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

Over 389 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%.

“Lindsay was incredible with Sunny. She was very thorough during the meet and greet. She gives detailed updates with great pictures. Overall she goes above and beyond. I would definitely recommend.”


About: I’ve grown up around animals, and I’ve always enjoyed spending time with them. I have experience in dog training, boarding, walking and grooming! I work in Charlestown from around 7am-4am every day! However I am fully free outside of work hours and can spend all this time with your fur baby :) I notice things in the pets environment that they’re used to or comfortable with, and I continue to implement it. It’s of upmost importance that a pet is comfortable, especially in their own space! When I was working as a dog trainer we learned how to notice when dogs are comfortable and when they are not.

“Sent great pictures, was very communicative, and reached out as soon as she had any issues. We greatly appreciated her availability, timeliness, and friendliness while watching our three pets! Handled providing a variety of medications well.”

“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!”

“The dogs really enjoyed getting long walks with Alicia. In addition to being very sweet with the dogs, she was timely, professional, and extremely flexible and accommodating when we asked to add two days at the last minute.”


“On time, sent pictures, Katie loves her, she was able to help very last minute and went above and beyond. We couldn’t have asked for better service. Will be definitely asking for Kristen’s services again!”

“We had just moved to Boston and needed a needed a dog-sitter on short notice for our Great Dane pup, Gordon, and David crushed it! He is super-patient and confident with our big boy and expertly communicative. David will always be our “go to!””

About: I started dog walking when I was 12 years old and have been caring for animals in many ways since! I have fostered kittens, dog sat and have had many pets of my own. I currently have four cats, including a senior cat, a dog, chinchillas and a snake! I have experience with senior pets who have arthritis as well incontinence/diapering and am able to provide care for your pet no matter their age or needs. I can even give your dog a bath if it is needed. I have given baths to cats but only those with a calm temperament. I will treat your pet with the utmost love, care and respect. I look forward to meeting you and your furry friend! I have full availability, 7 days a week, to help you with your pet care needs. I am available to walk your dog (even your cat!), pop in to feed your pet and play with them, and even stay overnight to care for them when you are away. For Dogs: When caring for your dog in your home, I will walk them regularly and always respect their safe spaces. I will ensure that they always have a full water bowl and feed them when needed. If you have a particularly energetic dog, I can walk them more frequently. If your dog has a fear of storms, I will sit by them and soothe them for as long as they need to make them feel safe. For Cats: When caring for you cat in your home, I will be sure to play with them if they show interest, respect their safe spaces and if your cat enjoys walks (mine does!), I will happily take them out for a walk! I will ensure that their litter boxes are always clean, their water is full and feed them when needed.
About: I've had dogs in my family since I was a child, continuing into adulthood. As an adult I raised and trained two dogs from puppyhood to senior citizens. I have experience with taking dogs to obedience classes, training them on recall and basic commands, and using positive reinforcement. Lots of experience with puppies and adolescent dogs. I have experience with rescues, fosters, and dogs with trauma histories and pick up dog body language fairly quickly. I know that you the owner know your dog best and as a pet parent myself make sure to respect preferences, notes on behaviors and routines, and make their experience as consistent and stress-free as possible, for them and you. I am fairly active in my day to day life, and love doing shorter and longer walks with dogs. I take mine to the dog park too, but understand that isn't for every dog, there are plenty of enrichment activities to do with them outside of public spaces. I am currently going to school and have a fairly flexible schedule to work in care throughout the week and my availability should be fairly routine. In/near my own home I have access to green spaces and a dog park. Plenty of space to walk a dog. At a clients home I would follow applicable routines and instructions regarding walks, enrichment, and socialization, which could include walk, dog park visit, or activities in the home.
About: I’ve always had at least two dogs in the house, and have always loved caring for cats! I have plenty of experience taking care of horses and chickens, and I’m no stranger to taking care of many pets at one time, for example, 3 large dogs, 3 cats and 3 horses at the same time! I’m currently a college student at Berklee College of Music, which makes my hours fairly flexible, as well as having easy transportation being in the heart of the city! Though my weekly schedule varies, my weekends are very open for full-time care, and I can easily work around my school schedule to give your furry friends their routine as smoothly as possible 😊 I live in a condo with two elderly chihuahuas (almost 15 years old!) named Glory and Hero, as well as a super loving mutt rescue named Mysti! I love going for long walks with Mysti, and taking my chihuahuas for nice short walks as they get older. Making sure Mysti gets the proper exercise and attention is super important as she is a medium sized dog in a condo, as well as accommodating my older dogs as they age.
About: I’ve been caring for pets since childhood, starting with my own dog at age nine. In middle school, I regularly walked my neighbors’ dogs and have since provided dog sitting, cat sitting, and general pet care for friends whenever needed. Whether it’s walks, playtime, or simply keeping pets company, I always treat them with love, patience, and attention as if they were my own. I'm currently a senior at Florida State University with a very light course load, so I have free time early in the mornings and in the afternoons. I also am working currently on the days that I do not have class, but my work schedule also allows me to pet sit in the early mornings and afternoons. When caring for pets in a client’s home, my top priorities are safety, trust, and creating a comfortable environment. I follow any specific instructions closely, from feeding schedules to medication routines, and always make sure doors and gates are securely closed. I treat every pet with patience and kindness, keeping them active, entertained, and cared for while respecting the home.
“I was initially super anxious about using this service, but Stephen put my mind at ease with incredible care, kindness, and communication. Amazing sitter, went above and beyond. Thank you!!!”

