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%.
“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.”
“Nick was great with our cat Delilah! He was very professional and came and met her ahead of time. She was very comfortable with him as we saw through many cute photos! We would definitely book with Nick again.”
“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 have 5 years of experience caring for dogs and truly enjoy making every pet feel safe, comfortable, and loved. I’m dependable, patient, and attentive to each dog’s individual personality and routine. I’m happy to help with walks, feeding, playtime, potty breaks, and plenty of affection. I have experience with elderly dogs as well as medication schedules and any special accommodations your pet needs. I’ll treat your pet like my own and keep you updated so you can feel confident they’re in good hands! As a current college student, I have a flexible schedule that gives me plenty of time for walks, drop-ins, feeding, playtime, and pet sitting throughout the day. I’m happy to work around your pet’s usual routine and make sure they get the care and attention they’re used to. In addition to pet sitting, I have 8 years of experience babysitting and house sitting for multiple families. I understand how much trust it takes to leave your pets and home in someone else’s care, so I always treat both with the same respect and attention I would want for my own. I’m responsible, communicative, and happy to follow any routines, instructions, or house rules you provide. I also have flexibility to care for small pets in my own home for short period of time.
“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!”
“Jennifer was available for a last minute drop in visit and we are so glad she was! Our pup Seymour enjoyed his time with her and we appreciated the pictures and updates.”
About: I've taken care of dogs and cats my whole life, whether my own family's pets or friends, coworkers, and neighbors'. From puppies to seniors, I have always been dedicated to pet's comfort, safety, and joy, as well as open communication with pet parents about their babies while they're away. I have a lot of experience with senior dogs, helping them take medication or move around despite mobility difficulties, and know that even if they can't get up and play as much as they used to, they still need as much love and attention as their younger counterparts. I'm currently a graduate student, so my class schedule takes up the majority of my time on Tuesdays, Thursdays, and Fridays. On Mondays and Wednesdays I have a brief shift on campus, but am available before (8-10am) or after (1-9pm), but am completely free on weekends. When staying at a client's home, I am happy to provide play, care, and cuddles to the pets I am watching. Whether they need crating, medication, extra mobility help or just a little extra patience while they get used to a new person, I have lots of experience with pets of all ages, shapes, sizes and personalities.
“Anastasia was fantastic! She went out of her way to make sure our little scaredy cat Jake was super comfortable, and even went back to double-check on his comfort. She also was very communicative and prompt. And even brought in our mail! We will definitely be asking her for her services again! She’s wonderful!”
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 have a super open availability this summer, with more than enough time for late nights, early mornings, and overnight work! I have reliable transportation and a super free schedule to care for furry friends! 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.
“Katherine was attentive, communicative and overall very experienced with animals! She sent pictures and followed all our directions. She even went above and beyond by leaving ice cubes in our cats’ water because it was a hot day - such a nice touch. We have a super shy cat who usually doesn’t come out of hiding for strangers but he was out and about with Katherine! Will be hiring her again.”
“Megan took very good care of our dog Kaya. We hope to have her come back for future drop-in visits on the weekend. We really appreciated the detailed comments and several photos, letting us know that Kaya was doing well. Thanks!”
“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!”
About: Along with growing up having two large dogs and walking them every day, I have been taking care of cats since I was 14 years old! I’ve helped with training my own puppy and have cat-sitted for young, old, and even diabetic little guys. I am about to begin Graduate School to be a Librarian at Simmons College and have time before and after my classes throughout the week. I love all animals and am happy to play and run with them outside. They will feel nothing but love and care from me when we spend time together outside or in your home!
“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 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.
“Yui is an excellent sitter! Teddy warmed up to her right away, and I had no concerns about leaving him in her care. You can tell she really loves animals and put real care into watching after them.”
“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!!!”
The median cost per visit for dog sitting in Jamaica Plain is $25
Dog parents share their Rover experiences - Jamaica Plain
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.
Ann-Marie was absolutely amazing ! She was so loving and kind to my 2 golden retrievers. From the moment she walked in, she was playing with the dogs and it was obvious she loves animals. It was such peace of mind knowing my 2 dogs were being cared for so warmly. Ann-Marie went above and beyond and I couldn’t recommend her more. She gave great updates , sent pictures and exceeded what I had hoped for. So grateful to have found her !
Zoe is absolutely amazing. I can tell she genuinely cares about my pup and loves dogs. Zoe is responsive and even writes a detailed report of what they did and how he was behaving. She also takes so many cute pictures every time! Absolutely love having her take care of my pup :)
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 $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.
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