Dog Boarding in Winding Creek South, MD

“Renee and her husband were great sitters for our 18-month old, very anxious rescue dog. They were very accommodating - we needed to adjust dates and they were fine with that. Maggie had a great time with them - they gave her time to feel confident and comfortable before introducing her to the other dogs in their household. I received a picture and a happy update each day of Maggie's stay. They were comfortable administering Maggie's daily medicine.”

Sharon B.

“Our pup stayed with Emily for 8 nights while we were traveling out of town. I felt 100% confident that she was safe and loved in Emily’s professional care. We received updates by photo and message (even a video!) along the way. I am soo grateful that we found Emily on Rover -and would recommend her without hesitation!”

Theresa M.

“Jeannie and Robert were fantastic caretakers for our dog. They showed us a video of their home, so we could see where he would stay, and answered any and all questions. During our dog’s stay, they sent sweet photos and videos, just enough so we’d know he was doing ok and could enjoy our holiday vacation. They took care of another dog during that time, and they were very careful introducing the two and making sure they got along. Ours was happy to have a four-legged companions as well as his human caretakers to keep him from feeling lonely. They even sent our pup home with holiday gifts. He came home happy, clean and calm. We hope he gets to visit them again and highly recommend their services. Thanks Rover and Jeanie and Robert!”

Laura W.

“I always feel at ease when I leave Nelly with Emily. She really seems to care about dogs, and I can tell that Nelly is having a good time when I arrive.”

Carlotta J.

“Jaclyn has been phenomenal in every way! Her exceptional service and flexibility have been key for us, making scheduling stress-free and convenient. We completely trust her with our dog’s safety and well-being, which is such a relief when we’re away. Her professionalism and clear, consistent communication stand out, always keeping us updated and reassured. Jaclyn truly goes above and beyond, and we’re so grateful to have found her. Highly recommend her to anyone looking for a reliable and caring sitter!”

Jay C.

“Was extremely happy with the week Our pup developed some separation anxiety while we were gone Charlie went above and beyond to make sure Cai was comfortable including sleeping on the couch next to him so he wasnt alone or scared Constant communication and pictures daily Highly recommend was a great experience all the way around!!!”

Marc W.

“Our Springer Spaniel seemed to really enjoy hanging out at Jesse’s. The pictures of how he spent his days were a welcome addition for his parents!”

Edith H.

“Erika was an excellent caretaker for our senior dog while we were out of the country. She was communicative and attentive to his needs, and it was clear when we returned that he had been comfortable and well looked after.”

Jaylynn W.

“Sarah was amazing! Our dog felt completely at home with her and was loved and spoiled rotten. We received photos and updates throughout the stay which was greatly appreciated. Definitely be using her again!”

Jen W.

“Ruth took amazing care of my dog Lilly and I couldn’t be happier with the experience! From the start, she was professional, communicative, and incredibly attentive to Lilly’s needs. She provided regular updates (including adorable photos!), and treated my dog like part of the family. I came home to a happy, relaxed pup, which says everything. Thank you so much for your fantastic care! I will use you again for sure.”

Jen F.

“Amazing once again! I never have to worry about my dogs when we are out of town and leave them with Kelli. She loves them like they are her own.”

Heather S.

“Kelly was absolutely amazing ! She took care of Mamgo as though it was one of her own fur babies. Always sending updates and pics. You could tell she made him feel at home ! We will definitely be calling her again to watch over our sweet boy. Thanks Kelly !”

Maria S.

“Rose was wonderful with Baxter! He was one happy puppy playing with Nola and taking walks with Rose. He was giving kisses when he left. We have already booked our second visit with Rose! She is awesome and I strongly recommend her!”

Vicki K.

“Lejune & her husband Michael were extremely friendly & welcoming. I was updated on my Benny’s routine and happenings throughout his stay, along with pictures. As we were leaving, Benny stuck to Lejune & didn’t seem to want to leave! I can tell he was so loved & well taken care of during his overnight stay. Highly recommend & will definitely be using Lejune again!”

Brittany S.

“Kristine and her family were wonderful with our two dogs! They treated them like their own and our dogs seemed so happy and comfortable in their home, with their kids and their dog. I loved getting updates/pics of them and communication was great. we will definitely book again!”

Danielle G.

“This place is dog heaven!! We will absolutely hire Kayleigh again. She’s so good at taking care of animals. Look no further people, this is the one to hire!”

Dakota B.

“Donna and Scott are AMAZING. We needed a last minute sitter and they welcomed our pup with open arms. Our dog is very nervous and barked when he arrived, but Donna and Scott knew exactly what to do to make him feel comfortable and at home. They sent multiple pictures of our dog at their house, and I had no doubt he was in the best hands. Thank you again for your flexibility, patience, and love for our dog!”

Kelsey D.

“Tina is great with Alex. She responded to my message quickly. She sent photos of Alex to let me know how he is doing. I will use her service again when I am in the area.”

Grace X.

About: I grew up in a dog-loving home—there was never a time we didn’t have a furry friend in the family. Since my very first pet, I’ve enjoyed caring for animals. Now as an adult, I have two dogs and a cat of my own. One of my pups is a sweet senior who enjoys the slower pace of life, and the other is a high-energy guy I’ve raised since he was a puppy. We went through all the training together—lots of patience, consistency, and treats!—and now he’s a well-behaved, happy companion who keeps me on my toes. My cat is curious and full of personality, always finding new spots to nap and new ways to charm everyone. Fun Facts Just About Me: I moved to Hagerstown with my fiancé, 2 dogs and cat about 2 years ago. My fiancé and I are getting married in May 2026. I play adult softball and kickball. I love to be outside whether it's walking the dogs, attempting to garden or being on the water. Since I work from home, I’m lucky to spend lots of quality time with my pets throughout the day, and I’d love to extend that care and attention to your furry family members too. Whether it’s going for walks, sticking to a feeding routine, or just offering companionship, I’ll make sure your pet feels safe, loved, and right at home. When caring for pets, whether in my home or yours, safety and trust are my top priorities. In my home, I provide a calm, secure environment with a fully fenced yard that offers plenty of room for pets to run and play safely. We also have sidewalks throughout the neighborhood perfect for walks, a puppy play pen for supervised fun, and plenty of space to crate pets comfortably if needed. All areas are pet-proofed to prevent accidents, and I carefully manage food, toys, and any medications. When visiting a client’s home, I follow their routines closely to keep pets comfortable and stress-free. I make sure doors and gates are secure, hazardous items are out of reach, and I maintain open communication with owners about any special needs or behaviors. Building trust with pets and their families is important to me, so I take time to understand each pet’s unique personality and needs.

“I was very happy with the care my pup was provided. I received lots of photos during his stay and daily updates on him. I will most definitely bring him back for future dog sitting needs ?”

Carolyn K.