Dog Sitting in Jamaica Plain
Book a Jamaica Plain dog sitter to watch your dog in your sitter’s home or yours.

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Top rated Jamaica Plain dog sitters
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

“Sophia is EXCELLENT in all respects. She is very conscientious and amazing with dogs. She went above and beyond for us, addressing challenging issues in real time and responding flexibly when situations and needs changed. We are so grateful to have her caring for our dog!”

About: I absolutely love dogs, and since I don’t have one of my own, your pet enjoys my full attention in a calm, loving environment. ✨ Flexible Work-From-Home Schedule – I work remotely most of the week and can easily move around my office days to fit your needs. 🔎 Highly Attentive - I might be the most detail-oriented person you'll meet! I catch the little things, follow your instructions carefully, and make sure your pet feels safe and cared for. 📸 Consistent Updates – Expect regular photos and communication for total peace of mind. I’m home most of the week thanks to my flexible work schedule, so your pet will get plenty of attention and companionship. I’m happy to help with regular visits, check-ins throughout the day, or even last-minute requests. I understand the importance of health and safety for both you and your pet, and I am fully vaccinated against COVID-19. I work at a college in educational technology and faculty support, a role that requires organization, attention to detail, and clear communication. I bring those same skills to caring for your pet, focusing on making them feel safe, happy, and loved while I’m with them. I’m highly observant and attentive, following instructions closely and noticing even small changes in behavior. I treat your home with respect and provide calm, consistent companionship, keeping you informed so you can relax knowing your furry friend is in good hands.
“Tommy did an exceptional job caring for my two fussy cats for 6 days! My cats both need medicine and extra care every day and Tommy was consistent, reliable, and a great communicator. I can tell my cats were well cared for while I was away. Thanks so much Tommy!”

“Anastasia was so great with our young puppy. We were a little anxious about leaving her for the first time, but this was an excellent experience. Definitely booking again!”

About: I’ve always loved animals, especially dogs, and have taken care of neighborhood pets for years! I am friendly, attentive, and excited to meet your pets! Please feel free to reach out with any questions. I’m easily able to fit pet care into my schedule as I otherwise work remotely or make my own hours! Please reach out with any scheduling questions and I would love to accommodate as best I can! I will do my best to ensure your pet feels safe, loved, and healthy. I’m happy to follow detailed instructions or just stop by and assess what they need and give them some love. :)

About: Forever animal lover! I’ve always had and have loved being around animals. From playing, to walks, to feeding, happy to help you take care of your four legged loved ones. I have availability to help out with your pets in the evenings and on weekends! I’m available to stop by and play, feed, walk or just keep them company. I am able to walk your pup and take them to local parks. I can also take them out to play in your backyard as well!

“Michael is great! Responded to my request to check in on my cats so promptly and I felt secure knowing my cats were in good hands. Got lots of pictures and updates. I definitely recommend booking with him!”

About: Your dog will have an unmatched experience with me and my sweet pup, Tina! I work from home full time, so your dog will always have company, structure, and plenty of attention throughout the day. We live just minutes from the arboretum which means long, enriching walks are part of our daily routine. My pup, Tina, is 4 years old and very chill. She loves having a friend around and I’m committed to making every dog feel safe, loved, and at home and making sure they get the care and affection they deserve.
“Isabel was fantastic with our kitty! She sent great updates and photos and followed our instructions to a T. We (and Percy!) look forward to having her care for him again!”

“Jana was great with my two dogs! Sent lots of photos and info on how the visit went and she above all made sure that both dogs had a safe visit. I will definitely be using her again.”
“Sarabeth was great! She was great at reading and recognizing my dog’s boundaries, paying attention to house rules, and providing lots of fun for my dog. Will certainly have her back to watch Mae again”

“Jennifer is consistently great with my elderly cat and his multiple meds. She's also been able to roll with the punches when various things have gone wrong while I'm away, and although I wish she hadn't had to deal with any issues, it does make me feel very confident that she can handle whatever comes up!”


About: I’ve taken care of my family pet throughout her life from puppy to end of life. I am familiar with feeding, walking, providing medicine, and general companionship! I am currently in graduate school and working part-time at a yoga studio!! I look forward to adding in pet care as another part time job to get to spend time walking outside and supporting in your pet care needs! I unfortunately cannot have pets in my apartment but prioritize safety and privacy in visiting others!! I am very clean and always tidy up after myself.
“Jacqueline was great with my kitties! She was very communicative and helpful on keeping an eye on more than just my fur babies. If considering travel, you will have a piece of mind with Jacqueline caring for your pets!”

