House Sitting in Winchester

“Katie was absolutely lovely, and the pets got on with her really well. She sent through updates and photos, and made sure we felt comfortable (all on a holiday, too!) -- thank you Katie!”

Austen W.

About: I love all kinds of nature and wildlife, but especially dogs, cats, and reptiles! I have experience handling many kinds of animals through my biology research, and I also trained my own puppy! I'm in the northwest corner of CT for the summer before I move out west to start my PhD in biology (did I mention I love animals?). I'd love to meet your pets while I'm around! I’m currently working part-time and have lots of flexibility to stop by for walks, especially during weekdays. My schedule is very easy to work around. I love being outside and would be happy to take your dog on walks or hikes in the area. I’m also happy to stop by and play with your pets or just give them some love!

“Theresa was great with my tiny puppy (14 weeks)! I came home to a very happy and calm pup who had clearly had a wonderful afternoon. Theresa is a real pro - I’m new to this, and she was extremely helpful explaining potty training and leash weights.”

Anna H.

“Jared stayed over night with our dog Moose. He was very communicative, sent constant picture updates and was also very flexible on timing. He made sure Moose was well taken care of. We will definitely use Jared for any future needs for Moose.”

Jamshed D.

About: I’ve been pet sitting for over three years. I’ve had various experiences with dogs and cats. As someone who has a dog of their own, I’ve been able to observe behaviors that’s helped when taking care of other dogs, to understand their needs and wants. I currently work remotely however, it doesn’t take time away when it comes to the fur babies! In fact, it allows me to be present and give them the much needed attention. I understand the environment the pets are settled in. I give daily updates to the home owner, making sure that any anxiety of leaving their pets behind is relieved. I bring my own food and care.

“We are so grateful to have found Kelly and Nabil! They are incredibly attentive, caring, and down to earth. We are already planning another trip knowing our dog will have such amazing care.”

Joey W.

“Carol is simply the best sitter I’ve ever used! She is so caring, kind and accommodating and provides sweet updates for my girl. I know that Harper is in excellent hands with her and will be so well taken care of. She loves the dogs like her own and will be SO missed after her move!!! Thank you 🥰”

Caroline E.

“Annie was awesome!! She took great care of our golden, he had his own vacation while we were gone. Annie kept us up to date and sent some great pictures. She is a natural and our dog absolutely loves her!”

Sherri C.

“Stacey was wonderful! She was so easy to communicate with ahead of watching our dog and was also super self sufficient around our house. There was a bad storm when she was scheduled to watch our dog and we live in a pretty remote area and she had zero complaints. She was fantastic all around!”

Emily M.

“Jesse is THE BEST. After requesting the booking, he came out to meet us and our two boys, taking his own personal time to make sure it was a good fit. During his stay, he kept us informed with pictures and notes on the pups. He left our house just as he found it and, most important, we came home to 2 happy, sleepy dogs, tired after a vacation of their own! Jesse is reliable and incredibly knowledgeable and hardworking. Can’t wait to have him back!”

Judith C P.

About: When I was 10 I joined a dog training program through my school, that’s where my training experience began. I provide a premium, low-volume dog care experience for owners who want their dog to have more one-on-one attention in a calm home environment. Your dog won’t be just one of many in a crowded space. I keep my care more personal so each dog gets plenty of attention, supervision, and outdoor time. I have a big yard for dogs to enjoy, but my indoor space is smaller, so I am very intentional about keeping the number of dogs low. That means I can focus on your dog’s comfort, safety, and overall experience much more closely. This is a great fit for dogs who do better with a quieter setting and for owners who value quality of care over high-volume boarding or daycare. I generally only take one to a few dogs at a time unless they are from the same household. I have a lot of experience with senior dogs. I took care of my childhood dog for 17 years of her long, beautiful life. I have experience working with small senior dogs specifically and I know all the little things that they appreciate. I also have experience with large dogs and can handle very big strong dogs. I also love hiking with dogs so if you have an energetic dog you need to burn off energy I am your guy. I have an acre yard with a fenced in front yard in a nice area. Any dog that boards with me would be treated like my own dog and let out very frequently to go to the bathroom and play outside. I would always remain home with your dog. Thank you for considering me and I hope to meet your pet soon! I’m currently a fully remote student so I am fully available. If I board a pet I will be with them full time to make sure they receive the care they deserve. I have a fenced in front yard, and a good amount of unfenced land in the back. My dog is very friendly and would keep your pet great company. He loves dogs and cats. I can easily crate your dog if needed, but would love to give your dog the pet experience and treat them like my own. I live in a nice are and have great access to the woods nearby as well.

