Dog Sitting Jamaica Plain
Book a Jamaica Plain dog sitter to watch your dog in your sitter’s home or yours.
Over 409 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%.
“This is the second holiday season that Madison has taken care of our two cats while we were traveling and knowing she was checking in on them made it a wonderful and relaxing trip. She is consistently excellent, sends the best rover cards and pictures and the kitties absolutely adore her. She goes above and beyond and I really cannot recommend her highly enough!”
About: I’ve worked with dogs and cats for the last few years as I’ve been working on my bachelors and masters degrees. I love spending time with animals and would have a dog or cat of my own if I didn’t enjoy occasional trips as much as I do! I love being outside and work well with active pets. I’ve provided some basic medical care, such as pill administration and wound care for dogs. I’m currently working part time remote and in office and really enjoy spending extra time I have with pets. I’m especially free for weekends/extended weekends. I offer pet sitting services for clients in their home. I typically will try to get dogs on two long walks/dog park visits/hikes a day depending on what’s agreed on prior and the dogs’ fitness abilities. I also love hanging out with cats and playing with them during the day. Your pet can expect lots of pets and and quality time with me as a sitter.
About: I have been around dogs for a majority of my life and feel extremely comfortable around almost all breeds. I am currently the proud mom of a 8.5 year old Siberian Husky, so I am use to being around and providing care for high energy dogs that require a little extra exercising. I currently live in a an apartment complex with access to many parks and green spaces which I am more than willing to take your dog to during our walks together. I am equipped with the many skills it takes to provide the best care for you dog and am willing to work with you to get that done. I am available for drop in visits M-F in the mornings and after 3 pm. I am available most weekends (F-S) at any time of day for boarding, drop in or walks. I leverage my extensive pet care experience to ensure pets get regular exercise, proper nutrition, and mental stimulation. My current living situation allows me to best fulfill all of a pets’ needs. When caring for clients' pets, I follow their established routines and preferences, provide regular updates, and ensure the safety and cleanliness of their home. Consistency and respect for the pet's needs and the client's home are my top priorities.
About: Howdy! My name is Natalie and any dog I've met I have loved like my own. Growing up I had my fluffy 90lb Labradoodle and two sweet guinea pigs. Aside from my own pup, neighbors, friends, and family have relied on me to walk and feed their dogs and care for their cats. I currently have a full time job where I have to go into the office Monday-Thursday but an available for walks and drop-in on Friday, Saturday, and Sunday. I live in a small apartment in Brighton MA across the street from a wonderful reservoir and less than a mile away from several parks! I am a very active person so would be a great host for an athletic or active dog! However, if your dog is less active, I can easily bring my activity level to where your dog is happy and comfortable. I allow pets on my bed and couch, unless you prefer them not to.
About: I am a true dog lover and plenty of experience as I have dogsat many times throughout the years. I have had three dogs myself so I understand the responsibility and care that each dog needs! I love animals and love spending time outside with them! I just moved to Jackson and do not start work until the end of April, leaving plenty of time to take care of your pet! My schedule is very flexible so if you need any specific care, I am available. I love to be outside and doing so with a pet is even better! I enjoy walks and hikes, whichever you are most comfortable with.
About: I had pets since young: Guineas, turtles, cats, dogs. I have also trained my pets mainly cats and dogs who are high energy or lazy. I also help a cat give birth to kittens and litter trained the kittens. My schedule varies since I am enrolled in college but also allows flexibility. I am available mainly in afternoon and evening but sometimes even mornings. My care depends on the personality and needs of the pet. If the pet is fearful then my movements may be limited or if they enjoy people I will interact more.
About: I am currently a graduate student with a flexible schedule looking to spend some free time racking up that dopawmine! I have grown up with dogs and cats for my whole life and although I do not have my own furry friend right now, I adore pets and would love to share that with your pet! I have experience house sitting for a family with 3 medium sized dogs and am comfortable with dogs of any size. I also love to go on walks and stretch my legs, what would be a better addition than a doggo companion! Although I love dogs, also have experience with cats and love all from snuggle to sass! My camera roll is essentially filled with dogs and I would love to send updates throughout my walk/stay with your pet! I would be overjoyed for you to let me share some of my love with your furry friend! Please reach out, can’t wait to hear from you and yours 🐾. I am a graduate student at Northeastern with a flexible schedule. Because I have no pets of my own (yet!) I have a very open schedule! I am very comfortable walking on leash with dogs and am happy to do feedings and potty breaks! I appreciate clear instructions tailored to your pet to make them as comfortable as possible in their routine.
“Marlee watched our cat George for a week while we were away. They were an ideal sitter! Punctual, accommodating, and kind. They sent us plenty of updates and pictures, and played with George each visit. Really kept us at ease while we were on vacation, and we'll definitely be reaching out to them to watch George again in the future.”
“Ailise did a great job checking in on our dog, Ollie! He’s a nervous & anxious dog who likes to bark with unfamiliar people, but she did a great job making him feel comfortable. She cuddled with him on the couch and sent us pictures! Would 10/10 recommend Ailise!”
