Dog Sitting in Winthrop

“Lauren checked in on my cat Belle while I was away and was amazing! Greatly appreciated the photo and vid updates and super responsive!! Definitely recommend”

Kate L.

“Kyle took amazing care of our cat while we were away. Our reserved kitty warmed up to Kyle immediately and Kyle was extremely warm and responsible. We would be happy for Kyle to watch our pets again soon!”

Margaret F.

“Tawana took amazing care of my senior cat with health issues and navigated the various medications like an absolute pro. I am looking forward to working with her again.”

Cosima B.

“Chloe did a great job with my two cats! From the pictures, they warmed up to her quickly and were happy and healthy upon my return. Chloe followed the care instructions immaculately and was always punctual. I would 100% recommend Chloe!”

Nolan G.

About: I'm a lifelong animal lover with years of hands-on experience caring for both dogs and cats, including multiple senior dogs and dogs with anxiety. My entire family has had, or currently has dogs, so I’ve been surrounded by furry friends my entire life! In the past, I've trained my own dog to sit, lay down, shake, and even dance—so I know how much time, love, and patience pets need. I also understand how important it is to find a sitter you can truly trust. I’ll treat your pets like they’re my own, giving them attention, affection, and reliable care. My wife and I dream of one day owning a personal farm where we can give even more animals a loving home. Until then, I’m here to provide your pets with the next best thing—a safe, happy, and caring environment. I'm a musician, so my schedule is a bit more flexible and less traditional—which works perfectly for giving your pet the care they need, even on short notice. I'm most available during the day, but I understand that things can change quickly in life, so I do my best to accommodate last-minute requests too. Whether it's a quick walk or some quality time while you're away, I’m here to help keep your pet happy and comfortable! When I found my dog, Rhythm, in college, she quickly became my best friend and my whole world. From the start, I felt a deep responsibility to keep her safe—like I was the only one who truly could. That experience taught me how important trust is when it comes to our pets. I understand how hard it can be to leave your pet with someone new, which is why I prioritize safety and care above all else. Every pet is different and deserves personalized attention, and I’m committed to making sure they feel secure, comfortable, and loved while you're away.

“Alexis did an amazing job caring for my dog. He’s big and he has a lot of special needs. Alexis was extremely reliable and caring, making sure his medical needs were met and giving him lots of loving. Highly recommend!”

Blake R.

About: Hi there! I’m Melissa, originally from the Boston area and I service in and around Boston. I’ve been working with Rover for over 6 years and have more than 12 years of experience in pet care overall. I offer dog sitting, walking, and drop-in visits, and I’ve cared for pets of all ages, breeds, and temperaments—so I’m well-prepared for just about any situation. I also offer services to cats 🐱 I grew up with two Staffordshire Bull Terriers and often helped care for neighbors’ pets. During school breaks, I volunteered at my local animal shelter, gaining even more hands-on experience with dogs and cats alike. I’m also comfortable caring for cats and have pet-sat for many feline friends over the years. Above all, I’m a true animal lover. I genuinely enjoy spending time with pets and treat every one of them like my own. I’d love the opportunity to care for your furry family member! I have a flexible schedule and availability. Currently available Monday-Sunday for services. Please let me know your schedule and prospective days you will be needing services. Cancellations are allowed up to 24hrs beforehand. Depends on what the particular pet needs. Typically I like to meet the pet first, especially if it will be a reoccurring visit. I would like them to be comfortable with me by the time I arrive to care for them. As well as I asked clients on the type of home they may have just to understand the environment better. If the client is comfortable, I’m also open to visiting their home before a house sit so I can get a better idea of the environment I will be taking care of the pet.

About: I’ve owned both dogs and cats and understand the unique needs of each. I’ve cared for, fed, and walked dogs with love and attention, and have experience training puppies, administering medication, and supporting senior dogs—including those with back issues who need gentle care. As a devoted cat owner with two of my own, I’m also experienced in feeding prescription diets and giving medications to cats. Whether it’s playtime, walks, snuggles, or special care, I treat every pet like family and make sure they feel safe, happy, and well cared for while you’re away. I’m currently working remotely, so I have plenty of time to shower your furry friends with care and attention! I’m available for drop-in visits or walks anytime during the week or on weekends. I provide all care in your pet’s own familiar environment, which helps reduce their stress and keeps their routine consistent. During drop-in visits, I focus on giving plenty of attention, playtime, and affection while following any specific instructions you provide.

