House Sitting in Winchester

“Omar took good care of our house and our elderly cat while we are were away! He sent updates every day and paid attention to our cat's preferences.”

Becky S.

“Pan had a fabulous time with James. James treated Pan with love and care as if he were his own pup. We received transparent and timely communication, he shared lots of great photos and even took Pan on some fun field trips during the week. Would absolutely book again!”

Beth R.

“Andrew was fantastic. He sat for Cooper at our place for 4 days and did a great job caring for our pup, administering meds, and taking care of the house. Thanks!”

Tom & Tony A.

“We couldn’t have asked for a better first-time experience with a house sitter! From start to finish, Natalie was incredibly communicative, thoughtful, and proactive. She kept us updated throughout our trip with sweet notes and photos which brought us so much peace of mind while we were away. She followed all of our care instructions to the letter and when we returned home, everything was spotless. It was clear Emmy was well cared for. We’re so grateful to have found someone so dependable and kind. Highly recommend without hesitation!”

Nathan C.

About: I've always loved animals - I grew up around them on a small farm, took a couple years of animal science schooling, and currently volunteer on the Canine Enrichment team at a local shelter. Throughout these experiences, I've helped care for all kinds of animals with all types of needs. I'm no stranger to administering medications, helping dogs settle down, and knowing when a puppy "needs to go." While my life used to be an abundance of animals, now I just live with my sweet little kitty, Chef Mac. So, don't hesitate to reach out - I have plenty of space in my home and my heart for your pet! 𝑬𝒙𝒑𝒆𝒓𝒊𝒆𝒏𝒄𝒆 𝑪𝒂𝒓𝒊𝒏𝒈 𝑭𝒐𝒓: → 🐶🐱 The Usual - Dogs, Cats → 🐹🐁🐰 Lil Fuzzy Guys - Guinea Pigs, Hamsters, Rats, Ferrets, Chinchillas, Rabbits → 🐴🐔🐐 Barnyard Animals - Horses, Chickens, Goats → 🦎🐍 Scaly Friends - Bearded Dragons, Geckos, Snakes By the way, I love taking pictures and writing as a hobby. So, you'll be getting a lot of informative, photo-rich updates! 𝑭𝒓𝒆𝒒𝒖𝒆𝒏𝒕𝒍𝒚 𝑨𝒔𝒌𝒆𝒅 𝑸𝒖𝒆𝒔𝒕𝒊𝒐𝒏𝒔 "𝙸'𝚖 𝚘𝚞𝚝 𝚘𝚏 𝚛𝚊𝚗𝚐𝚎!" Send the request anyway! I tell Rover I'm willing to drive 15 minutes. We all live in Boston, right? So we know 15 minutes is kind of a vibe. If you're in the Boston Metro or North Shore area, we can probably make it work. "𝙸 𝚍𝚘𝚗'𝚝 𝚑𝚊𝚟𝚎 𝚊 𝚌𝚊𝚛!" I do! Just let me know and I can likely do pickup and drop-off. The number I put in my profile is a general estimate. I'll look at how much gas it will take to reach you, plus time, then I'll send you a quote. It'll probably be cheaper than ridesharing! 𝑺𝒑𝒆𝒄𝒊𝒂𝒍 𝑸𝒖𝒂𝒍𝒊𝒇𝒊𝒄𝒂𝒕𝒊𝒐𝒏𝒔 I am in the process of becoming Fear Free Certified and just enrolled in dog training classes. With your permission, I'd love to practice what I'm learning! I work freelance from home - so I have tons of flexibility to work around your pet's schedule (or, your hectic schedule!). Just a few exceptions: -> I volunteer once a week at the animal shelter on Mondays from 12 to 2. This is the only hard-and-fast time that I need to be out of the home. -> I do run a morning route with other animals. This means your pet will be alone for between one to four hours per day. Otherwise, there is almost always someone in the house. -> Sundays and Mondays are marked as unavailable for default on my calendar, but that's just because I can't help during midday. I have evenings available, though! Current special availability below: 𝚂𝚞𝚗𝚍𝚊𝚢𝚜 - 𝙰𝚟𝚊𝚒𝚕𝚊𝚋𝚕𝚎 𝚊𝚏𝚝𝚎𝚛 𝟼𝚙𝚖 𝙼𝚘𝚗𝚍𝚊𝚢𝚜 - 𝙰𝚟𝚊𝚒𝚕𝚊𝚋𝚕𝚎 𝚊𝚏𝚝𝚎𝚛 𝟹𝚙𝚖 - Before the appointment, we will align on expectations and your pet's daily needs. This will help us maintain a consistent routine and minimize stress to your pet. If any items seem challenging to fulfill, I'll proactively inform you of that. - If your pet will be visiting my home, they must tolerate cats. All boarding appointments will have a free Meet and Greet so we can screen for prey drive to ensure the safety of both animals. - If you're booking a boarding appointment for one dog, I might accept a boarding appointment for a second dog from a different family that is a similar size. If you'd like exclusive access to the house, please say so! - If you're booking for a cat, we will not book a new dog at the time that you reserve without your express permission. They will only stay with other cats and small animals. - While my yard is technically fenced, your dog will always be leashed and taken on walks for their safety.

“Tanya is outstanding. One of our dogs is very afraid of new people, but she warmed up to Tanya very quickly - much more quickly than I expected. Tanya was great with the dogs, respectful our of home, and highly communicative. She is a great dog sitter/walker and we would definitely hire her again.”

