Dog Boarding in Winterberry, MD
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Top rated Winterberry dog boarders
“We are so grateful for the amazing care that Heather gave to our 1 year old golden (Cobain) over Easter break!! He really enjoyed his stay with her, the walks to the pond and the creek, playing with her daughter and their farm dog, Charles! We loved getting lots of updates and pictures ❤️ We will definitely be booking with Heather again!”
“We had the best experience with Rodney. He was very patient with Emma. She definitely warmed up to him. Unfortunately had to be late for pick up d/t airport delays - was not a problem. We would definitely use Rodney's help again.”
“Lonnie watched our border collie Gruffy while we went on a week vacation. Gruffy had a wonderful time with Lonnie and I am pretty sure he was on vacation too! Lonnie really did make Gruffy part of his pack that week and took the time to send us pictures. The pictures were great! I know Gruffy had a fabulous experience and we highly recommend Lonnie to anyone who has a fur baby.”
“This was my very 1st time being away from my fur baby & Carla made the process smooth. Very caring & kept me updated. The pictures helped a lot as well. Thank you so much again. This overall experience was a 10/10.”
“Evangelina has been wonderful with my puppy! I can tell it was important to her to truly care and tend to my pup’s needs! I also love that she sent pictures throughout. 10/10. Highly recommend!”
“Audrey was a great dog sitter. Her communication was awesome. She kept me informed throughout the day with messages and pictures. She also worked with me when I a few hiccups while out of town. I will book again.”
“Kristin was amazing! She was able to accommodate us on such short notice. She responded quickly and sent us updates daily (twice a day) on Kaijus well being. She would send us pictures of our pup which we really loved and appreciated as we were really nervous about leaving our puppy with someone we didn’t really know but she made us feel so comfortable. I would absolutely recommend her, will definitely be boarding our pup with her again!”
“Bruno and his family are so friendly and he communicated so fast and always sent me updates everyday. He was very willing to meet my dog ahead of time and we were overall very happy with Bruno. Would reccomend him!!”
“Chris did an excellent job with my little Moon! She was so accommodating and responsive to all his needs and whims! Chris will be the first person I look for if I ever need a sitter for my dog again😊”
“I can’t thank Vatina enough for taking such great care of my dog, Santana, over Christmas break. It’s never easy leaving your furry friend behind during the holidays, but knowing Santana was in such loving and capable hands gave me complete peace of mind. Vatina went above and beyond to make sure Santana was happy and comfortable, keeping me updated with adorable pictures and letting me know how he was doing. It was clear that she genuinely cared for him, treating him as if he were her own. Santana came back to me relaxed, well-cared for, and probably a little spoiled with all the extra attention. I’m so grateful for Vatina’s kindness, reliability, and attention to detail. I would absolutely recommend her to anyone in need of a trustworthy and caring dog sitter!”
“Megan was amazing! She set up a meet and greet to make sure everyone was comfortable and from drop off to pick up was very communicative! I will definitely be using Megan again and would recommend her sweet family to anyone looking for a sitter.”
“Jim and Mary took excellent care of Milo as usual! He’s a very anxious dog but does very well in their care! They sent lots of pictures so I could see how he was doing. I didn’t worry about him at all while I was away!”
“Brian was very flexible with my last minute booking! We did a meet and greet beforehand to make sure Athena got along with the dog in residence, which went very well though Merlin ended up not being there during Athenas stay. Brian was very responsive when I checked on him and Athena everyday. And Athena was clearly well taken care of even with her 4 month old puppy energy! I highly recommend Brian as a Rover caretaker.”
“We couldn’t be happier with the care our puppy dog received from Jena! From the moment we dropped him off, we felt completely at ease. We received daily updates with videos and pictures, which were such a comforting touch and really showed how much fun he was having. It was clear he was being treated like one of the family. When he came home, he was happy, healthy—and completely exhausted from all the playtime and attention! We're so grateful to have found such a trustworthy and caring sitter. Highly recommend!”
“Lora is nothing short than amazing with dogs! We were so nervous about trying a new dog sitter, but you can tell she loves dogs. She treats every dog she has as one of her own. We never had to worry about our furry kids, and she updated us constantly. We loved the amount of updates. She was so flexible and worked with us on drop off and pick up. Definitely plan on using her again!”
“Asani is awesome. She took care of my Violette like she was her own fur baby. She sent pics and videos throughout the weekend and most importantly, my dog didn't seem anxious with her at all. Will definitely book with Asani again!”
“Jacob was the absolute best with Benji. Our regular sitter was out of town and on short notice, Jacob saved the weekend for us. Right away from drop-off I had a sense of calm and peace with Jacob, his pets, and his beautiful backyard. Jacob sent pictures while away that showed Benji fitting right in with his new friends. I'll gladly use Jacob's services again and he really helped put our mind at ease!”
“Erika was friendly adaptable and kind. Our dog had a very nice stay. Erika sent us a few pictures and sent us periodic updates. We were pleased with her service and hope to use her again.”
Loving dog boarding sitters in your neighborhood
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Heather D.Star Sitter
“We are so grateful for the amazing care that Heather gave to our 1 year old golden (Cobain) over Easter break!! He really enjoyed his stay with her, the walks to the pond and the creek, playing with her daughter and their farm dog, Charles! We loved getting lots of updates and pictures ❤️ We will definitely be booking with Heather again!”
Rodney & Marissa O.
Star Sitter
“We had the best experience with Rodney. He was very patient with Emma. She definitely warmed up to him. Unfortunately had to be late for pick up d/t airport delays - was not a problem. We would definitely use Rodney's help again.”