“Roxana took wonderful care of our cats! She was very communicative and sent us tons of photos to show that they were eating and that the litter boxes were cleaned, etc. Would definitely book again!”

Becca S.

“Kayla took awesome care of my kitty! My cat Rory is incredibly shy and scared of people, but Kayla was able to make a connection with her! I’m glad Rory was able to receive some affection and play while I was away. I felt so much relief knowing that she was being looked after by someone she felt comfortable with.”

Sarah S.

About: I’ve always lived with dogs at home with my family, with up to four family pets at once. I’ve taken care of many family friends’ doggos and have built other client relationships too for the past three years. I have experience caring for dogs with specific diet and medication needs and a pregnant mama dog. I’m currently a graduate student with a flexible schedule when I’m not in class or lab! I love an excuse to get out for a dog walk or some pet play time. I’ll stick to your pet’s regular routine, whether they love to get out and about to explore or are a homebody. I’m happy to accommodate any particular needs for your pet.

“Judy was extremely attentive and prompt. She did a wonderful job of keeping us updated through messages and pictures! Our cat seemed to really enjoy her company and all the attention she gave him. Would highly recommend Judy and we will be using her in the future!!”

Samantha M.

About: What sets me apart from other sitters is my lifelong, hands on experience with both dogs and cats. I’ve owned pets my entire life, including those that were fully house trained as well as those that needed more attention and patience. In addition to caring for my own animals, I’ve dogsat for friends and family over the years, which has given me experience with a variety of breeds, personalities, and routines. I'm comfortable handling pets with different energy levels and needs, whether it’s giving extra attention to a senior pet or helping keep a young pup on track. My approach is always calm, consistent, and caring; treating every pet as if they were my own. I work full, but that does not stop me from caring for animals. I have taken care of various pets while being a full time student. My week nights and weekends are always open to be fully involved with your pet! I always have a watchful eye, having years in experience as a camp counselor and having to make sure young ones stay safe. I also am patient with animals and understand for both of us to be safe, we must be respectful to each other.

About: I’ve been caring for dogs since I was 15, and my love for them is immeasurable—they are truly angels on earth! What sets me apart is my deep understanding of dogs of all ages, from playful puppies to gentle seniors. I provide personalized care, patience, and lots of love to ensure every pup feels safe and happy while you’re away. Whether it’s cuddles, playtime, or extra attention for older dogs, I treat every dog like family! As a paralegal, my schedule allows me to dedicate my Monday afternoons and weekends to caring for dogs. This gives me plenty of time to provide attentive, loving care—whether it’s walks, playtime, or cozy companionship. Since I genuinely love spending time with dogs, pet care is the perfect way to fill my free time with something meaningful and joyful! Whether caring for pets in my home or my client’s home, I prioritize their comfort, safety, and happiness. I tailor my care to each dog’s needs—whether that means sticking to their usual routine, providing plenty of playtime, or offering extra snuggles for anxious pups. In My Home: I create a cozy, stress-free environment where dogs feel at home. They’ll have plenty of space to relax, play, and receive one-on-one attention. In My Client’s Home: I ensure pets feel secure by maintaining their regular schedule, whether that’s feeding, walks, or bedtime routines. I also respect their space and provide companionship so they never feel lonely.

About: I’ve loved animals for as long as I can remember. I got my first dog—a giant, goofy Labrador named Riddle—when I was 12. He still lives with my parents, and caring for him taught me a lot about large-breed dogs, from daily exercise needs to managing food motivation and leash manners. In 2022, I adopted my cat Milo from a local shelter. He’s taught me patience, the power of routine, and the art of earning trust—especially with more reserved or independent pets. Between Riddle and Milo, I’ve had experience with both high-energy dogs and gentle, sensitive cats. I’m comfortable feeding, grooming, cleaning litter boxes, administering oral meds, and giving pets the attention they need—whether that’s play, quiet companionship, or lots of snuggles. I care for every pet like they’re part of the family. I bring a calm, gentle presence, and I always pay attention to each animal’s personality and preferences. I have experience with both puppies and adult pets, and I’m especially attentive to signs of stress or discomfort so I can adjust accordingly. Whether your cat is shy or social, I’ll make sure they feel safe and cared for while you’re away. My schedule is reliable, and I’ll always keep you updated with photos and notes so you have peace of mind. I’m a young professional living and working in Boston. I work from home three days a week (Monday, Wednesday, and Friday), so I have plenty of flexibility on those days to check in on your pets throughout the day. On Tuesdays and Thursdays, I commute to downtown Boston for work, but I’m available for evening visits around 5 PM or later. My weekends are usually low-key and flexible, making them a great time for drop-ins, walks, or extended pet care. I’m naturally cautious, so I take extra care to keep cats safe and comfortable. My home is fully cat-proofed from bottom to top, and I maintain a calm, clean environment. In your home, I follow routines closely, keep spaces tidy and secure, and always double-check doors, windows, and feeding instructions. I know how it feels to be away from your cat—I’m the type who stares at the pet cam all day when I travel—so I’ll send regular updates with photos and notes to give you peace of mind.

