Dog Boarding in Chestertown

“I can’t say enough about Gisel and her family that gave us a warm welcome the moment we connected. At our meet and greet, I knew she was the one to host our #furbaby Cody. Even her children were loving towards him. They are a wonderful family and far exceeded our expectations of caring for our Cody with pics and videos the whole seven days. Our neighbor uses her as well for their Yorkie and are very pleased with the care they’ve received. The bonus for us, she’s a stay at home mom and Cody was not left alone all day. She has small dogs as well and he was able to meet new friends. This was our first time leaving Cody without family and Gisel eased all of my anxiety because of her love for animals. We’ll be using her again soon.😊”

Lavonne T.

“My lab Ruby had a wonderful time with Jacob and Megan. She was super excited that she would be able to play with other dogs and lounge on their deck. She was exhausted when she came home. I definitely recommend Jacob and Megan as dog sitters and would take Ruby back again!”

Nancy B.

“We’re so grateful for the great care Katelyn took of Hank! And appreciate all the communication - receiving pictures, videos, and updates on how well it was going. It was our first time entrusting Hank to a dog sitter so I was nervous but it went perfectly!”

Laura G.

“I highly recomend Michele. She was always quick to respnd. She sent many pictures every day so I could see that my boy was enjoying his stay. She has a beautiful backyard that my boy enjoyed running around. The best part of my boys stay at Michele's house is that he made a bunch of new playmates cand canine fcompanions.”

Dean B.

“Carlie and her family could not have been more loving and attentive. Arlo probably wanted to live there forever. She was incredibly kind about a mistake I made on pick up time.”

Jennifer M.

“Paris took great care my Deacon and sent me updates of pictures that I adore She was very professional. I will definitely be using Mrs. Paris service again because I was very satisfied”

Jamie B.

“Danielle took great care of my dog while I was away! Sadie was happy and well cared for when I picked her up. Danielle was responsive and sent me regular updates so I knew Sadie was happy and safe. I highly recommend Danielle!!”

Kate F.

“Leaving our Mr G with Theresa was an wonderful experience. She was informative, personable and we knew our buddy was well taken care. She is a wonderful care giver and I would recommend her dog sitter services for anyone looking.”

Neil A.

“My frenchie had the BEST time with Lindsay and her puppy!!!! Lindsay sent me pics daily, and whenever I asked for one. My baby literally had so much fun at her house, I think he sulked for a few days after ? Lindsay will be our go to for boarding in the future.”

Dana L.

“Shuling always makes me feel so much better about leaving my needy dog, manny, when I go for vacation. He always comes back with a huge smile and has so much fun playing with her dog, Bear. Thank you so much, Shuling!!”

Lainey R.

“These folks are amazing. They were born to board pets - my boy Marvin had the best time! You will not regret leaving your precious pooch with them!”

Tom Z.

“Tango had a wonderful time, and was very happy with her stay with Dawn and her family. She fit right in as a member of their “pack” I was very pleased with the care she received, she had plenty of fun and stimulation too.”

Margaret C.

“Lucky had a great time with Max and Thomas. He enjoyed playing in the backyard and all the pets. Thank you and I'll definitely rebook again. I appreciate the prompt replies to my texts.”

Tricia O.

“⭐️⭐️⭐️⭐️⭐️ I don’t know how to explain this except: Jess is basically Dodger’s second family now. ⭐️⭐️⭐️⭐️⭐️ If you’re looking for the type of sitter who treats your dog like FAMILY…like actual family…Jess is the one. I honestly don’t think Dodger realized he was being “boarded.” He thought he was on vacation with his new cousins, new uncles, and his new favorite person on earth (Dan 😆). From the minute we dropped him off, Jess was so reassuring and kind. She sent constant updates, pictures, and little stories that made my heart feel so much better. And not just “here’s your dog existing” pictures…NO. We’re talking: *Dodger cuddling her husband like they’ve been best buds for 10 years *Dodger snuggled up with her youngest like they were watching Saturday morning cartoons *Dodger and Tanner acting like long-lost brothers reunited *Dodger eating, relaxing, wagging his tail like a helicopter blade *Dodger getting a whole spa bath after rolling in the yard mud 😭💀 He even chewed through a Kong, which honestly deserves its own award. I warned her he was a super chewer, but I don’t think ANYONE was ready for him to destroy the “indestructible” toy. She just laughed and sent pictures like, “Welp, he’s having the time of his life.” 😂 The whole time she made sure I felt comfortable…even when my baby stole my phone and I panicked thinking I missed messages 😅 She was patient, flexible, and genuinely cared about him AND about us. Dodger came home happy, clean, tired, and FULL of love. His tail literally didn’t stop wagging the entire stay. And I’m pretty sure he thinks Jess’s house is his second home now…which I’m honestly fine with, because I know he’s safe and adored there. Jess and her whole family are wonderful, warm people. They treated Dodger like he belonged with them, and that’s all a dog mom could ever want. We will definitely be booking again (unless Dan steals him permanently 😂). Thank you, Jess, for loving our boy so well. He misses you all already! ❤️🐾 P.s thank you for being so accommodating and helpful with his bath, I loved getting to pick him up early and snuggle him with us the moment he came home🥹💕”

Deidre L.

“Ran into a need of a last minute sitter for a night, had quick response time of being able to watch my dog. When I picked her up the next morning she was a happy and sleepy girl!”

Samantha G.

“Barb was fantastic! We chose her because of her experience with dogs of all ages, especially older pups. Although our pup was a bit nervous, she seemed to settle in well and made herself at home. Really appreciated the updates and pics to let us know all was good.”

Meg M.

“Sherman loved his time with Jill and Chad and family!!! We could tell that he got so much attention and affection. Sherman can't wait for his summer vacation in July!”

Patricia Y.

“Marliez took amazing care of Ozzie. He walked with her Husky Wolf several times a day receiving plenty of needed exercise. Oz was received as part of her family. I could tell from the photos he was really enjoying his stay and looking forward to go back. Marliez paid attention to the nuance of my dog's antics to adjust to him. She is a wonderful sitter”

Raymond L.

“Fantastic sitter who went above and beyond in every way. Rich was careful and attentive, giving our dog everything she needed. Would highly recommend.”

Matt L.

“I had an excellent experience with Pat and Bee. They truly cared for my dog as if it were their own, which gave me so much peace of mind while I was away. I especially appreciated the daily photo updates and how quickly they responded to any questions I had about my dog’s day. Their large backyard was a huge plus—my dog had plenty of space to play, explore, and have fun. It’s clear they provide a safe, loving, and engaging environment for pets. I will definitely be booking with them again and highly recommend them to anyone looking for a trustworthy and attentive sitter!”

Khadijah C.