House Sitting in Chestertown

“Jaimi was amazing and our senior dog loved her! Communication was great and the house was spotless when we came home.”

Gail C.

About: Over 16 years training, walking and exercising high energy dogs. I have extensive experience with working dogs, special needs dogs and have certifications in dog obedience and other disciplines. I am licensed as a public school teacher and fully background checked. Contact me for the best care. Boarding and adventure daycare is my speciality. I have limited housesitting and drop in availability. Dog walking and exercising is my full-time job. I want to provide a concierge service that makes it easiest for you to take your time back and be well. Your wellness is key to your dog being well. My joy for this profession started when I couldn't find a trusted sitter and dog walker for my own animal. I decided to provide that service to others so they wouldn't have the same problem. I give love, attention and exercise to your family member as if they were my own. I am a licensed public school educator who is fully background checked with glowing references that can be provided and contacted.

About: I have always loved animals and I have my own as well. I take care of my senior pup along with caring for friends and families pets as well. Always a good time with extra love to give. Reliable and fun. I work five days a week at a marina however, I am always open at night and on my days off I am more than happy to care for your animals. To care for my own pet I take him out multiple times a day, I walk him, feed him, bathe him, and so much more but with other animals it varies, depending on the instructions given by the owner is what I will do along with extra love.

“Jessica was the best. From the moment we met her, we knew we made the right choice and could enjoy a worry-free getaway. With her lengthy experience with animals, her excellent communication, and her pleasant personality, she was all we could ask for in a sitter. Our pet and home were so well taken care of. When we returned, Oscar was happy (he loved her) and our home was every bit as clean as when we left. We definitely recommend Jessica.”

David K.

“Kaleigh did an excellent job taking care of my fur babies! She gave me daily updates and kept in contact with me throughout my entire trip. Highly recommend kaleigh to anyone looking for an in-home dog sitter!”

Donielle L.

About: I have three dogs at home myself and love caring for them. I’ve previously worked at a dog daycare for a couple years and learned dog body language administering some medications and giving baths. I can help with feeding, providing exercise, bathing, administering medication, and ensuring that your animal with be safe and comfortable. I currently work part time and have flexibility with my current job that allows me to help care for your pet!! I am very flexible with days and times I will be needed to care for your pet. I have a big back yard for your dog to get it’s daily exercise I have three other dogs in my home to keep yours company!!

“Brandy housesat our 5 month old pup while we were visiting Johnsburg for a wedding! She was super responsive and flexible! She met us the day before to get to know the pup, the requirements etc. She was dependable and on time! She was kind and it was easy to see that she loves animals! She sent us pictures every few hours and kept us updated! Great experience!”

Piyumika D.

About: I have had pets all of my life. I trained my own dog to be a therapy dog. I also training him to do several tricks. I understand positive reinforcement training. I love cats also. I am currently working a full-time job but I have time on the weekends and early mornings or evenings to care for your pet. I am close to retirement and looking to take on clients part-time until I can convert to full time. I have a private yard. I welcome you to come in inspect my home prior to boarding your pets here. I have safety gates to keep your pets safe on the main level of our home.

“Laura was amazing and so essential to helping us get Colt from our wedding venue to our air bnb! She sent us absolutely amazing photos of Colt and took such good care of him. We can’t thank her enough!!”

Taylor H.

“Karen is extremely kind and pleasant. It was hard to tell she was even here! She took great care of our dog, even giving him a bath! He was very happy with her. We would use Karen again!”

Peter D.

“My dogs absolutely adored Alissa! I think they were almost disappointed when we came home! The were happy and stress free and my house was tidy. I really do not think that you can ask for anything more.”

Michele W.

About: I love all animals, I do have experience with medication administration, or reactive types of dogs. I am experienced in senior care or helping in training puppies while I care for your pets I currently work per-diem, and attend school full time. I have weekends free and evenings and always free to pop in most times especially overnights. My pup sleeps with me, he is spoiled like my own child. All my animals are well cared for and happy. I am comfortable stopping in for checkups or walks or even overnight stays

“Brittney was a wonderful sitter for our fur baby, she took great care of her! She sent pictures and updates, left the house spotless - we were so pleased and wouldn’t hesitate to book her again!”

Melissa W.