Lonnie P.Star Sitter
“Lonnie watched our border collie Gruffy while we went on a week vacation. Gruffy had a wonderful time with Lonnie and I am pretty sure he was on vacation too! Lonnie really did make Gruffy part of his pack that week and took the time to send us pictures. The pictures were great! I know Gruffy had a fabulous experience and we highly recommend Lonnie to anyone who has a fur baby.”
Carla H.Star Sitter
“This was my very 1st time being away from my fur baby & Carla made the process smooth. Very caring & kept me updated. The pictures helped a lot as well. Thank you so much again. This overall experience was a 10/10.”
Evangelina S.
“Evangelina has been wonderful with my puppy! I can tell it was important to her to truly care and tend to my pup’s needs! I also love that she sent pictures throughout. 10/10. Highly recommend!”
Audrey S.
“Audrey was a great dog sitter. Her communication was awesome. She kept me informed throughout the day with messages and pictures. She also worked with me when I a few hiccups while out of town. I will book again.”
Kristin R.
“Kristin was amazing! She was able to accommodate us on such short notice. She responded quickly and sent us updates daily (twice a day) on Kaijus well being. She would send us pictures of our pup which we really loved and appreciated as we were really nervous about leaving our puppy with someone we didn’t really know but she made us feel so comfortable. I would absolutely recommend her, will definitely be boarding our pup with her again!”
Bruno D.Star Sitter
“Bruno and his family are so friendly and he communicated so fast and always sent me updates everyday. He was very willing to meet my dog ahead of time and we were overall very happy with Bruno. Would reccomend him!!”
Mila B.Star Sitter
“Mila took wonderful care of our dog Izzy! Izzy seemed very relaxed and right at home in Mila’s care. We highly recommend Mila if you’re looking for a dog sitter!”
Chris C.Star Sitter
“Chris did an excellent job with my little Moon! She was so accommodating and responsive to all his needs and whims! Chris will be the first person I look for if I ever need a sitter for my dog again😊”
Vatina H.
“I can’t thank Vatina enough for taking such great care of my dog, Santana, over Christmas break. It’s never easy leaving your furry friend behind during the holidays, but knowing Santana was in such loving and capable hands gave me complete peace of mind. Vatina went above and beyond to make sure Santana was happy and comfortable, keeping me updated with adorable pictures and letting me know how he was doing. It was clear that she genuinely cared for him, treating him as if he were her own. Santana came back to me relaxed, well-cared for, and probably a little spoiled with all the extra attention. I’m so grateful for Vatina’s kindness, reliability, and attention to detail. I would absolutely recommend her to anyone in need of a trustworthy and caring dog sitter!”
Megan B.
“Megan was amazing! She set up a meet and greet to make sure everyone was comfortable and from drop off to pick up was very communicative! I will definitely be using Megan again and would recommend her sweet family to anyone looking for a sitter.”
James & Mary H.Star Sitter
“Jim and Mary took excellent care of Milo as usual! He’s a very anxious dog but does very well in their care! They sent lots of pictures so I could see how he was doing. I didn’t worry about him at all while I was away!”
Brian M.Star Sitter
“Brian was very flexible with my last minute booking! We did a meet and greet beforehand to make sure Athena got along with the dog in residence, which went very well though Merlin ended up not being there during Athenas stay. Brian was very responsive when I checked on him and Athena everyday. And Athena was clearly well taken care of even with her 4 month old puppy energy! I highly recommend Brian as a Rover caretaker.”
Hannah A.
“Hannah took such great care of our dog! Our dog can't go off leash, and Hannah did an awesome job of keeping her safe while getting her plenty of exercise and play!”
Jena B.
“We couldn’t be happier with the care our puppy dog received from Jena! From the moment we dropped him off, we felt completely at ease. We received daily updates with videos and pictures, which were such a comforting touch and really showed how much fun he was having. It was clear he was being treated like one of the family. When he came home, he was happy, healthy—and completely exhausted from all the playtime and attention! We're so grateful to have found such a trustworthy and caring sitter. Highly recommend!”
Lora M.Star Sitter
“Lora is nothing short than amazing with dogs! We were so nervous about trying a new dog sitter, but you can tell she loves dogs. She treats every dog she has as one of her own. We never had to worry about our furry kids, and she updated us constantly. We loved the amount of updates. She was so flexible and worked with us on drop off and pick up. Definitely plan on using her again!”
Asani L.
“Asani is awesome. She took care of my Violette like she was her own fur baby. She sent pics and videos throughout the weekend and most importantly, my dog didn't seem anxious with her at all. Will definitely book with Asani again!”
Jacob L.Star Sitter
“Jacob was the absolute best with Benji. Our regular sitter was out of town and on short notice, Jacob saved the weekend for us. Right away from drop-off I had a sense of calm and peace with Jacob, his pets, and his beautiful backyard. Jacob sent pictures while away that showed Benji fitting right in with his new friends. I'll gladly use Jacob's services again and he really helped put our mind at ease!”
Erika D.Star Sitter
“Erika was friendly adaptable and kind. Our dog had a very nice stay. Erika sent us a few pictures and sent us periodic updates. We were pleased with her service and hope to use her 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, 1,155 sitters provided dog boarding in Winterberry. 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, 90% of Winterberry dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winterberry 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 Winterberry.
Rover makes it easy to find Winterberry 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 1,155 dog boarding sitters in Winterberry on Rover, so you’re sure to find the perfect match for your dog! In Winterberry, 96% of sitters offer daily exercise, 98% offer medication administration, and 93% 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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