Dog Sitting Jamaica Plain
Book a Jamaica Plain dog sitter to watch your dog in your sitter’s home or yours.
Over 406 pet parents in Jamaica Plain have booked dog sitting
Jamaica Plain, Find top rated dog sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Alicia did an amazing job with Chica and Benji! Benji went on multiple long walks, longer than we would even expect in the winter and Chica got lots of attention. Alicia was very communicative and friendly. We would highly recommend her.”
About: I’ve been around dogs my whole life and have experience caring for both small and large breeds. Back home, I have two dogs—a Bernese Mountain Dog and a Samoyed—and I’ve spent years walking them, playing with them, and making sure they get the exercise, attention, and care they need. I’ve also cared for smaller breeds, including Shih Tzus, so I’m comfortable adapting to different sizes, personalities, and energy levels. Whether your dog loves long walks, playtime, or just wants companionship, I’ll make sure they feel safe, happy, and well cared for while you’re away. I work in research at Brigham Women’s Hospital and usually finish around 3–4 PM, so after that I have time dedicated to pet care. On weekends, I’m available for the full day. When caring for pets in a client’s home, I always respect their routine and follow the owner’s instructions closely, including feeding schedules, walks, medications (if needed), and any special preferences. I understand that staying in a familiar environment helps pets feel comfortable and secure. I make sure they receive plenty of attention, exercise, and companionship while keeping the home clean and treating it with the same respect I would my own. My goal is for both you and your pet to feel safe, comfortable, and worry-free while you’re away.
“Connor was amazing. She was reliable and I fully trusted that my fur babies were well taken care of while we were gone and enjoy our vacation. She provided daily pictures and updates! I’d book again.”
About: I’ve taken care of neighbors & family friends dogs since middle school, doing drop-ins, walks & overnight stays. I also have experience with senior dogs, both my own & friends’ who I’ve cared for. My childhood dog, and best friend, passed away almost two years ago, and as a huge dog lover, I’ve been missing having a pup in my life! I would love to love yours <3 I work a full-time job, but am hybrid, so I’m only in the office Tuesdays & Wednesdays! I can do walks in the mornings before work on Monday or Friday, after work any day of the week (adjusting for the commute on Tuesday/Wednesday), and can be free on the weekends! If you’re near where I live, I could also pop in during the work day on my remote days. Unfortunately our apartment doesn’t allow dogs :( But I will follow your lead on what works best for you & your pup(s) in your space! I want to make sure everyone feels comfortable with the routine & arrangement!
“James was an excellent caregiver for my cat. He came over early to see the house and meet Finbar, sent nice updates and pictures. I would be happy to use his services again.”
“I wish I could give more than 5 stars because Kristen is just that good! We had an emergency this morning and Kristen was able to come last minute to take care of our pups. She did so fully knowing that there would likely be a crate full of poop when she arrived. She is so great with our pups and we trust her completely!”
“Ayana was great! We went away for the holidays and wanted someone to watch over and feed our cat while we were gone. Instead of sheltering her at the vet or a cat hotel where she’s probably spend most of her time in a kennel we liked the idea of keeping her in her own space. Ayana had great energy about her and showed a knack and true fondness for animals. She was an excellent communicator and was very attentive and sent many updates with pictures, which helped ease our minds. We highly recommend her services if you’re in need!”
“Jana was a perfect dog sitter! She accepted the job on very short notice and arrived early. She really saved the day! She was very gentle and loving with my tiny chihuahua puppy. I loved getting the picture updates. Thank you, Jana!”
“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!”
“Ella was perfect! Our animals absolutely loved her! Her timing was perfect and she was very helpful with every request we had. I can’t recommend her more and I’ve had many Rovers!”
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.
About: I found my love for animals volunteering at MSPCA adoption events, and carried that passion through college as a part-time kennel attendant caring for dogs and cats of all kinds. I also raised my own dog until she passed away from cancer last year, and that experience only deepened my appreciation for how much the animals in our lives mean to us. I’d love nothing more than to pour that love into caring for yours! I currently work hybrid so I have a lot of time to go on walks and play with your pet! I'm generally available on weekdays after 3pm or house sitting Fri-Sun. In your home, I am very clean and respectful and will abide by any rules you may have. Please let me know how regularly you would like updates, as I would be happy to take lots of photos and videos!
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.
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.
About: I have done a lot of animal sitting since I was in high school looking after my nieghbors dogs and cats when they were away. I am a huge animal lover but I am best with dogs and cats. Before I went to college my nieghbor had just bought a puppy and we had just got a cat, I trained the cat and I did most of the dog walking for the puppy. Being able to play and care for animals is the best job I can think of. I can’t wait to meet your fur baby! I would love to be able to work with familiar clients and their animals. I provide over night pet sitting services, dog or cat walking, and drop in’s. I can take care of your fur babies Friday to Monday, for anything outside that time I may have availability, so just ask! I work a full time job 8am-4:30pm Monday to Friday. I typically go off the rules you lay out for your pet along with their usual routine. I want to make things as easy as possible for you and your pet. If you have a list of dietary restrictions or medication they need to take, I’m happy to learn as well as get them the care they need. If they have a specific dinner or walk time, I want to make sure I stick to it for you.
The median cost per visit for dog sitting in Jamaica Plain is $25
Dog parents share their Rover experiences - Jamaica Plain
Liza is a professional and we will certainly keep her in mind for any future needs. She was extremely attentive to the specific needs of our pups, ensuring that she had all the instructions/details ready to go before we even left for our extended trip. Her Rover cards/visits were thoroughly documented and her communication was top-notch, giving us the peace of mind we needed to enjoy our vacation. Our pups easily fell in love with her! She’s a no brainer to hire!
I needed last-minute care for my dogs, and they were incredibly helpful and responsive. Meaghan communicated well throughout the visit, and sent plenty of updates and photos, which gave me great peace of mind. Most importantly, my dogs were comfortable with her right away, and it was clear they were well cared for. I would absolutely recommend them to anyone looking for a reliable and caring pet sitter!
Gabriel was wonderful with my pups! He was very communicative and flexible with my whacky schedule, and he took the time to come over in advance to meet them first and introduce himself so they wouldn’t be meeting a strange for the first time during their drop in. I can’t recommend him highly enough!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for dog sitting - Jamaica Plain
Select a filter and find qualifying sitters offering dog sitting.Sitters in Jamaica Plain average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Jamaica Plain
Frequently asked questions about Rover
The average cost for Dog Sitting in Jamaica Plain on Rover is $22.2 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 10,511 sitters on Rover offering Dog Sitting across Jamaica Plain. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Jamaica Plain stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Jamaica Plain choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Jamaica Plain with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Jamaica Plain. On Rover:
- 91% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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