Travis H.

“Sasha was responsible, communicative and enthusiastic, and Rosie and I liked her right away! I would give Sasha the highest of recommendations, and hope to have her take care of Rosie again.”

Susan B.

About: I've always loved taking care of dogs! I had my first when I was 9, a beagle. Throughout the years I've done various dog-walking and dog/cat sitting for friends and family, and now I miss seeing all the dogs as I live away from them and they have passed :'( On multiple occasions, I took care of two loving but rambunctious pit bulls for weekends and extended periods of time while my friend was away. Gave them medicines, lots of attention, and invigorating walks. I took care of the house while they were away and sometimes stayed overnight. I have experience with dogs that need to be on a tight leash in certain scenarios, and experience allowing them to just have fun in safe spaces. With well-behaved dogs, I've gone on runs in the forest and been able to have them off-leash. I love having a buddy! I care a lot about maintaining the boundaries and rules around how you have trained your pet and keeping their routines. I manage an office nearby Monday thru Thursday, flexible Fridays. The morning walks are reliable and I can message you specifics and sort your dog’s and my schedule around it :) Most days, the afternoon walk can be configured into the schedule. We have a larger yard and no pets living in the house. My sisters nearby both have friendly dogs if yours would like some pals. Some days are busier or have a tighter walk schedule for me, but usually just 2 weekdays, which is why this works for me! I love taking dogs to different adventures like the Fells or games in my backyard, or just hanging out and cuddling :)

About: I got my Labrador retriever when I was 12, and I’ve loved dogs ever since. I will go out of my way to be around dogs - they really are a human’s best friend and such a life-changing companion — being around them has always felt natural and meaningful to me. I work fully remote, so I’m home a lot and have a flexible schedule. That makes it easy for me to give dogs plenty of attention, walks, and care throughout the day. I’m available for dog sitting any day of the week, and usually on weekends too unless noted otherwise. Your dog’s safety and comfort are really important to me. Since our apartment doesn’t allow pets, I’m always happy to come to your place so your dog can stay in their own familiar space and feel comfortable and relaxed.

“Nicole was excellent on her services. She stayed in our apartment for a house visit and she was super respectful of the place. She was very effective in communication and I was never wondering what our dog was up to, since Nicole planned out several activities and outings. I’m 100% hoping to re-book her for any future needs.”

Manuel G.

“Grace did a great job house sitting our elderly dog while we were away. She kept the house clean and our old Boston terrier was so well cared for I think he was sad to see her go. I’d recommend Grace to anyone that needs house sitting / dog sitting services.”

Devin B.

“Sarah was great with Zuko. She watched him over Memorial Day weekend for me, fed walked and gave medicine too! She took great care of him and sent lots of updates and photos.”

Molly L.

“Anna was great! She stayed the weekend at our place watching our dog Ellie who gets anxious meeting new people. Anna was very calm and patient when meeting her and I could tell Ellie would warm up fast. Thanks Anna for watching our baby and giving us peace of mind that she was well taken care of!”

Lauren C.

“Jamie was fantastic! Brody absolutely loved spending time with her. She was attentive to him and his schedule and provided updates, which is so appreciated! Will definitely schedule her for more stays.”

nicole.fundaro ..

“Sydney is a fantastic dog sitter! She was responsive and responsible with caring for our dog and our home! We give her our highest recommendation and would absolutely hire her again!”

Dillon J.

“Jeffrey stayed in our home for ~1 week, watching our cat and dog. During this time our dog needed to be coned and required a little extra care, but Jeffrey provided great care for both our animals and our home. I highly recommend him for anyone looking for pet sitting in the Medford area!”

Ellie C.

“Tori was great with Otis! We came home to a happy dog and house that looked great - can't ask for anything more! Need to firm up dates for our next trip ASAP so we can see if Tori is available.”

Sara S.

About: I have taken care of pets for animals for well over 20 years and was the manager of a pet sitting and dog walking business for a few years as well. I was also an assistant to an ethical dog breeder and helped deliver and raise a litter of teacup schnauzers. For the past year I was traveled full time in the UK and Canada as a pet and house sitter. I enjoyed it so much wanted to keep taking gigs now that I'm back in the US! I love learning the personalities of each of my pet clients and learning to adapt to their quirks. I'm getting pretty good at taking pet pics so you may get something frameable in one of my pet updates! Apart from working part time as a massage therapist on the weekends in ~4.5 hour shifts, I mostly work from home so your pet would have company more often than not. I know how to administer oral and topical medications and can be easily trained to administer IV medications if needed. I work part time in short shifts (less than 6 hours), so I will be in my clients' homes with their pets most of the time. I can provide additional references both for pet care and general care of property from airbnb reviews. I try to leave the place better than I found it and provide check ins and pictures for peace of mind.

“We had a great experience leaving our dogs, cat, and home in Annie's care! She was communicative and shared lots of photos but also gave us the freedom to enjoy our time away. The animals seemed to enjoy their time with her and the house was in great shape when we came home. Really all you can ask for! We look forward to using Annie's services again in the future.”

Taryn C.

“Rachael once again took great care of our 3 dogs for us. One of our dogs this time was sick and had a potty accident. Rachael notified us and was so understanding. She cleaned up the mess and made us feel like our dogs were in great hands. Thank you Rachael!”

Aaron D.