About: I was a dog walker in Back Bay and South end for a year and provided loving care to all the dogs I worked with. I have also worked with all sorts of animals at an AZA accredited zoo in upstate New York for 5 year and have learned about how to care for animals in all capacities wether it be cleaning enclosures or giving out enrichment. Im available all week days for walks and weekends for boarding! I’d be happy to provide care for your pup at anytime during the week! I have a nice big apartment in Brookline next to a park where I’m happy to take your pup for some enrichment when hosting. I will follow any guidelines set to make sure your doggo gets all the proper care they need
About: I’m Melissa, your pet’s newest fan and soon-to-be best friend! As a lifelong animal lover with a passion for the scientific world of medicine, I’m actively pursuing a veterinary career 🐾👩🔬🩺 I’m a recent university graduate staying in Boston during my gap years so I’d love nothing more than to spend my new-found free time caring for your pet! I currently have no pets of my own at home but have spent years playing, watching over, and caring for family and friends’ pets, volunteering at animal shelters/rescue organizations, and learning more in-depth about animal behavior + biology through my college courses. Leaving your pet in someone else’s hands can be stressful for you and your fuzzy family alike and I’m here to do everything in my power to reduce that anxiety for you both. You can count on the most detailed updates including photos, videos, and calls (if requested) to keep you in the loop about what your pet is up to during your time apart, how they’re feeling, any new friends made, and more! I truly believe that communication is key and I will go above and beyond to ensure that you get honest, detailed, and reliable information while you’re away. Your pet’s happiness and well-being are always my top priorities, and I take pride in creating a safe, joyful environment for them. As someone who is dedicating their life to supporting the health and safety of all animals, I promise to love, cherish, and care for your cat or dog as though it were my own! I swear not only to do no harm, but to leave no head un-pat, no tail un-wagged, and no cat or dog lacking in loving care while under my watch 🥰 I can’t wait to meet you and your furry friends! My current WFH schedule is very flexible so I can care for your pet as needed. 😊 I’m available to provide frequent potty breaks and walks not just during a lunch break, but whenever you feel like they need a drop-in visit while you’re busy. I’m also more than happy to come by and visit, play with, and/or clean after your cats whenever you need. Whether you need morning, afternoon, or evening, I’m free to attend to all of their needs! Looking after your pet is not a responsibility I take lightly; I don’t believe there is such a thing as being “too careful” when it comes to safety! I’m very mindful of the objects, toys, and food items your dog and/or cat may encounter at home or outside. Any notes on behavior around other animals as well as potential quirks, triggers, or sensitivities are all incredibly useful things to let me know so I can keep your pet and myself safe during our time together ☺️ Safety and communication are always #1! (*I don’t provide cat or dog sitting/boarding services at my home currently)
“My babies were well taken care of. Christopher is willing to accommodate last minute request. Good communication to make sure things go well. Will book with Chris again.”
“Magdalena was wonderful! She was very communicative and did a great job of looking after my slightly elderly cat. I really appreciated all the extra cuddles she gave Scarlet”
The median cost per visit for dog sitting in Jamaica Plain is $25
Dog parents share their Rover experiences - Jamaica Plain
sydney visited bubba multiple days while i was working all week, i came home to a happy and tired dog, and she was clear with communication and providing updates and taking care of bubba. she made sure to follow instructions well and take great care of bubba. thanks so much sydney, will definitely use you in the future to watch bubs.
Alissa was absolutely amazing with my husky. She took great care of her, great communication, and very good at accommodating my dog’s needs. I felt very safe knowing that my girl is being taken care of. I definitely will be booking with her again and I highly recommend her :)
We chose Caleb because he was a cat-forward sitter, and he took great care of our special needs cat! She received plenty of attention and all of her medications as needed. Caleb shined even more caring for our aging and declining senior dogs who started needing extra attention as our trip came closer. We greatly appreciated Caleb and would happily rehire him!
Elli was an absolutely great sitter for our Cocker Spaniel. She responded to our Last Minute Request very timely and allowed us to have an evening out of hotel without Winnie while traveling. She was early for Start Time and extremely flexible with our request to be a little late. Clearly she took great care of Winnie!! Very professional with communications. Would highly recommend Elli for taking care of your pet!!
Anthony was absolutely amazing! He was originally scheduled to watch my dog Echo from 7–9 PM EST, but when I needed to change the time to 2–4 PM, he was incredibly accommodating and flexible. His communication was excellent, and he was extremely responsive throughout the entire process. He is friendly, approachable, professional, and genuinely great to work with. It was clear that he was reliable and willing to help make things easier for me. I truly appreciate his flexibility and the outstanding service he provided. I would absolutely recommend Anthony to anyone looking for a trustworthy and dependable dog sitter. I would definitely book him again! 10/10
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.
How to book dog sitting
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
It's that easy! All payments are processed through Rover's secured platform.
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 of Dog Sitting in Jamaica Plain is $27 per visit as of October 2026. Most bookings cost between $14 and $43 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 10,347 sitters on Rover offering Dog Sitting across Jamaica Plain. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 .
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 , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
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:
- 85% of sitters can help with special care needs
- 90% can help with giving oral medications or injections
- 94% 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 , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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