About: Hello! My name is Cynthia, and I’m a registered nurse working in primary care. I’m also a lifelong dog lover and proud owner of two wonderful dogs: Hazel, a sweet senior English Bulldog who loves naps and sunbathing, and Stella, a playful French Bulldog who enjoys playing fetch and relaxing outside in the sunshine. I live in the Roslindale area, close to spacious parks such as the Arnold Arboretum, where our dogs love going for walks and exploring. I have two children, ages 10 and 1, who have grown up around dogs and enjoy spending time with them. Creating a loving, safe, and pet-friendly environment is very important to our family. As a nurse, I am responsible, dependable, and attentive to details. I understand that every dog has unique needs, and I am experienced in administering medications and caring for senior dogs or pets that require extra attention and special precautions. I will treat your dog with the same love, patience, and care that I give my own. Communication is very important to me, and I strive to keep pet parents updated and provide peace of mind while they are away. Whether your pup enjoys long walks, playtime, cuddles, or simply relaxing in a sunny spot, I will make sure they feel comfortable, happy, and loved. I would be honored to care for your furry family member. Please feel free to reach out with any questions. I look forward to meeting you and your pup! Pet care fits naturally into my daily routine. I work Monday through Friday from 9:00 AM to 5:00 PM at a primary care office located just a few miles from home, which allows me to be available and flexible. If needed, I am able to stop home during my lunch break to provide potty breaks, meals, medications, or extra attention. I am off on weekends, giving me plenty of time to dedicate to walks, playtime, and one-on-one care. Since I have dogs of my own, caring for pets is already an important part of my everyday life. I understand the importance of maintaining routines and ensuring that each dog feels safe, comfortable, and loved while their family is away. I treat every dog in my care as if they were my own. I love spending time playing, cuddling, and giving them plenty of attention and affection. I make sure each pet maintains their regular routine and receives the care they need to feel comfortable and happy. Safety is always my top priority. I carefully ensure that dogs are securely leashed before going outside and closely supervise them during walks and playtime. I also have a spacious fenced backyard where pups can safely enjoy fresh air, exercise, and outdoor time. As a registered nurse and experienced dog owner, I understand the importance of being attentive to each pet's individual needs. Whether your dog enjoys playing, relaxing, or requires medications or special accommodations, I am committed to providing loving, reliable, and personalized care while keeping you updated for peace of mind.
About: Hi there! I’m so excited to meet you and learn more about your pet and your current needs. I know finding a sitter can feel a little nerve-wracking, so I focus on being consistent, communicative, and truly attentive to your pet’s routine and comfort. I’ve cared for animals my entire life, from Great Danes to Labs to Frenchies to teacup Yorkies. I’m comfortable with senior pets and medical needs, including administering daily insulin and following strict feeding schedules and dietary guidelines. I’m calm, patient, and detail-oriented, and I focus on helping pets feel safe and settled quickly. I don’t currently have a dog in my home, so your pet will have my full attention and care. I work from home full-time, so I’m available throughout the day for walks, playtime, feeding, and companionship. Dogs get frequent outdoor breaks and attention, and cats get steady check-ins, calm company, and routine-based care. I live directly across the street from the Arnold Arboretum, which is a wonderful, peaceful place for daily walks, and I’m also close to several dog parks for pups who enjoy more active outings. I have two children with me 50% of the time, and they’ve grown up around both dogs and cats. That being said, if your pet is not child-friendly, please still reach out. My children are with me every other week, and I’m happy to coordinate care to make sure your pet is comfortable and set up for success. I know it can feel stressful to leave your pet with someone new, and I take that trust seriously. I follow instructions closely, including feeding schedules, medications, and any special care needs, and I’m thoughtful about each pet’s comfort, boundaries, and routine. For dogs, that means consistent walks, safe supervision, and steady structure. For cats, it means calm energy, predictability, and respecting their space while still making sure they feel cared for and secure. I’m always happy to send updates and photos so you can feel confident and at ease while you’re away. My goal is simple: your pet feels safe, relaxed, and well cared for, and you feel fully informed and supported.
Jamaica Plain dog parents share their Rover experiences
I highly recommend Elizabeth for all of your dog needs. I have 2 dogs, one is reactive, and she was very thoughtful and gentle with him until they grew trust together. Elizabeth is always on time, and follows through with all her commitments. She is trustworthy, communicative, and friendly. I would recommend Elizabeth to anyone!

Madison was absolutely wonderful with my dog during her drop-in visits. She was reliable, communicative, attentive, and clearly cared about making sure my pup was comfortable and well taken care of. I appreciated the updates and peace of mind while away. I would definitely book with her again and highly recommend her to anyone looking for a trustworthy sitter!

Chelsea has been an amazing, trustworthy, and responsible friend for our pet dog whenever we go out of town and need someone for drop-in visits / walks. I have been a repeat customer, and feel 100% safe knowing that Chelsea is professional and knowledgeable about all of my dog's needs. I can fully vouch that you won't regret choosing Chelsea for all your Rover needs!

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1. Search
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Why Choose Rover?
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Reservation protection
It doesn't happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
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Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Jamaica Plain.
Rover makes it easy to find Jamaica Plain dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.

