“Michelle is great with our cat! He always enjoys her visits! She’s very reliable and super great to communicate with! Thank you so much Michelle!”

Bridget M.

About: If you're looking to teach your dog how to heel during walks, reduce leash pulling, or simply help them be less reactive to the bustling outdoor environment of Boston, I offer private training lessons focused on basic dog obedience. I've always had a deep love for pets and have spent years honing my skills in animal training. With extensive experience and knowledge gained from reading numerous obedience books, I’ve successfully trained both dogs and 1 cat in basic obedience. My own dog, Sully, is a certified pet therapy dog with the Pets and People Foundation of Massachusetts and also holds a Canine Good Citizen (CGC) certification, demonstrating my commitment to high standards in training and care. I'm currently a full-time worker (M-F), but I am actively looking for gigs after 5pm. I am free on the weekends from 8AM to 6PM, or as needed. I have a dog as well, so I do not do overnight stays in your home, sorry! But I can always offer boarding 🫶 I prioritize understanding and responding to each pet's unique needs, ensuring they feel comfortable and secure. By closely observing their behavior and cues, I can quickly identify what they might need in the moment, whether it’s comfort, play, or rest.

“Thank you so very much Kayla for your patience, excellent communication, and flexibility with this latest session with Atlas!! Words simply cannot fully describe my gratitude!”

Rachel W.

About: Hi there! I’m a 30-year-old flight attendant for a major U.S. airline—so I enjoy an extremely flexible schedule with up to two weeks off every month. Raised alongside dogs both large and small, I’ve been walking, sitting, and showering love on furry friends for as long as I can remember. While living abroad, I volunteered at the local humane society—taking dogs on beach adventures and even fostering puppies until they found their forever homes. I have a seven-year-old island mutt, whose boundless energy inspires our daily walks and frisbee sessions. You can rest easy knowing I’ll treat your dog like family, keeping them active, happy, and safe while you’re at work or away… and don’t worry, you will receive plenty of photo updates! Message me today for a free 15-minute meet-and-greet—I can’t wait to meet your pup! I enjoy an unusually flexible calendar—up to two weeks off each month and predictable travel—so with just a few days’ notice I can carve out dedicated time for your pup. Here’s a snapshot of a “typical” week when I’m home. • Mornings (6–9 am) – Early walks around the neighborhood or on the beach—great for high-energy breeds to burn off steam before you head to work. – Quick drop-in visits for breakfast feeding, potty breaks, and belly rubs. • Midday (11 am–2 pm) – 15 to 45 minute walks or play sessions in a secure yard or local dog park. – Just need simple cuddle time? I can do whatever your dog needs most. • Evenings (5–8 pm) – Evening walks or a fetch session—perfect wind-down before bedtime. – Dinner feeding, nighttime potty break, and a sleepy snuggle to help them feel safe. • Days Off – Overnight stays in your home, ensuring constant comfort and companionship for your peace of mind. What to Expect • Daily photo/video updates • Last-minute booking flexibility—if your work hours change, just drop me a text! I know nothing’s comfier than their own couch, so I prefer in-home visits. Here’s what to expect: • Respect for your space—shoes off at the door, home security top-of-mind, and I follow any “no-go” zones you set. • Routine follow-through—meals, medications, potty breaks, walks and play all happen exactly on your schedule. • Clean & cozy—accidents happen, so I can ensure I will clean and you will not come home to a mess. • Updates & transparency—daily photo/video check-ins and a quick log of their meals, walks and mood.

About: I've cared for dogs my entire life, from puppies to seniors. I'm super patient, sweet, and absolutely love kids and dogs. Your pets are in great hands! Pet care easily fits my routine, with a part-time job & free time, I'm flexible. Having my own pet, I've been looking for something like this to share my love for animals! I mainly prefer to go to your house to take care of the pets. I do have a yard in the front, which is a bit small but enough for a small to medium-sized dog. Plus, I've got space in my apartment as well!