He also really enjoyed playing with their son and their beautiful chocolate lab. We will definitely be using her again in the near future. Draco looked like he was having such a great time in all the pictures and videos, and we were worried that he wouldn't want to come back home to us LOL.”


“Laura is wonderful and very accommodating. She was understanding and flexible when my car wouldn't start and couldn't make it for pick up. She's very sweet and fun. Very responsible for Bailey and easy to talk to. I'll definitely use her again!”


“Amanda and Adam sent me pictures of our dog every day and an update on how she was doing. She is a not an easy going dog because she is nervous and has separation anxiety, but they were able to handle her and she liked them, their dogs and their kids. We will be using them again next time we travel!”


“Lori & her husband took phenomenal care of Sammy & Sylvie (again) while we were away for the week! I couldn’t have asked for better caregivers to make my fur babies feel loved & secure while we were out of town! Lori made a genuine effort to follow through on the pups’ daily routines & we received daily updates with pics & vids as well! I can’t thank Lori & her husband enough for taking such excellent care of my Sammy & Sylvie! We will definitely be seeing them again soon! 🥰”


“Alex is the best! Our dog was well cared for, had access to Alex’s backyard, and socialized with other well behaved rover pups staying at her house! She came back looking loved and well cared for! Alex sent us so many photos and we loved having updates throughout our dogs stay! Would recommend Alex to anyone!”


“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!”



“I can't say enough about our dog's first boarding experience with Helen. She made Finn - and us! - feel comfortable from the moment we met her. It's obvious how much she loves her animals and the ones she cares for. She sent regular pictures and updates, which we loved! And the Webcam's are an added bonus!! I never worried about Finn while he was in Helen's care, and he loved every minute of it. Finn will definitely be back for "Camp Helen!"”


“This was the longest time I've been away from my pup and Michelle did another amazing job. He always looks like he's having the best time with Milo and I appreciate all the updates and pictures they send! So happy to have found a great sitter for my boy!”


“Hali took very good care of our boy and was easy to communicate with! She sent pictures throughout the entire week so I always knew how he was doing. He also enjoyed playing with their friendly dog- Cooper! I would highly recommend her to anyone looking for a pet sitter!”

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.




DAMACIA J.Star Sitter

“I can never say enough about about her wonderful services. My dog is older and has some special abilities that need to be tended to. She has dogs herself that are gentle and playful that supplies my dog with a plenty of playmates. She also never kenneled my dog which was a big worry for me. Time and time again I would never choose anyone else to take care of my sweet boy.”




Laura B.
Star Sitter


“Laura and her family were great. She sent daily updates, responded quickly, and was able to work with our schedule. Brady looked happy and well cared for. Would definitely board with her again!”


Cassandre S.
Star Sitter


“Another amazing stay with Cassie! Sully had a blast with his buddies and has not moved since he got home. He's exhausted which is wonderful. There are not enough starts available to rate how fantastic Cassie is with all the dogs in her care. It truly is Sully's home away from home and I never, ever worry about how he's doing because he's in great hands with Cassie. Thank you, Cassie for another amazing stay. We are forever grateful to you for all you do for Sully while we're away.”


Dahlia & Jalen B.Star Sitter

“Milo had a great time with Dahlia and Jalen! They sent us updates throughout the weekend and photos of him snuggling, taking walks outside, and playing with their pup, Kris, and his toys. Their fenced-in back yard and work-from-home lifestyle were added bonuses for our curious and social pup. When we picked him up, he was relaxed and happy. We’re so pleased to have found a dog sitter who is caring, attentive, trustworthy, and fun!”


Cindy T.


“Exceptional experience! Despite our fragile itinerary, Cindy remained flexible. As soon our dog met Cindy, she immediately felt welcome and willingly followed Cindy. The pictures confirmed how safe and comfortable our dog felt with Cindy. Next trip, Cindy will be our first choice.”


Paula H.Star Sitter

“My gosh, Paula is a dream come true. She is being so caring with Jackson. She keeps him occupied and is making him a better dog. If (when) he does something that's not wanted she uses redirection and positive reinforcement to improve his behavior. Very pleased with the care she gives Jackson. And she kept me up to date during the stay.”


Lucky B.