About: I dog and house sat through my entire high school career! It’s one of my great joys in life. I love to meet and take care of new dogs and I’m very diligent about leaving spaces better than I found them! I would volunteer to take care of my friend’s pets whenever they went out of town! I’m a full time student out of town in Boston, but I dog sit for work during the summers! So during the summer months when I’m home, I am free pretty much every single day for work. I always make time to not only walk dogs in my care, but to play with them and make sure they aren’t left lonely! First thing when I arrive is to take them on a long enough walk to ensure that they’ve gone both #1 and #1. Then we come back inside and I’ll check their food and water. If at any point have to leave my house, I have a very large pantry with dog beds and food/ bowls. This is where I usually leave dogs while I’m away. When I’m home, I let the dogs out so wander as they please. It’s very cosy. I also have two other small dogs that are very easy going and cooperative with new dog friends! They aren’t violent in the slightest.
About: I have 6 years of hands-on experience raising and caring for my own dog, which taught me the importance of patience, structure, and genuine love. I understand that every pet has a unique personality, routine, and needs. Whether it is providing structured daily walks, fun playtime, sticking to strict feeding schedules, or simply offering a calm and comforting environment, I treat every dog with the exact same level of devotion, warmth, and attention as my own. I currently have a very flexible schedule with plenty of open availability throughout the week and on weekends. This allows me to dedicate quality, uninterrupted time and attention to your pet. I can easily accommodate daytime visits, afternoon walks, and full-day companionship to ensure your dog never feels lonely and maintains their normal potty and feeding routine seamlessly. Safety, comfort, and open communication are my top priorities. When hosting pets at my home, I provide a peaceful, clean, and dog-safe apartment where your pup can relax and feel right at home. For outdoor walks, I always keep dogs securely leashed and stay mindful of surroundings and weather. I am also happy to send regular photo and video updates so you always have total peace of mind while you're away!

About: I've been caring for animals for many years and have experience with a wide variety of species. I've been handling and looking after dogs and cats since I was 12 years old, giving me years of hands-on experience with pets of all ages, personalities, and needs. Whether it's feeding, walking, playtime, administering basic care, or simply providing companionship, I always make sure every pet feels safe, comfortable, and loved. I currently have a cat of my own, so I understand how important it is to trust someone with your furry family member. I treat every pet as if they were my own and strive to provide reliable, attentive, and compassionate care while you're away. I'm currently taking some time between finishing graduate school and starting my postdoctoral position, which means I finally have something scientists rarely get—free time! I've decided to spend it doing something I genuinely enjoy: caring for animals. This flexible schedule allows me to dedicate plenty of time and attention to each pet, whether that's stopping by for visits, playing, feeding, administering medication, or simply keeping them company. I know every dog/cat has their own personality (from "cuddle enthusiast" to "please admire me from across the room"), and I'm happy to adapt to whatever makes them feel most comfortable. For me, pet sitting is the perfect way to combine my love of animals with helping fellow pet owners have peace of mind while they're away. Your pet's safety, comfort, and routine are always my top priorities. I understand that every cat is different, so I take the time to learn their individual personality, preferences, and daily routine to help them feel as relaxed as possible while you're away. When caring for pets in a client's home, I respect both your home and your pet's established routine. I'll follow all feeding schedules, walks/litter box maintenance, playtime, medication instructions, and any special requests you have. I also make sure doors, windows, and gates are secure at all times and keep a close eye on your dog's/cat's behavior and well-being. I'm happy to provide regular photo and video updates so you can see how your dog/cat is doing and have peace of mind while you're away. My goal is for your pet to feel safe, cared for, and loved until you're back home.
The median cost per visit for dog sitting in Jamaica Plain is $25
Dog parents share their Rover experiences - Jamaica Plain
Lorena & Jahn are wonderful with our pup Caddie! Caddie is a young, energetic puppy, and they were extremely helpful in keeping her happy and engaged during her 30-minute drop-in visits. They communicate very well, giving us updates at each drop-in visit with photos. We will definitely book with Lorena & Jahn again! Highly recommended

Alexandra filled in for us super last-minute due to a cancellation, and not only read through the list of what to expect with our dog / what we needed for a visit, but was patient with our dog meeting a new person, took extra photos, wrote up a through ‘report’ after the walk + visit, and was extremely responsive via messaging. Couldn’t ask for more!

Tess looked after my puppy for me while I was at work this summer and I couldn’t think of a better person for the job! She was so communicative and detail oriented, took great notes on his eating and bathroom schedule. My roommates continuously commented on how sweet she was with him and how well he did with her! I couldn’t recommend her more!!

Amanda was punctual, communicative, and clear about what my dog Charlie was doing. Most important, she was sweet and kind to Charlie, giving her belly rubs and love. I appreciated her kind demeanor and how responsible she was in leaving everything the way I requested. I would request Amanda with enthusiasm next time I need someone to come walk and watch Charlie!
Ella was amazing to work with. She was super responsive and took excellent care of Blue. I loved how much feedback she gave in her rover cards. It was such a weight off my shoulders to know Blue was in good hands while I was away. I will definitely ask Ella to watch Blue again in the future.

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 Dog Sitting - Jamaica Plain
Frequently asked questions about Rover
The average cost for Dog Sitting in Jamaica Plain on Rover is $26.25 per visit (as of September 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 September 2026, there are 10,399 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:
- 90% 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.
















