Dog Boarding in Winchester Estates

Our dog Oakley had a great stay with Lindsay and her dog coco. She was sure to send lots of pictures and updates! Her large yard was great for Oakley and coco to run and get out their energy. We will definitely be booking again!

Carlie and family are incredible! Every time we go on vacation, I feel such peace and relief knowing Indi is enjoying herself - on her own little vacation, too! We get daily photos and updates, and Carlie even went above and beyond and helped us when we accidentally ran out of food (we packed too lightly) and dropped Indi back off for us. I highly recommend using Carlie's pet sitting services - thank you again!!

Hester was wonderful. She provided a loving home and daily photos. I would definitely recommend her to friends and have our dog stay with her again.

Max had a wonderful time at Mady’s home. Her dog Bandit was great with Max. I did not have to worry about Max the whole weekend. Received photos and updates which was very nice. Definitely be using Mady and her services in the future. Thank you Mady.

Scully loved his stay with Candace! She even made the dogs a special dog-friendly Thanksgiving meal! She sent a bunch of cute pics and sent quick updates throughout his stay. Will definitely be calling her again.

Theresa is the best. I was anxious to leave my furbaby for an extended trip, but she helped me feel at ease. She is experienced, responsible, and caring. And she gave my boy the best of care, while providing me with frequent updates. Thank you so much, Theresa ❤ 🐾

Megan is the best!! She took such great care of our dog and even took her on fun field trips! She was consistently communicative and sent pictures that showed me how she was enjoying her time with other dogs! I will highly recommend Megan to all my friends, and I will be rebooking. Thank you so much! We will be back!!

Our Bailey had a wonderful time with Shelby! She was an awesome communicator and very flexible with different timings! Definitely would recommend anyone looking for a sitter in the Annapolis area

I cannot praise this lady enough!! I felt completely secure leaving my babies with her! She communicated greatly throughout their stay and shared details with me to keep me at ease. She's extremely understanding and patient with my rescue babies as they warmed up to her and the family. Oleander gained a girlfriend during his stay too ? We will definitely be back! ❤️

Paisley did great and seemed to settle right in with the family and other dogs. She got lots of exercise and 1:1 attention. She ate pretty well and loved all the attention. So appreciate efforts to get her to eat and all the fun photos. She’s one tired pup now napping on the back of the couch.

Kendall was a great host to our dog! It was our first time leaving him, and it was a comfort to know he had a doggy friend and a family to play with him.

We couldn’t have asked for a better experience boarding Finn! From the start, Ben was warm, friendly, and welcoming, and his wonderful home felt like a safe, comfortable place for Finn to stay. We never worried while we were away. Ben consistently reassured us that Finn was having a great time and being incredibly well cared for. That peace of mind meant so much to us. We especially loved how active he was with Finn, taking him on lots of walks and giving him plenty of attention. His communication was excellent too. He was thoughtful about asking clarifying questions and checking in about any concerns, which made it clear how much he cared about getting everything right for Finn. We also had to make some adjustments to our drop-off and pickup times, and he was always flexible, understanding, and easy to work with. He’s truly a great guy, and we’re so grateful for the care he gave Finn. We would absolutely board with him again and recommend him wholeheartedly!

I felt confident leaving Ellie with Jacob and Melissa. They updated me with at least one photo and text each day so that I knew Ellie was enjoying herself. I would not hesitate to reach out to Jacob and Melissa next time I need to leave town.

Diana was wonderful with my senior dog, Charlie. She sent me pictures daily, and in every one he was grinning ear to ear! She has a large backyard and he thoroughly enjoyed himself. I don’t have a yard, so he’s always on leash. I’m so glad I found Diana!

Richard and Amy is true Animal lover Bruno loves them! They too kind to Bruno! I highly recommend them!

Joann treated our dog Poppy like she was her own. She was patient, kind and sent lots of updates and pictures. Poppy had the best time making a new pup friend and I know a pup-playdate is on the cards! Thanks Joann. You’re amazing. ☺️

Alicia was fantastic with my dog Sable. She kept us updated the whole time with pictures and videos which put us completely at ease. I would definitely feel comfortable leaving Sable with her again!

We booked with Noor again, and everything went great! Our Frenchie was well taken care of and came home happy. We’re so glad to have found someone we can trust with our pup. We would definitely recommend this sitter and book again!