“If you are going out of town and need a family for your fur babies to hang out with Lucky B is awesome!!! We changed our drop off and pick up time due to family visits and arriving back a bit late. Lucky B. was super supportive and edited the times. While we were away plenty of photos were sent of our Riley running... snuggling... and having a great time. We received a report of how she did and treat bags for both Riley and our family. We will always check Lucky B's availability before we book with anyone else. Thank you so much for giving Riley a comfortable place to hang out for a week. I know that being in a home.is so much better for her than a boarding facility.”


Stephanie B.Star Sitter

“Stephanie had such wonderful communication and my cat was extremely safe and comfortable. Well recommended and will definitely use her services again. Thanks for the extra treats”


Kristen & Christopher W.Star Sitter

“Riley really enjoyed her stay with Kristen. She especially loved playing with Wally and she came home happy and tuckered out. Thank. you so much again!”


Carina S.

“Carina is the best and took such great care of our dog for the weekend! Will definitely use again!”


Royal & Rhonda P.Star Sitter

“They gave us updates and sent pictures that made us feel better about leaving Flex for the first time. We would recommend them and hope to use their services again. We can’t thank them enough.”


Miranda C.Star Sitter

“This was our first-time using Miranda and she made us feel comfortable from the very start. We started with a pre-stay meet and greet to make sure our dogs got along, and everything went perfectly. Miranda did an awesome job with Draco from the time we dropped him off until the time we picked him up. She sent us many videos and pics and in all of them he looked super happy. It really seemed that he had acclimated and became a part of her family, and they treated him as such. He also really enjoyed playing with their son and their beautiful chocolate lab. We will definitely be using her again in the near future. Draco looked like he was having such a great time in all the pictures and videos, and we were worried that he wouldn't want to come back home to us LOL.”


Laura N.Star Sitter

“Laura is wonderful and very accommodating. She was understanding and flexible when my car wouldn't start and couldn't make it for pick up. She's very sweet and fun. Very responsible for Bailey and easy to talk to. I'll definitely use her again!”


Amanda & Adam B.Star Sitter

“Amanda and Adam sent me pictures of our dog every day and an update on how she was doing. She is a not an easy going dog because she is nervous and has separation anxiety, but they were able to handle her and she liked them, their dogs and their kids. We will be using them again next time we travel!”


Lori N.

“Lori & her husband took phenomenal care of Sammy & Sylvie (again) while we were away for the week! I couldn’t have asked for better caregivers to make my fur babies feel loved & secure while we were out of town! Lori made a genuine effort to follow through on the pups’ daily routines & we received daily updates with pics & vids as well! I can’t thank Lori & her husband enough for taking such excellent care of my Sammy & Sylvie! We will definitely be seeing them again soon! 🥰”


Alexandra O.Star Sitter

“Alex is the best! Our dog was well cared for, had access to Alex’s backyard, and socialized with other well behaved rover pups staying at her house! She came back looking loved and well cared for! Alex sent us so many photos and we loved having updates throughout our dogs stay! Would recommend Alex to anyone!”


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!”




Helen G.Star Sitter

“I can't say enough about our dog's first boarding experience with Helen. She made Finn - and us! - feel comfortable from the moment we met her. It's obvious how much she loves her animals and the ones she cares for. She sent regular pictures and updates, which we loved! And the Webcam's are an added bonus!! I never worried about Finn while he was in Helen's care, and he loved every minute of it. Finn will definitely be back for "Camp Helen!"”


Michelle T.Star Sitter

“This was the longest time I've been away from my pup and Michelle did another amazing job. He always looks like he's having the best time with Milo and I appreciate all the updates and pictures they send! So happy to have found a great sitter for my boy!”


Hali M.

“Hali took very good care of our boy and was easy to communicate with! She sent pictures throughout the entire week so I always knew how he was doing. He also enjoyed playing with their friendly dog- Cooper! I would highly recommend her to anyone looking for a pet sitter!”
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?
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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, 732 sitters provided dog boarding in Chestnut Hill. 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, 92% of Chestnut Hill dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chestnut Hill have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 11 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 Chestnut Hill.
Rover makes it easy to find Chestnut Hill 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 732 dog boarding sitters in Chestnut Hill on Rover, so you’re sure to find the perfect match for your dog! In Chestnut Hill, 97% of sitters offer daily exercise, 95% offer medication administration, and 91% 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.