About: Hello! I am a lifelong pet owner and animal lover with experience with everything from chickens and horses to cats and dogs. I have two canine family members myself: a medium-sized mix named Bonnie and a 10-pound Italian Greyhound/chihuahua named Rio. I know how hard it can be to find loving, reliable, and safe pet setters, which prompted me to open up my own home. My dogs love meeting new friends to play with. They get along well with others (though we always require a meet-and-greet before a sit) and are friendly with cats as well. My work-from-home career and spacious property allows me the flexibility to fully care for your pet without any interruptions such as commutes or 9-5 work hours. I am fortunate to enjoy a fully remote, flexible career, which means I am always present for your canine or feline family members. I can accommodate short or long-term stays, and am home throughout the day to maintain your pet's schedule, so they feel completely at home. I think it's important to a pet's sense of wellbeing to be able to keep to their usual schedule as best as possible while in my care. I live on five acres in a log home in a beautiful hilltown in Western Massachusetts, and have a fully fenced yard. I love taking my own pup on daily walks on our property or on nearby dirt roads, so if you have an active dog who needs exercise, I'm your person! If a less active lifestyle is better for your dog, I can fully accommodate that as well. Pets are allowed on my furniture and can make themselves cozy by my wood stove in winter or on my sunny deck in summer. I am familiar with using crates (if desired, but not required) and have a large finished basement perfect for playtime in the winter months.

“Elizabeth did a great job watching our two labs (one is a puppy!) at our home. She was very easy going and easy to work with. When we got home the dogs were happy and quite tired! I would definitely use Elizabeth again!”

Robyn M.

“Katherine did a great job with our Toby! He's a little shy around other people but he warmed up to her fast! We will definitely be asking her to watch Toby again!!”

Izabel R.

About: Animals have always been a big part of my life. I have experience working at a dog daycare and providing pet-sitting services for friends, family, and clients. I am comfortable caring for dogs of all sizes and personalities, including feeding, walking, playtime, and following specific care instructions. I am dependable, attentive, and committed to making sure every dog feels safe, comfortable, and loved while their owner is away. My goal is to provide peace of mind and quality care for both pets and their families. 🐾 Pet care fits naturally into my daily routine because caring for animals is something I genuinely enjoy. I have a flexible schedule and make it a priority to provide reliable, consistent care. Whether your pet needs walks, feeding, playtime, drop-in visits, or overnight care, I will make sure they receive the attention, exercise, and companionship they need Your pet’s safety and comfort are my top priorities. I carefully follow all care instructions, including feeding schedules, medications, exercise routines, and any special needs. I take the time to build trust with each pet and ensure they feel comfortable while you’re away. I will treat your home with respect and provide regular updates so you can have peace of mind knowing your pet is in caring and responsible hands. 🐾

About: I’ve taken care of dogs on and off for years and I’ve had a couple of my own. Would be happy to host your pet for a day or a few days, whatever your need is. I am fully retired at this time and will have plenty of time to play with and care for your pet. I am available weekdays and nights as well as some weekends. I am also available to watch them at your house as well if you’d prefer. I am happy to follow your feeding schedule and to take your pet for a daily walk. There are no young children or anyone else living in the house except me.

“Angela took great care of our three dogs while we were away for 10 days. They were all comfortable and relaxed with her. She’s gentle and patient and she even taught our littlest wild one some better manners. She sent regular updates and photos. We highly recommend her!”

Carrie & Rico A.

About: I’ve always been comfortable with dogs of all types. I grew up with dogs and have spent my whole life around animals, so caring for them feels natural to me. I’m calm, confident, and make sure to adjust to each dog’s individual needs so they feel safe, understood, and well cared for. I work full‑time during the day, but I’m available in the early mornings and evenings to take care of your pet. That gives me plenty of time for feeding, walks, playtime, or whatever they need before and after work. Mondays are my completely open day, so I’m available all day then for longer visits or extra care. My goal is to ensure your pet feels genuinely cared for. I pay close attention to their routine and what they need, and I make sure they stay comfortable, happy, and relaxed the whole time they’re with me.

About: I absolutely love dogs all shapes and sizes, when you book with me your dog will be in a safe and loving environment with me. it’s important to me that any dog i’m with at the time will have a fun and enriching environment with me and the time we’re spending together. I have experience training puppies and pet sitting puppies. I’ve done extended petting sitting stays and have done petting sitting with multiple animals, i’ve done week long stays with 6+ animals, so I can handle a big crew if you have it. I have experience with farm animals and horses as well if that’s ever needed as well! I currently am not working and would love to add some furry friends to my day! I am quite flexible with my timing right now and offer free meet and greets for the safety and benefits of all of us. If you use me for pet sitting you can expect your dog to be fully safe! I will follow your directions and expectations to the tea because I know what it’s like to have to leave your dog with someone and not wanting to have to worry about your loved one

About: What sets me apart is my hands-on experience and genuine love for dogs of all ages. I worked at a dog kennel for two years, where I cared for dogs with all kinds of temperaments, ages, and needs. I’m experienced with senior dog care and I’m comfortable with puppies too—whether it’s crate training, potty breaks, or just keeping up with their energy! Your pet’s comfort and safety are always my top priority. Pet care fits easily into my weekly routine since I have a pretty open and flexible schedule. I’m most available Tuesday through Friday between 11:30 AM and 4:30 PM, which works great for midday walks or drop ins. That said, I’m always happy to discuss and make arrangements that work best for you and your pet! Whether I’m caring for pets in my home or yours, their safety and comfort always come first. I take the time to understand each pet’s routine, needs, and personality to make sure they feel secure and loved. I keep a clean, pet-friendly environment and follow any instructions you provide whether that’s feeding schedules or favorite toys. I also provide regular updates so you can feel confident and at ease while you're away.