About: Animals have been part of my life for as long as I can remember. As a kid, I cared for hamsters, fish, and even a little parakeet. At 19, I adopted Max, a sweet lab mix who became my constant travel companion for 11 wonderful years as we explored the East Coast together. I’ve raised all my dogs from puppyhood, giving me plenty of experience with training, socializing, and caring for them through every stage of life. Today, my family and I live on 220 beautiful acres in Chestertown with: Beauty – Aussie Heeler mix (5) Scooby – lovable mutt (2) Yakko & Dot – tuxedo cats (3) 70+ chickens with big personalities A lively 55-gallon aquarium with community fish and snails, which has taught me the importance of maintaining delicate habitats Living with so many animals — from dogs and cats to chickens and aquarium life — has taught me patience, adaptability, and the joy of connecting with creatures of all kinds. Whether it’s walking a high-energy dog, keeping a shy cat comfortable, or caring for fish and poultry, I treat every animal like they’re part of my family. I split my time between Chestertown and Glens Falls, which means I can offer flexible pet care in both areas. I’m available for drop-in visits in Glens Falls on the days I’m there, as well as home stays in either location. I’m currently recovering from a car accident and walk with a cane, so while I can’t take dogs on long walks, I can safely let them out into a fenced yard or supervise them on a lead. At this time, I’m not offering boarding services in my own home, but I do plan to in the future. For now, my focus is on providing reliable, in-home care and check-ins so your pets can stay comfortable in their familiar environment. Whether I’m caring for pets in my home or in yours, their safety and comfort always come first. In your home, I follow your routines closely — from feeding schedules to favorite playtime activities — so pets feel secure in their familiar space. I make sure doors and gates are secure, keep an eye on water and food bowls, and provide supervised outdoor time in fenced areas or on a lead. In my home (for future boarding services), pets will enjoy a calm, animal-friendly environment on our 220-acre property, safely separated from my own animals as needed. I have experience managing dogs, cats, poultry, and aquarium life, which means I’m attentive to different needs and personalities. As a volunteer firefighter here in Chestertown, safety and responsibility are part of my everyday life. I also believe trust is built through clear communication — you can expect regular updates, photos, and honest feedback while your pets are in my care.

“Very responsive and great with the dogs. Very flexible as our plans changed last minute. Would not hesitate to book her again if we come back to the area.”

Jessica M.

“Colleen was great! Very communicative, took excellent care of our old doggo, and was neat as a pin. No hesitation about asking her to come back.”

Nancy L.

About: I am a vet tech assistant, going for my vet tech degree. I have worked in veterinary clinics for over 2 yrs. I have experiences with animals from reptiles, to kittens/puppies, and horses. I plan to pet sit on my days off/up to the first night I have to go into work, which would be Wednesday afternoon around 3pm is the last time I am available for a drop in varying on location could be earlier or a tad later. I love animals very dearly as I have 5 of my own and work in the veterinary medicine industry to help as many as I can. I will make sure your pets are well taken care of. Whether that be a bath, given treats, taken for a walk, let them run in your backyard, car ride, or even just relaxing in the living room. I will treat them as if they were my own.

“Jen was fantastic. She provided great communication and treated our babies like they were her own! 10000% recommend and will book again!”

Joseph K.

About: Over the last 7 years I have worked for many veterinary hospitals, including general practice and emergency medicine. With an associates degree in veterinary science, I’m well rounded to meet the needs of your fur babies! Working with animals Is what I love to do. Do you have special medical needs for your pet? No problem! I am very experienced with all forms of medications. Working for two veterinary hospitals, medicating animals is a daily need to know skill! Have a high energy pup that loves the outdoors? Rest assure they will be tired after some fun play time outside! I am very active and would love to bring your pup for a walk around the block/trails/dog park or play ball in the backyard! Need someone to stop by while you’re gone? I’m a great comfort friend and would love to help pass the time with your pet while you’re out for the day! I'm also very accommodating to those pets that may have more specific requests (anxious, does not like other dogs, food aggression, behavioral concerns, etc) I want to make sure each pet has fun but is also safe! I’d be happy to stop by before and after work (7am-5pm). I am fully available on Friday, Saturday and Sunday's. Of course I can accommodate and work around schedules as well. Small fenced in back yard along with daily walks over 30 minutes. Just a short drive away from multiple trails / parks in the area!

“Michelle was so kind and personable. I loved that she came to the meet and greet for our housesitting with a pen and notepad! She was a pro at giving our husky his meds, the house was left clean, and she was easy to communicate with while we were gone. Thanks, Michelle!”

Chelsea B.